CYP2C19

Summary

CYP2C19 (cytochrome P450 family 2 subfamily C member 19, HGNC:2621) is a protein-coding gene on chromosome 10q23.33, encoding Cytochrome P450 2C19 (P33261). A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA).

This gene encodes a member of the cytochrome P450 superfamily of enzymes. The cytochrome P450 proteins are monooxygenases which catalyze many reactions involved in drug metabolism and synthesis of cholesterol, steroids and other lipids. This protein localizes to the endoplasmic reticulum and is known to metabolize many xenobiotics, including the anticonvulsive drug mephenytoin, omeprazole, diazepam and some barbiturates. Polymorphism within this gene is associated with variable ability to metabolize mephenytoin, known as the poor metabolizer and extensive metabolizer phenotypes. The gene is located within a cluster of cytochrome P450 genes on chromosome 10q24.

Source: NCBI Gene 1557 — RefSeq curated summary.

At a glance

• GWAS associations: 21
• Clinical variants (ClinVar): 77 total
• Druggable target: yes — 326 molecules with ChEMBL bioactivity
• MANE Select transcript: NM_000769

Identifiers

Gene identifiers

Field	Value
HGNC ID	HGNC:2621
Approved symbol	CYP2C19
Name	cytochrome P450 family 2 subfamily C member 19
Location	10q23.33
Locus type	gene with protein product
Status	Approved
Aliases	P450IIC19, CPCJ
Ensembl gene	ENSG00000165841
Ensembl biotype	protein_coding
OMIM	124020
Entrez	1557

Gene structure

Transcript identifiers

Ensembl transcripts: 11 — 10 protein_coding, 1 retained_intron

ENST00000371321, ENST00000480405, ENST00000645461, ENST00000883430, ENST00000883431, ENST00000883432, ENST00000883433, ENST00000883434, ENST00000883435, ENST00000883436, ENST00000883437

RefSeq mRNA: 1 — MANE Select: NM_000769 NM_000769

CCDS: CCDS7436

Canonical transcript exons

ENST00000371321 — 9 exons

Exon	Start	End
ENSE00001454938	94852733	94855547
ENSE00002446586	94762681	94762873
ENSE00003516375	94780499	94780659
ENSE00003582934	94849917	94850058
ENSE00003600653	94775058	94775220
ENSE00003660121	94781821	94781997
ENSE00003662051	94820496	94820637
ENSE00003666610	94775390	94775539
ENSE00003670360	94842837	94843024

Expression profiles

Bgee: expression breadth broad, 45 present calls, max score 93.26.

FANTOM5 (CAGE): breadth tissue_specific, TPM avg 0.4978 / max 141.6593, expressed in 24 samples.

FANTOM5 promoters (3 alternative TSS)

Promoter ID	TPM avg	Samples expressed
106344	0.4310	24
106343	0.0460	11
106342	0.0209	7

Top tissues by expression

117 total, by Bgee expression score (0-100, higher = more expressed):

Tissue	Anatomy ID	Expression score	Quality
liver	UBERON:0002107	93.26	gold quality
duodenum	UBERON:0002114	92.82	gold quality
right lobe of liver	UBERON:0001114	92.50	gold quality
lower esophagus mucosa	UBERON:0035834	76.94	gold quality
small intestine	UBERON:0002108	71.60	gold quality
small intestine Peyer’s patch	UBERON:0003454	70.88	gold quality
esophagus mucosa	UBERON:0002469	69.36	gold quality
gall bladder	UBERON:0002110	65.11	gold quality
mucosa of stomach	UBERON:0001199	63.41	gold quality
body of stomach	UBERON:0001161	59.61	gold quality
stomach	UBERON:0000945	59.15	gold quality
mucosa of transverse colon	UBERON:0004991	58.74	gold quality
colonic epithelium	UBERON:0000397	54.59	gold quality
intestine	UBERON:0000160	51.07	gold quality
esophagus	UBERON:0001043	50.82	gold quality
vagina	UBERON:0000996	50.77	gold quality
transverse colon	UBERON:0001157	49.54	gold quality
stromal cell of endometrium	CL:0002255	48.20	gold quality
fundus of stomach	UBERON:0001160	47.81	gold quality
skin of abdomen	UBERON:0001416	47.78	gold quality
zone of skin	UBERON:0000014	46.59	gold quality
tonsil	UBERON:0002372	45.83	silver quality
rectum	UBERON:0001052	45.72	gold quality
skin of leg	UBERON:0001511	45.41	gold quality
endometrium	UBERON:0001295	44.57	gold quality
colon	UBERON:0001155	42.57	gold quality
vermiform appendix	UBERON:0001154	42.39	gold quality
islet of Langerhans	UBERON:0000006	42.16	gold quality
olfactory segment of nasal mucosa	UBERON:0005386	41.50	silver quality
sural nerve	UBERON:0015488	40.47	gold quality

Single-cell (SCXA)

Detected in 2 experiment(s), a significant marker in 2.

Experiment	Marker?	Max mean expression
E-MTAB-6678	yes	53.69
E-ANND-3	yes	11.71

Regulation

Is transcription factor: no

Upstream regulators (CollecTRI, top): ATF2, ESR1, FOXA3, FOXC1, GATA2, GATA4, HNF4A, NR1I2, NR1I3, NR3C1, RORA, RORC

miRNA regulators (miRDB)

27 targeting CYP2C19, top 30 by miRDB confidence (max_score; target_count = how many genes the miRNA targets in total — lower means more specific):

miRNA	Max score	Avg score	miRNA target_count
HSA-MIR-3617-3P	99.98	67.86	918
HSA-MIR-507	99.97	70.11	1915
HSA-MIR-557	99.96	70.01	1640
HSA-MIR-4725-3P	99.96	69.53	2520
HSA-MIR-6780B-5P	99.96	69.60	2562
HSA-MIR-2110	99.96	66.68	1930
HSA-MIR-369-3P	99.85	70.52	2264
HSA-MIR-4668-5P	99.79	70.58	3782
HSA-MIR-379-3P	99.69	69.60	1524
HSA-MIR-411-3P	99.69	69.63	1524
HSA-MIR-7157-5P	99.66	69.33	1829
HSA-MIR-4310	99.59	68.84	2527
HSA-MIR-5584-5P	99.49	68.22	2814
HSA-MIR-1275	99.47	67.90	2749
HSA-MIR-7515	99.31	68.22	1795
HSA-MIR-4520-2-3P	99.14	69.28	1009
HSA-MIR-4478	99.07	65.16	2320
HSA-MIR-1843	98.97	66.07	838
HSA-MIR-4802-5P	98.97	66.26	833
HSA-MIR-138-2-3P	98.91	68.33	1643
HSA-MIR-891A-3P	98.05	67.99	970
HSA-MIR-4443	98.02	66.25	1928
HSA-MIR-4665-5P	97.91	67.69	1536
HSA-MIR-7112-3P	97.67	68.77	948
HSA-MIR-4776-5P	97.14	66.63	405
HSA-MIR-3675-5P	95.90	65.80	474
HSA-MIR-6890-5P	92.89	65.83	442

Literature-anchored findings (GeneRIF, showing 34)

• concordance between the in vitro activity of OMZ hydroxylase and the CYP2C19 genotype in North Indians (PMID:11791894)
• Expression and induction in primary culture of hepatocytes (PMID:12130704)
• contributes to the biotransformation and E-and Z-doxepin in healthy volunteers (PMID:12360109)
• CYP2C19 polymorphism is associated with pharmacological effects of thalidomide in prostatic neoplasms (PMID:12642692)
• There is an association between blood carisoprodol: meprobamate concentration ratios and CYP2C19 genotype. (PMID:12835613)
• Using a chiral micellar electrokinetic capillary chromatography assay, the aromatic hydroxylation of Mephenytoin catalyzed by CYP2C19 was confirmed to be highly stereoselective; CYP2C19 also provided enhanced formation of R-EDDP from methadone (PMID:12900870)
• CYP2D6 and CYP2C19 do not significantly contribute to the metabolism of Methaqualone; although interindividual differences in the monitored metabolic patterns were noted, no marked difference could be related to a CYP2D6 or CYP2C19 polymorphism. (PMID:12900872)
• The prevalence of mutations of allelic variant predict genotype frequency in the croatian populations. (PMID:12950145)
• Analysis of the Sepik populations of Papua New Guinea suggest an increase of CYP2C19 null allele frequencies during the colonization of Melanesia. (PMID:14583683)
• The ontogeny of CYP2C9 and -2C19 were dissimilar among both fetal and 0- to 5-months postnatal samples, implying different developmental regulatory mechanisms. (PMID:14634042)
• P. 497: “Poor CYP2C19 metabolizers are rate in Italy…” P. 494: “…[I]n the Japanese population, … poor metabolizers of the CYP2C19 are frequently observed.” (PMID:14998561)
• CYP2C19, an isoform contributing to the clearance of S-mephenytoin, diazepam, omeprazole, proguanil, citalopram, R-warfarin and many antidepressants." (PMID:15177309)
• CYP2C19 may participate in the activation of procarcinogen of esophagus cancer, stomach cancer and lung cancer, but may involve in the detoxification of carcinogens of bladder cancer. (PMID:15222046)
• Polymorphism of CYP2C19 gene is involved in the metabolism of various drugs used clinically. (PMID:15776277)
• SNPs of CYP2C19 and 23S rRNA of H pylori using RUT-positive gastric mucosal samples could be predictable determinants for H pylori eradication by triple therapy. (PMID:15952098)
• In renal-transplant recipients who are CYP2C19 extensive metabolizers, there is less stereoselective difference in the pharmacokinetics disposition the enantiomers of rabeprazole than those of lansoprazole. (PMID:16012079)
• influence of CYP2C9, CYP2C19 and ABCB1 genetic polymorphisms on phenytoin metabolism in a Black population (PMID:16220110)
• Some of the elderly homozygous extensive metabolizers (EMs), as well as heterozygous EMs, have a metabolic activity similar to poor metabolizers, and the CYP2C19 genotype may not be as useful as phenotyping in the elderly. (PMID:16231968)
• CYP2C19 genotype is unrelated to the esomeprazole-induced healing of gastroesophageal reflux disease. (PMID:16338278)
• Results show that the CYP2C19 genotype affects diazepam pharmacokinetics and emergence from general anesthesia. (PMID:16338280)
• CYP2C19 mRNA expression is highest in hepatocarcinoma tissue, moderate in adjacent normal liver tissue, and absent in other cancer tissues and their adjacent normal tissues. (PMID:16641871)
• the CYP2C19*2 loss-of-function allele is associated with a marked decrease in platelet responsiveness to clopidogrel in young healthy male volunteers (PMID:16772608)
• The constructs, CYP2C9/BMR, CYP2C19/BMR and CYP3A4/BMR are well expressed in Escherichia coli as holo proteins. (PMID:16862439)
• Analysis of CYP2C19 enzyme genotype indicated the patient was a homozygous extensive metabolizer, considered a poor responder for omeprazole treatment for duodenal ulcer. (PMID:16908943)
• The poor metabolizers phenotype and the frequencies of CYP2C19 defective alleles, particularly CYP2C19*3 among these three Southeast Asian ethnics appeared to be lower than other Asian populations. (PMID:16946555)
• The present study thus suggests that the CYP2C19 polymorphism affects personality traits of Japanese females. (PMID:17052843)
• no evidence to support CYP2C19 genetic polymorphisms as predictable potential risk factors for drug-induced idiosyncratic liver injury (PMID:17279092)
• No relationship between CYP2C19 polymorphism and susceptibility to gastric and colorectal cancers. (PMID:17290075)
• a significant association between CYP2C19 activity and harm avoidance is present in Japanese (PMID:17357148)
• In CYP2C19 homozygous extensive metabolizers, the acid-suppressive effect of omeprazole is no potent compared to heterozygous or poor metabolizers. (PMID:17410461)
• An inhibition assay was developed and validated for CYP2C19 in liver microsomes. (PMID:17418993)
• CYP219 has been demonstrated to be involved in the metabolism of voriconazole. (PMID:17433262)
• Study shows an obvious relationship between CYP2C19 genotype and omeprazole hydroxylation phenotype in the different ethnic populations of China. (PMID:17439410)
• results suggest that Ser51Gly substitution in CYP2C19.19 decreases the affinity toward S-mephenytoin of CYP2C19 enzyme, and imply that the genetic polymorphism of CYP2C19*19 also causes variations in the clinical response to drugs metabolized by CYP2C19 (PMID:17455109)

Cross-species orthologs

0 orthologs

Paralogs (15): CYP2W1 (ENSG00000073067), CYP2D6 (ENSG00000100197), CYP2C18 (ENSG00000108242), CYP2E1 (ENSG00000130649), CYP2J2 (ENSG00000134716), CYP2C9 (ENSG00000138109), CYP2C8 (ENSG00000138115), CYP2U1 (ENSG00000155016), CYP2S1 (ENSG00000167600), CYP2R1 (ENSG00000186104), CYP2B6 (ENSG00000197408), CYP2F1 (ENSG00000197446), CYP2A13 (ENSG00000197838), CYP2A7 (ENSG00000198077), CYP2A6 (ENSG00000255974)

Protein

Protein identifiers

Cytochrome P450 2C19 — P33261 (reviewed: P33261)

Alternative names: (R)-limonene 6-monooxygenase, (S)-limonene 6-monooxygenase, (S)-limonene 7-monooxygenase, CYPIIC17, CYPIIC19, Cytochrome P450-11A, Cytochrome P450-254C, Fenbendazole monooxygenase (4’-hydroxylating), Mephenytoin 4-hydroxylase

All UniProt accessions (2): A0A087X125, P33261

UniProt curated annotations — full annotation on UniProt →

Function. A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH–hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position. Catalyzes the epoxidation of double bonds of PUFA. Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol. Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4’ position.

Subcellular location. Endoplasmic reticulum membrane. Microsome membrane.

Induction. P450 can be induced to high levels in liver and other tissues by various foreign compounds, including drugs, pesticides, and carcinogens.

Pathway. Lipid metabolism; fatty acid metabolism. Terpene metabolism; (4R)-limonene degradation.

Polymorphism. Genetic variation in CYP2C19 is responsible for poor drug metabolism [MIM:609535]. Individuals can be characterized as either extensive metabolizers (EM) or poor metabolizers (PM). The PM phenotype is inherited in an autosomal recessive manner, with the EM phenotype comprising both homozygous dominant and heterozygote genotypes. There are marked interracial differences in the frequency of this polymorphism. Poor metabolizers represent 2-5% of Caucasians, 13-23% of Asian populations, and as many as 38-79% of individuals of some of the islands of Polynesia and Micronesia. At least 38 different alleles are known including CYP2C191A, CYP2C191B, CYP2C191C, CYP2C192A (CYP2C19m1 or CYP2C19m1A), CYP2C192B (CYP2C19m1B), CYP2C192C (CYP2C1921), CYP2C193A (CYP2C19m2), CYP2C193B (CYP2C1920), CYP2C194 (CYP2C19m3), CYP2C195A (CYP2C19m4), CYP2C195B, CYP2C196, CYP2C197, CYP2C198, CYP2C199, CYP2C1910, CYP2C1911 CYP2C1912, CYP2C1913, CYP2C1914 CYP2C1915, CYP2C1916, CYP2C1918 and CYP2C1919. Defective CYP2C192 and CYP2C193 alleles are characterized by a splice mutation and a stop codon, respectively, and account for most of the PM alleles. The sequence shown is that of allele CYP2C19*1A.

Similarity. Belongs to the cytochrome P450 family.

RefSeq proteins (1): NP_000760* (*=MANE)

Domains & families (InterPro)

ID	Name	Type
IPR001128	Cyt_P450	Family
IPR002401	Cyt_P450_E_grp-I	Family
IPR017972	Cyt_P450_CS	Conserved_site
IPR036396	Cyt_P450_sf	Homologous_superfamily
IPR050182	Cytochrome_P450_fam2	Family

Pfam: PF00067

Enzyme classification (BRENDA):

• EC 1.14.14.75 — fenbendazole monooxygenase (4’-hydroxylating) (BRENDA: 1 organisms, 1 substrates, 0 inhibitors, 0 Km, 0 kcat entries)

Catalyzed reactions (Rhea), 12 shown:

• an organic molecule + reduced [NADPH–hemoprotein reductase] + O2 = an alcohol + oxidized [NADPH–hemoprotein reductase] + H2O + H(+) (RHEA:17149)
• (4S)-limonene + reduced [NADPH–hemoprotein reductase] + O2 = (1S,5R)-carveol + oxidized [NADPH–hemoprotein reductase] + H2O + H(+) (RHEA:17945)
• (4R)-limonene + reduced [NADPH–hemoprotein reductase] + O2 = (1R,5S)-carveol + oxidized [NADPH–hemoprotein reductase] + H2O + H(+) (RHEA:18957)
• (4S)-limonene + reduced [NADPH–hemoprotein reductase] + O2 = (4S)-perillyl alcohol + oxidized [NADPH–hemoprotein reductase] + H2O + H(+) (RHEA:23432)
• (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH–hemoprotein reductase] + O2 = 19-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH–hemoprotein reductase] + H2O + H(+) (RHEA:39759)
• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH–hemoprotein reductase] + O2 = (17R,18S)-epoxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + oxidized [NADPH–hemoprotein reductase] + H2O + H(+) (RHEA:39779)
• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + reduced [NADPH–hemoprotein reductase] + O2 = 19-hydroxy-(5Z,8Z,11Z,14Z,17Z)-eicosapentaenoate + oxidized [NADPH–hemoprotein reductase] + H2O + H(+) (RHEA:39787)
• (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH–hemoprotein reductase] + O2 = (14R,15S)-epoxy-(5Z,8Z,11Z)-eicosatrienoate + oxidized [NADPH–hemoprotein reductase] + H2O + H(+) (RHEA:49860)
• (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH–hemoprotein reductase] + O2 = (11S,12R)-epoxy-(5Z,8Z,14Z)-eicosatrienoate + oxidized [NADPH–hemoprotein reductase] + H2O + H(+) (RHEA:49876)
• (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH–hemoprotein reductase] + O2 = (11R,12S)-epoxy-(5Z,8Z,14Z)-eicosatrienoate + oxidized [NADPH–hemoprotein reductase] + H2O + H(+) (RHEA:49880)
• (5Z,8Z,11Z,14Z)-eicosatetraenoate + reduced [NADPH–hemoprotein reductase] + O2 = (8R,9S)-epoxy-(5Z,11Z,14Z)-eicosatrienoate + oxidized [NADPH–hemoprotein reductase] + H2O + H(+) (RHEA:49884)
• (5Z,8Z,11Z)-eicosatrienoate + reduced [NADPH–hemoprotein reductase] + O2 = 19-hydroxy-(5Z,8Z,11Z)-eicosatrienoate + oxidized [NADPH–hemoprotein reductase] + H2O + H(+) (RHEA:50076)

UniProt features (62 total): helix 22, sequence variant 18, strand 12, turn 8, chain 1, binding site 1

Structure

Experimental structures (PDB)

1 structures.

PDB	Method	Resolution (Å)
4GQS	X-RAY DIFFRACTION	2.87

Predicted structure (AlphaFold)

Model	pLDDT	Fraction very-high
AF-P33261-F1	94.24	0.86

Functional residue map

Curated UniProt residues grouped by drug-discovery relevance — catalytic, ligand-binding, modification, and mutation-validated positions. Source: UniProtKB sequence features.

Ligand- & substrate-binding residues (1): 435 (axial binding residue)

Function

Pathways and Gene Ontology

Reactome pathways

5 pathways

ID	Pathway
R-HSA-211981	Xenobiotics
R-HSA-211999	CYP2E1 reactions
R-HSA-2142670	Synthesis of epoxy (EET) and dihydroxyeicosatrienoic acids (DHET)
R-HSA-2142816	Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE)
R-HSA-9749641	Aspirin ADME

MSigDB gene sets: 130 (showing top): GSE45365_NK_CELL_VS_CD11B_DC_UP, MODULE_93, REACTOME_BIOLOGICAL_OXIDATIONS, GOMF_OXIDOREDUCTASE_ACTIVITY_ACTING_ON_PAIRED_DONORS_WITH_INCORPORATION_OR_REDUCTION_OF_MOLECULAR_OXYGEN, GOBP_LONG_CHAIN_FATTY_ACID_METABOLIC_PROCESS, GOBP_MONOCARBOXYLIC_ACID_METABOLIC_PROCESS, MORF_RAD51L3, WIEMANN_TELOMERE_SHORTENING_AND_CHRONIC_LIVER_DAMAGE_DN, MODULE_379, MORF_PRKCA, CAIRO_HEPATOBLASTOMA_DN, GOBP_LIPID_METABOLIC_PROCESS, GOBP_ORGANIC_ACID_METABOLIC_PROCESS, MODULE_88, MODULE_242

GO Biological Process (11): long-chain fatty acid metabolic process (GO:0001676), xenobiotic metabolic process (GO:0006805), steroid metabolic process (GO:0008202), monoterpenoid metabolic process (GO:0016098), epoxygenase P450 pathway (GO:0019373), xenobiotic catabolic process (GO:0042178), omega-hydroxylase P450 pathway (GO:0097267), lipid metabolic process (GO:0006629), fatty acid metabolic process (GO:0006631), terpenoid metabolic process (GO:0006721), monocarboxylic acid metabolic process (GO:0032787)

GO Molecular Function (14): monooxygenase activity (GO:0004497), iron ion binding (GO:0005506), steroid hydroxylase activity (GO:0008395), oxidoreductase activity (GO:0016491), oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen (GO:0016712), (S)-limonene 6-monooxygenase activity (GO:0018675), (S)-limonene 7-monooxygenase activity (GO:0018676), oxygen binding (GO:0019825), enzyme binding (GO:0019899), heme binding (GO:0020037), (R)-limonene 6-monooxygenase activity (GO:0052741), long-chain fatty acid omega-1 hydroxylase activity (GO:0120319), oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen (GO:0016705), metal ion binding (GO:0046872)

GO Cellular Component (6): cytoplasm (GO:0005737), endoplasmic reticulum membrane (GO:0005789), plasma membrane (GO:0005886), intracellular membrane-bounded organelle (GO:0043231), endoplasmic reticulum (GO:0005783), membrane (GO:0016020)

Reactome top-level categories

Rollup of top-4 pathways:

Category	Pathways
Arachidonate metabolism	2
Cytochrome P450 - arranged by substrate type	1
Xenobiotics	1
Drug ADME	1

GO top-level categories

Rollup of top GO terms by namespace:

Category	Terms
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen	3
limonene monooxygenase activity	3
lipid metabolic process	2
arachidonate metabolic process	2
oxidoreductase activity	2
monooxygenase activity	2
intracellular anatomical structure	2
cellular anatomical structure	2
fatty acid metabolic process	1
metabolic process	1
cellular response to xenobiotic stimulus	1
terpenoid metabolic process	1
xenobiotic metabolic process	1
catabolic process	1
primary metabolic process	1
monocarboxylic acid metabolic process	1
isoprenoid metabolic process	1
carboxylic acid metabolic process	1
transition metal ion binding	1
catalytic activity	1
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen	1
small molecule binding	1
protein binding	1
tetrapyrrole binding	1
fatty acid omega-1 hydroxylase activity	1
cation binding	1
organelle membrane	1
nuclear outer membrane-endoplasmic reticulum membrane network	1
endoplasmic reticulum subcompartment	1
membrane	1
cell periphery	1
membrane-bounded organelle	1
intracellular organelle	1
cytoplasm	1
endomembrane system	1
intracellular membrane-bounded organelle	1

Protein interactions and networks

STRING

0 interactions, top by confidence (×1000):

IntAct

5 interactions, top by confidence:

A	B	Type	Score
CYP2C9	TOMM40	psi-mi:“MI:0914”(association)	0.530
CYP2C9	CYP2C19	psi-mi:“MI:0914”(association)	0.530
CYP2C19	MFN2	psi-mi:“MI:0914”(association)	0.350

BioGRID (7): CYP2C19 (Affinity Capture-MS), MFN2 (Affinity Capture-MS), CYP2C19 (Reconstituted Complex), CYP2C18 (Affinity Capture-MS), CYP2C19 (Affinity Capture-MS), EEA1 (Cross-Linking-MS (XL-MS)), CYP2C19 (Reconstituted Complex)

ESM2 similar proteins: E9Q5K4, O55071, O62671, P00179, P00180, P00181, P00182, P05178, P05179, P05180, P05181, P08683, P11371, P11509, P11711, P11712, P12790, P13107, P15123, P15392, P17666, P19225, P20678, P20812, P20814, P20852, P20853, P24454, P24470, P33260, P33261, P33263, P33264, P33265, P33272, P33273, P56593, P56594, P56654, P56655

Diamond homologs: A0A087X1C5, E9Q5K4, F1Q8C3, O18809, O18992, O35293, O46658, O54749, O54750, O55071, O62671, O93297, P00176, P00178, P00179, P00180, P00181, P00182, P04167, P05178, P05179, P05180, P05181, P08682, P08683, P10610, P10632, P10633, P10634, P10635, P11371, P11712, P11714, P12789, P12790, P12791, P12938, P12939, P15123, P17666

SIGNOR signaling

0 interactions.

Disease & clinical

Clinical variants and AI predictions

ClinVar

77 variants total. Per-class counts are floors (≥ shown; pagination cap):

Classification	Count (floor)
Pathogenic	0
Likely pathogenic	0
Uncertain significance	47
Likely benign	6
Benign	7

Top pathogenic / likely-pathogenic (0)

SpliceAI

2202 predictions. Top by Δscore:

Variant	Effect	Δscore
10:94775052:TTCTA:T	acceptor_loss	1.0000
10:94775053:TCTA:T	acceptor_loss	1.0000
10:94775054:CTA:C	acceptor_loss	1.0000
10:94775055:TAGC:T	acceptor_loss	1.0000
10:94775055:TAGCT:T	acceptor_loss	1.0000
10:94775056:A:AG	acceptor_gain	1.0000
10:94775056:AGC:A	acceptor_loss	1.0000
10:94775057:G:GG	acceptor_gain	1.0000
10:94775057:G:GT	acceptor_gain	1.0000
10:94775057:G:T	acceptor_loss	1.0000
10:94775057:GC:G	acceptor_gain	1.0000
10:94775057:GCT:G	acceptor_gain	1.0000
10:94775057:GCTC:G	acceptor_gain	1.0000
10:94775057:GCTCT:G	acceptor_gain	1.0000
10:94775092:ATTTT:A	acceptor_gain	1.0000
10:94775096:T:TA	acceptor_gain	1.0000
10:94775218:TTGG:T	donor_loss	1.0000
10:94775219:TGGTA:T	donor_loss	1.0000
10:94775220:GGTA:G	donor_loss	1.0000
10:94775221:G:GA	donor_loss	1.0000
10:94775221:G:GG	donor_gain	1.0000
10:94775389:GGA:G	acceptor_gain	1.0000
10:94775500:G:GT	donor_gain	1.0000
10:94775516:TGGAG:T	donor_gain	1.0000
10:94775517:GGAGG:G	donor_gain	1.0000
10:94775521:GAGT:G	donor_gain	1.0000
10:94775524:T:G	donor_gain	1.0000
10:94775537:AGGG:A	donor_loss	1.0000
10:94775538:GG:G	donor_gain	1.0000
10:94775539:GG:G	donor_gain	1.0000

AlphaMissense

3253 scored. Top likely-pathogenic:

Variant	Protein change	am_pathogenicity
10:94850049:T:C	F428L	0.993
10:94850051:C:A	F428L	0.993
10:94850051:C:G	F428L	0.993
10:94842923:G:C	A350P	0.987
10:94849968:T:C	F401L	0.986
10:94849970:T:A	F401L	0.986
10:94849970:T:G	F401L	0.986
10:94842946:A:C	R357S	0.984
10:94842946:A:T	R357S	0.984
10:94850001:T:C	F412L	0.983
10:94850003:T:A	F412L	0.983
10:94850003:T:G	F412L	0.983
10:94842945:G:C	R357T	0.978
10:94849927:T:A	I387K	0.977
10:94775180:A:C	R97S	0.974
10:94775180:A:T	R97S	0.974
10:94775434:T:C	F126L	0.974
10:94775436:C:A	F126L	0.974
10:94775436:C:G	F126L	0.974
10:94762828:T:A	N41K	0.972
10:94762828:T:G	N41K	0.972
10:94775453:G:C	R132P	0.972
10:94820568:G:T	G298W	0.972
10:94852744:T:C	C435R	0.971
10:94852777:T:C	F446L	0.971
10:94852779:T:A	F446L	0.971
10:94852779:T:G	F446L	0.971
10:94775429:G:C	R124P	0.968
10:94849986:T:C	F407L	0.968
10:94849988:T:A	F407L	0.968

dbSNP variants (sampled 300 via entrez): RS1000025258 (10:94813376 C>A), RS1000026535 (10:94769837 C>T), RS1000039693 (10:94779679 G>A), RS1000088770 (10:94844924 G>A), RS1000118223 (10:94828953 G>A,T), RS1000167174 (10:94796552 G>A,C,T), RS1000177826 (10:94831540 A>T), RS1000217510 (10:94833998 G>C,T), RS1000264474 (10:94832224 A>G), RS1000266480 (10:94840028 T>A,G), RS1000273235 (10:94823564 T>C), RS1000294244 (10:94824980 A>G), RS1000327680 (10:94770506 G>A), RS1000359262 (10:94800531 G>A,T), RS1000377811 (10:94774757 G>A,T)

Disease associations

OMIM: gene MIM:124020 | disease phenotypes:

GenCC curated gene-disease

Mondo (2): acute coronary syndrome (MONDO:0005542), primary ovarian failure (MONDO:0005387)

Orphanet (1): NON RARE IN EUROPE: Primary ovarian failure (Orphanet:619)

HPO phenotypes

0 total (0 of 0 shown, HPO-id order):

GWAS associations

21 associations (top):

Study	Trait	p-value
GCST000436_2	Acenocoumarol maintenance dosage	3.000000e-07
GCST000467_1	Response to clopidogrel therapy	2.000000e-13
GCST002061_1	Warfarin maintenance dose	5.000000e-12
GCST002549_1	Response to serotonin reuptake inhibitors in major depressive disorder (plasma drug and metabolite levels)	2.000000e-16
GCST002549_2	Response to serotonin reuptake inhibitors in major depressive disorder (plasma drug and metabolite levels)	4.000000e-09
GCST004264_1	Clopidogrel active metabolite levels	1.000000e-14
GCST004266_1	Response to clopidogrel therapy	1.000000e-16
GCST006206_3	Thiopurine-induced alopecia in inflammatory bowel disease	1.000000e-06
GCST006227_10	Diastolic blood pressure	3.000000e-07
GCST006231_40	Mean arterial pressure	1.000000e-06
GCST006249_39	Serum metabolite levels	7.000000e-23
GCST006249_40	Serum metabolite levels	7.000000e-21
GCST006249_64	Serum metabolite levels	4.000000e-26
GCST007094_20	Diastolic blood pressure	2.000000e-06
GCST007096_250	Pulse pressure	2.000000e-06
GCST007099_101	Systolic blood pressure	1.000000e-09
GCST007267_55	Systolic blood pressure	2.000000e-09
GCST007684_2	Plasma clozapine-norclozapine ratio in treatment-resistant schizophrenia	5.000000e-14
GCST010563_2	Clozapine-to-N-desmethylclozapine metabolic ratio in schizophrenia	1.000000e-16
GCST90000025_450	Appendicular lean mass	5.000000e-33
GCST90013406_82	Liver enzyme levels (alkaline phosphatase)	6.000000e-20

EFO canonical traits (10, from GWAS)

EFO ID	Trait name
EFO:0005658	response to selective serotonin reuptake inhibitor
EFO:0007966	clopidogrel metabolite measurement
EFO:0006336	diastolic blood pressure
EFO:0006340	mean arterial pressure
EFO:0005763	pulse pressure measurement
EFO:0006335	systolic blood pressure
EFO:0600040	plasma clozapine-to-N-desmethylclozapine ratio measurement
EFO:0600042	serum clozapine-to-N-desmethylclozapine ratio measurement
EFO:0004980	appendicular lean mass
EFO:0004533	alkaline phosphatase measurement

MeSH disease descriptors (2)

Descriptor	Name	Tree numbers
D054058	Acute Coronary Syndrome	C14.280.647.124; C14.907.585.124
D016649	Primary Ovarian Insufficiency	C12.050.351.500.056.630.750; C12.100.250.056.630.750; C19.391.630.750

Drugs & pharmacology

Drug and pharmacology data

Is drug target: yes

ChEMBL targets (3): CHEMBL3622 (SINGLE PROTEIN), CHEMBL4523986 (PROTEIN FAMILY), CHEMBL6066546 (PROTEIN FAMILY)

Molecules with ChEMBL bioactivity

326 molecules (phase ≥1), by development phase (incl. off-target/promiscuous compounds). Patent mentions across the top 20 by phase: 799,051 (via chembl_molecule»patent_compound — counts attach to the compound, not the gene–compound relationship, so off-target/promiscuous molecules can dominate).

Molecule	Name	Phase	Patents
CHEMBL1008	BEPRIDIL	4	11,776
CHEMBL1018	DIENESTROL	4	5,607
CHEMBL104	CLOTRIMAZOLE	4	56,325
CHEMBL1057	FLUORESCEIN	4	329,940
CHEMBL106	FLUCONAZOLE	4	58,942
CHEMBL107	COLCHICINE	4	93,932
CHEMBL1071	OXAPROZIN	4	51,044
CHEMBL1073	GLIPIZIDE	4	42,268
CHEMBL1089	PHENELZINE	4	18,793
CHEMBL110691	CHLORMADINONE ACETATE	4	9,747
CHEMBL1109	SULFAPHENAZOLE	4	4,065
CHEMBL1170	TESTOSTERONE PROPIONATE	4	17,619
CHEMBL1175	DULOXETINE	4	28,527
CHEMBL1196	PROPARACAINE	4	12,973
CHEMBL1200326	NICARDIPINE HYDROCHLORIDE	4	3,903
CHEMBL1200419	MOLINDONE HYDROCHLORIDE	4	4,907
CHEMBL1200604	TROPICAMIDE	4	14,498
CHEMBL1200623	ETHYLESTRENOL	4	1,795
CHEMBL1200761	CHLOROTRIANISENE	4	23,246
CHEMBL1201146	NORETHINDRONE ACETATE	4	9,144
CHEMBL1201256	TRIMETHOBENZAMIDE	4
CHEMBL1221	SULCONAZOLE	4
CHEMBL1231	OXYBUTYNIN	4
CHEMBL1237135	MAPROTILINE HYDROCHLORIDE	4
CHEMBL1256786	FORMOTEROL	4
CHEMBL1256841	NIALAMIDE	4
CHEMBL1262	OXICONAZOLE	4
CHEMBL1274	NILUTAMIDE	4
CHEMBL127516	BUTAMBEN	4
CHEMBL12856	INAMRINONE	4

PharmGKB: 1 entry (VIP=true, CPIC=true)

PharmGKB clinical annotations

77 annotations.

Variant	Type	Level	Drugs	Phenotypes
CYP2C191, CYP2C1914, CYP2C19*23	Metabolism/PK	3	clopidogrel
CYP2C191, CYP2C1917	Toxicity	3	clopidogrel	Acute coronary syndrome;Coronary Artery Disease;Hemorrhage;Myocardial Infarction
CYP2C191, CYP2C1917	Toxicity	3	prasugrel	Acute coronary syndrome
CYP2C191, CYP2C1923, CYP2C1929, CYP2C1930, CYP2C1931, CYP2C1933	Metabolism/PK	3	omeprazole
CYP2C191, CYP2C192	Metabolism/PK	1A	trimipramine
CYP2C191, CYP2C192	Metabolism/PK	1A	doxepin
CYP2C191, CYP2C192	Efficacy	3	tacrolimus	Kidney Transplantation
CYP2C191, CYP2C192	Dosage	3	tacrolimus	Kidney Transplantation
CYP2C191, CYP2C192	Other	3	bupropion
CYP2C191, CYP2C192	Metabolism/PK	3	dipyrone
CYP2C191, CYP2C192	Metabolism/PK	4	carisoprodol
CYP2C191, CYP2C192	Efficacy	4	venlafaxine
CYP2C191, CYP2C192, CYP2C19*16	Metabolism/PK	3	methylphenobarbital
CYP2C191, CYP2C192, CYP2C19*17	Efficacy,Metabolism/PK	3	tamoxifen	Breast Neoplasms
CYP2C191, CYP2C192, CYP2C19*17	Toxicity	3	3;4-methylenedioxymethamphetamine
CYP2C191, CYP2C192, CYP2C19*17	Metabolism/PK	3	3;4-methylenedioxymethamphetamine
CYP2C191, CYP2C192, CYP2C19*17	Metabolism/PK	3	progesterone
CYP2C191, CYP2C192, CYP2C19*3	Metabolism/PK	1A	dexlansoprazole
CYP2C191, CYP2C192, CYP2C19*3	Efficacy	3	clobazam	Epilepsy
CYP2C191, CYP2C192, CYP2C19*3	Dosage	3	clobazam	Epilepsy
CYP2C191, CYP2C192, CYP2C19*3	Metabolism/PK	3	esomeprazole
CYP2C191, CYP2C192, CYP2C19*3	Metabolism/PK	3	diazepam
CYP2C191, CYP2C192, CYP2C19*3	Efficacy	3	sulfonamides;urea derivatives	Diabetes Mellitus;Type 2
CYP2C191, CYP2C192, CYP2C19*3	Efficacy	3	rabeprazole	Gastroesophageal Reflux;Helicobacter Infections;Peptic Ulcer Disease
CYP2C191, CYP2C192, CYP2C19*3	Efficacy	3	esomeprazole	Gastroesophageal Reflux;Helicobacter Infections
CYP2C191, CYP2C192, CYP2C19*3	Toxicity	4	valproic acid	Epilepsy
CYP2C191, CYP2C192, CYP2C19*3	Metabolism/PK	4	methadone
CYP2C191, CYP2C192, CYP2C19*3	Efficacy	1A	omeprazole	Esophagitis;Gastroesophageal Reflux;Helicobacter Infections;Peptic Ulcer Disease
CYP2C191, CYP2C192, CYP2C19*3	Efficacy	1A	lansoprazole	Gastroesophageal Reflux;Helicobacter Infections
CYP2C191, CYP2C192, CYP2C19*3	Efficacy	1A	pantoprazole	Helicobacter Infections;Ulcer
CYP2C191, CYP2C192, CYP2C19*3	Metabolism/PK	2A	rabeprazole
CYP2C191, CYP2C192, CYP2C19*3	Metabolism/PK	2A	clobazam;norclobazam	Epilepsy
CYP2C191, CYP2C192, CYP2C19*3	Other	3	icotinib
CYP2C191, CYP2C192, CYP2C19*3	Metabolism/PK	3	brivaracetam
CYP2C191, CYP2C192, CYP2C19*3	Dosage	3	warfarin	Atrial Fibrillation
CYP2C191, CYP2C192, CYP2C193, CYP2C1917	Metabolism/PK	1A	voriconazole
CYP2C191, CYP2C192, CYP2C193, CYP2C1917	Efficacy	4	citalopram	Major Depressive Disorder;Obsessive-Compulsive Disorder
CYP2C191, CYP2C192, CYP2C193, CYP2C1917	Efficacy	1A	clopidogrel	Cardiovascular Disease
CYP2C191, CYP2C192, CYP2C193, CYP2C1917	Metabolism/PK	1A	pantoprazole
CYP2C191, CYP2C192, CYP2C193, CYP2C1917	Metabolism/PK	1A	clomipramine	Mental Disorders

PharmGKB variants

96 variants.

Variant	Genes	Level	Score	#Clin annots	Drugs
rs3758580	CYP2C19		0.00	0
rs3758581	CYP2C19		0.00	53
rs3814637	CYP2C19	3	5.25	2	warfarin
rs4244285	CYP2C19	3	6.75	55	cyclophosphamide;doxorubicin;cyclophosphamide;prasugrel;cyclophosphamide;doxorubicin;fluorouracil;venlafaxine;etravirine;nelfinavir
rs4986893	CYP2C19	3	1.50	36	phenytoin;ethambutol;isoniazid;pyrazinamide;rifampin
rs6413438	CYP2C19		0.00	3
rs7902257	CYP2C19		0.00	0
rs11188072	CYP2C19	3	2.00	1	mephenytoin
rs11568732	CYP2C19	3	0.00	1	clopidogrel
rs12248560	CYP2C19	3	2.75	25	mephenytoin;cyclophosphamide;doxorubicin;fluorouracil;phenazepam;busulfan
rs12571421	CYP2C19		0.00	0
rs12768009	CYP2C19	3	0.00	1	nevirapine
rs12769205	CYP2C19		0.00	48
rs17878459	CYP2C19		0.00	0
rs17879685	CYP2C19		0.00	1
rs17882687	CYP2C19		0.00	1
rs17884712	CYP2C19		0.00	3
rs28399504	CYP2C19	3	0.50	3	mephenytoin
rs41291556	CYP2C19		0.00	5
rs55640102	CYP2C19		0.00	0
rs55752064	CYP2C19		0.00	2
rs55948420	CYP2C19		0.00	0
rs56337013	CYP2C19		0.00	3
rs58973490	CYP2C19		0.00	49
rs72552267	CYP2C19		0.00	3
rs72558186	CYP2C19		0.00	1
rs113934938	CYP2C19		0.00	0
rs118203756	CYP2C19		0.00	3
rs118203757	CYP2C19		0.00	2
rs118203759	CYP2C19		0.00	2
rs138142612	CYP2C19		0.00	1
rs140278421	CYP2C19		0.00	1
rs144036596	CYP2C19		0.00	0
rs145119820	CYP2C19	3	1.00	1	mephenytoin
rs145328984	CYP2C19		0.00	1
rs181297724	CYP2C19		0.00	0
rs192154563	CYP2C19		0.00	2
rs370803989	CYP2C19		0.00	1
rs550527959	CYP2C19		0.00	0
rs763625282	CYP2C19		0.00	0

PharmGKB dosing guidelines

37 guidelines.

Source	Drug	Guideline	Dosing?	Recommendation?
CPIC	amitriptyline	Annotation of CPIC Guideline for amitriptyline and CYP2C19, CYP2D6	yes	yes
CPIC	citalopram;escitalopram	Annotation of CPIC Guideline for citalopram, escitalopram and CYP2C19	yes	yes
CPIC	clomipramine	Annotation of CPIC Guideline for clomipramine and CYP2C19, CYP2D6	yes	yes
CPIC	clopidogrel	Annotation of CPIC Guideline for clopidogrel and CYP2C19		yes
CPIC	dexlansoprazole	Annotation of CPIC Guideline for dexlansoprazole and CYP2C19	yes	yes
CPIC	doxepin	Annotation of CPIC Guideline for doxepin and CYP2C19, CYP2D6	yes	yes
CPIC	esomeprazole;rabeprazole	Annotation of CPIC Guideline for esomeprazole, rabeprazole and CYP2C19
CPIC	imipramine	Annotation of CPIC Guideline for imipramine and CYP2C19, CYP2D6	yes	yes
CPIC	lansoprazole;omeprazole;pantoprazole	Annotation of CPIC Guideline for lansoprazole, omeprazole, pantoprazole and CYP2C19	yes	yes
CPIC	sertraline	Annotation of CPIC Guideline for sertraline and CYP2B6, CYP2C19	yes	yes
CPIC	trimipramine	Annotation of CPIC Guideline for trimipramine and CYP2C19, CYP2D6	yes	yes
CPIC	voriconazole	Annotation of CPIC Guideline for voriconazole and CYP2C19	yes	yes
DPWG	amitriptyline	Annotation of DPWG Guideline for amitriptyline and CYP2C19
DPWG	citalopram	Annotation of DPWG Guideline for citalopram and CYP2C19	yes	yes
DPWG	clomipramine	Annotation of DPWG Guideline for clomipramine and CYP2C19		yes
DPWG	clopidogrel	Annotation of DPWG Guideline for clopidogrel and CYP2C19	yes	yes
DPWG	doxepin	Annotation of DPWG Guideline for doxepin and CYP2C19
DPWG	escitalopram	Annotation of DPWG Guideline for escitalopram and CYP2C19	yes	yes
DPWG	esomeprazole	Annotation of DPWG Guideline for esomeprazole and CYP2C19
DPWG	fluvoxamine	Annotation of DPWG Guideline for fluvoxamine and CYP2C19
DPWG	imipramine	Annotation of DPWG Guideline for imipramine and CYP2C19	yes	yes
DPWG	lansoprazole	Annotation of DPWG Guideline for lansoprazole and CYP2C19	yes	yes
DPWG	mavacamten	Annotation of DPWG Guideline for mavacamten and CYP2C19	yes	yes
DPWG	mirtazapine	Annotation of DPWG Guideline for mirtazapine and CYP2C19
DPWG	moclobemide	Annotation of DPWG Guideline for moclobemide and CYP2C19
DPWG	omeprazole	Annotation of DPWG Guideline for omeprazole and CYP2C19	yes	yes
DPWG	pantoprazole	Annotation of DPWG Guideline for pantoprazole and CYP2C19	yes	yes
DPWG	prasugrel	Annotation of DPWG Guideline for prasugrel and CYP2C19
DPWG	rabeprazole	Annotation of DPWG Guideline for rabeprazole and CYP2C19
DPWG	sertraline	Annotation of DPWG Guideline for sertraline and CYP2C19	yes	yes

GtoPdb / IUPHAR curated pharmacology

(IUPHAR/BPS Guide to Pharmacology — expert-curated)

Target class: enzyme — CYP2 family: drug metabolising subset

Most potent curated ligand interactions (3 total), top 3:

Ligand	Action	Affinity	Parameter
compound 30 [PMID: 22239545]	Inhibition	7.7	pKi
compound 51 [Crosignani et al., 2011]	Inhibition	7.29	pIC50
UE2343	Inhibition	5.77	pIC50

Binding affinities (BindingDB)

131 measured of 352 human assays (353 total across all organisms); most potent 50 below. Values come from heterogeneous assays and are not directly comparable.

Ligand	Measure	Value	Patent
(6S)-6-(4-fluorophenyl)-3-[(1S)-1-[4-(4-fluorophenyl)phenyl]ethyl]-6-(2-hydroxyethyl)-1,3-oxazinan-2-one	IC50	0.51 nM	US-8598163: Derivatives of [1,3]Oxazin-2-one useful for the treatment of metabolic diseases such as lipid disorders
3-[(6R)-3-[(1S)-1-[4-(4-fluorophenyl)phenyl]ethyl]-2-oxo-6-phenyl-1,3-oxazinan-6-yl]propanamide	IC50	0.55 nM	US-8598163: Derivatives of [1,3]Oxazin-2-one useful for the treatment of metabolic diseases such as lipid disorders
(6R)-3-[(1S)-1-[4-(4-fluorophenyl)phenyl]ethyl]-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	0.55 nM	US-8598163: Derivatives of [1,3]Oxazin-2-one useful for the treatment of metabolic diseases such as lipid disorders
2,2-dimethyl-3-[(6R)-3-[(1S)-1-[4-(1-methyl-2-oxo-4-pyridinyl)phenyl]ethyl]-2-oxo-6-phenyl-1,3-oxazinan-6-yl]propanenitrile	IC50	0.61 nM	US-8575157
(6R)-6-(2,2-dimethylbut-3-ynyl)-3-[(1S)-1-[4-(6-oxo-1H-pyridin-3-yl)phenyl]ethyl]-6-phenyl-1,3-oxazinan-2-one	IC50	0.65 nM	US-8575157
3-[(6R)-6-(4-fluorophenyl)-3-[(1S)-1-[4-(1-methyl-6-oxo-3-pyridinyl)phenyl]ethyl]-2-oxo-1,3-oxazinan-6-yl]-2,2-dimethylpropanenitrile	IC50	0.72 nM	US-8575157
(6R)-3-[(1S)-1-[4-(2,4-difluorophenyl)phenyl]ethyl]-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	0.72 nM	US-8598163: Derivatives of [1,3]Oxazin-2-one useful for the treatment of metabolic diseases such as lipid disorders
(6S)-3-[(1S)-1-[4-(2,4-difluorophenyl)phenyl]ethyl]-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one	IC50	0.75 nM	US-8598163: Derivatives of [1,3]Oxazin-2-one useful for the treatment of metabolic diseases such as lipid disorders
(6S)-3-[(1S)-1-(4-bromophenyl)ethyl]-6-(4-fluorophenyl)-6-(2-hydroxy-2-methylpropyl)-1,3-oxazinan-2-one	IC50	0.76 nM	US-8598163: Derivatives of [1,3]Oxazin-2-one useful for the treatment of metabolic diseases such as lipid disorders
(6S)-3-[(1S)-1-(4-bromophenyl)ethyl]-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	0.79 nM	US-8598163: Derivatives of [1,3]Oxazin-2-one useful for the treatment of metabolic diseases such as lipid disorders
(6S)-3-[(1S)-1-[4-(1-ethyl-2-oxo-4-pyridinyl)phenyl]ethyl]-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	0.8 nM	US-8575157
(6S)-3-[(1S)-1-[4-[1-(cyclopropylmethyl)-6-oxopyridazin-3-yl]phenyl]ethyl]-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	0.86 nM	US-8592410: Cyclic inhibitors of 11BETA-hydroxysteroid dehydrogenase 1
(6R)-6-ethyl-3-[(1S)-1-[4-(1-methyl-2-oxo-4-pyridinyl)phenyl]propyl]-6-phenyl-1,3-oxazinan-2-one	IC50	0.87 nM	US-8575157
(6S)-6-(2-hydroxy-2-methylpropyl)-3-[(1S)-1-[4-(2-oxo-1-propan-2-yl-4-pyridinyl)phenyl]ethyl]-6-phenyl-1,3-oxazinan-2-one	IC50	0.96 nM	US-8575157
(2S)-N-[5-[2-(2-methoxy-3-pyridinyl)-7-methylimidazo[1,2-a]pyridin-3-yl]-6-[2-(1-methylisoquinolin-6-yl)ethynyl]-2-pyridinyl]-2-(methylamino)propanamide	IC50	1 nM	US-9481673: 6-alkynyl-pyridine derivatives
(2S)-2-(methylamino)-N-[6-[2-(1-methylisoquinolin-6-yl)ethynyl]-5-[7-methyl-2-(2-methyl-4-pyridinyl)imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]propanamide	IC50	1 nM	US-9481673: 6-alkynyl-pyridine derivatives
(2S)-2-(methylamino)-N-[6-[2-(1-methylisoquinolin-6-yl)ethynyl]-5-[7-methyl-2-(1-methylpyrazol-4-yl)imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]propanamide	IC50	1 nM	US-9481673: 6-alkynyl-pyridine derivatives
(2S)-2-(methylamino)-N-[6-[2-(1-methylisoquinolin-6-yl)ethynyl]-5-[7-methyl-2-(3-methylimidazol-4-yl)imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]propanamide	IC50	1 nM	US-9481673: 6-alkynyl-pyridine derivatives
(2S)-2-(methylamino)-N-[6-[2-(1-methylisoquinolin-6-yl)ethynyl]-5-[7-methyl-2-(6-methyl-3-pyridinyl)imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]propanamide	IC50	1 nM	US-9481673: 6-alkynyl-pyridine derivatives
(2S)-2-(methylamino)-N-[6-[2-(1-methylisoquinolin-6-yl)ethynyl]-5-[7-methyl-2-(2-methylpyrimidin-5-yl)imidazo[1,2-a]pyridin-3-yl]-2-pyridinyl]propanamide	IC50	1 nM	US-9481673: 6-alkynyl-pyridine derivatives
(2S)-N-[5-[2-(2-methoxy-4-pyridinyl)-7-methylimidazo[1,2-a]pyridin-3-yl]-6-[2-(1-methylisoquinolin-6-yl)ethynyl]-2-pyridinyl]-2-(methylamino)propanamide	IC50	1 nM	US-9481673: 6-alkynyl-pyridine derivatives
(2S)-N-[5-[2-(6-methoxy-3-pyridinyl)-7-methylimidazo[1,2-a]pyridin-3-yl]-6-[2-(1-methylisoquinolin-6-yl)ethynyl]-2-pyridinyl]-2-(methylamino)propanamide	IC50	1 nM	US-9481673: 6-alkynyl-pyridine derivatives
(2S)-N-[5-[2-(2-methoxy-3-pyridinyl)-7-methylimidazo[1,2-a]pyridin-3-yl]-6-[2-(1-methyl-2-oxoquinolin-6-yl)ethynyl]-2-pyridinyl]-2-(methylamino)propanamide	IC50	1 nM	US-9481673: 6-alkynyl-pyridine derivatives
(2S)-2-(methylamino)-N-[5-[7-methyl-2-(2-methyl-4-pyridinyl)imidazo[1,2-a]pyridin-3-yl]-6-(2-phenylethynyl)-2-pyridinyl]propanamide	IC50	1 nM	US-9481673: 6-alkynyl-pyridine derivatives
(2S)-N-[5-[2-(2-methoxy-4-pyridinyl)-7-methylimidazo[1,2-a]pyridin-3-yl]-6-[2-(1-methyl-2-oxoquinolin-6-yl)ethynyl]-2-pyridinyl]-2-(methylamino)propanamide	IC50	1 nM	US-9481673: 6-alkynyl-pyridine derivatives
(2S)-N-[5-[2-(6-methoxy-3-pyridinyl)-7-methylimidazo[1,2-a]pyridin-3-yl]-6-[2-(1-methyl-2-oxoquinolin-6-yl)ethynyl]-2-pyridinyl]-2-(methylamino)propanamide	IC50	1 nM	US-9481673: 6-alkynyl-pyridine derivatives
(6S)-3-[(1S)-1-[4-(1-ethyl-5-methyl-6-oxo-3-pyridinyl)phenyl]ethyl]-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	1.01 nM	US-8575157
2,2-dimethyl-3-[(6R)-3-[(1S)-1-[4-(1-methyl-6-oxo-3-pyridinyl)phenyl]ethyl]-2-oxo-6-phenyl-1,3-oxazinan-6-yl]propanenitrile	IC50	1.03 nM	US-8575157
(6S)-3-[(1S)-1-[4-(1-cyclopropyl-6-oxopyridazin-3-yl)phenyl]ethyl]-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	1.08 nM	US-8592410: Cyclic inhibitors of 11BETA-hydroxysteroid dehydrogenase 1
(6S)-3-[(1S)-1-[4-(4-fluorophenyl)phenyl]ethyl]-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	1.08 nM	US-8598163: Derivatives of [1,3]Oxazin-2-one useful for the treatment of metabolic diseases such as lipid disorders
2,2-dimethyl-3-[(6R)-2-oxo-3-[(1S)-1-[4-(2-oxo-1H-pyridin-4-yl)phenyl]ethyl]-6-phenyl-1,3-oxazinan-6-yl]propanenitrile	IC50	1.11 nM	US-8575157
(6S)-6-(2-hydroxy-2-methylpropyl)-3-[(1S)-1-[4-[6-oxo-1-(2,2,2-trifluoroethyl)pyridazin-3-yl]phenyl]ethyl]-6-phenyl-1,3-oxazinan-2-one	IC50	1.14 nM	US-8592410: Cyclic inhibitors of 11BETA-hydroxysteroid dehydrogenase 1
(6S)-3-[(1S)-1-[4-(1-cyclopropyl-2-oxo-4-pyridinyl)phenyl]ethyl]-6-(2-fluorophenyl)-6-(2-hydroxy-2-methylpropyl)-1,3-oxazinan-2-one	IC50	1.2 nM	US-8575157
(6S)-3-[(1S)-1-[4-(1,5-dimethyl-6-oxopyridazin-3-yl)phenyl]ethyl]-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	1.25 nM	US-8592410: Cyclic inhibitors of 11BETA-hydroxysteroid dehydrogenase 1
(6S)-3-[(1S)-1-[4-[1-(difluoromethyl)-2-oxo-4-pyridinyl]phenyl]ethyl]-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	1.25 nM	US-8575157
(6S)-3-[(1S)-1-[4-(difluoromethoxy)phenyl]ethyl]-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one	IC50	1.3 nM	US-8598163: Derivatives of [1,3]Oxazin-2-one useful for the treatment of metabolic diseases such as lipid disorders
(6S)-3-[(1S)-1-[4-(1-ethyl-6-oxo-3-pyridinyl)phenyl]ethyl]-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	1.35 nM	US-8575157
(6S)-6-(4-fluorophenyl)-6-(2-hydroxy-2-methylpropyl)-3-[(1S)-1-[4-(1-methyl-6-oxopyridazin-3-yl)phenyl]ethyl]-1,3-oxazinan-2-one	IC50	1.39 nM	US-8592410: Cyclic inhibitors of 11BETA-hydroxysteroid dehydrogenase 1
(6S)-3-[(1S)-1-[4-(1,5-dimethyl-6-oxo-3-pyridinyl)phenyl]ethyl]-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	1.4 nM	US-8575157
(6S)-3-[(1S)-1-[4-(1-cyclopropyl-2-oxo-4-pyridinyl)phenyl]ethyl]-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	1.4 nM	US-8575157
(6R)-6-(3-hydroxypropyl)-3-[(1S)-1-[4-(1-methyl-6-oxo-3-pyridinyl)phenyl]ethyl]-6-phenyl-1,3-oxazinan-2-one	IC50	1.44 nM	US-8575157
(6S)-6-(2-hydroxy-2-methylpropyl)-3-[(1S)-1-[4-[2-oxo-1-(2,2,2-trifluoroethyl)-4-pyridinyl]phenyl]ethyl]-6-phenyl-1,3-oxazinan-2-one	IC50	1.47 nM	US-8575157
(6S)-3-[(1S)-1-[4-(2,4-difluorophenyl)phenyl]ethyl]-6-(4-fluorophenyl)-6-(2-hydroxy-2-methylpropyl)-1,3-oxazinan-2-one	IC50	1.48 nM	US-8598163: Derivatives of [1,3]Oxazin-2-one useful for the treatment of metabolic diseases such as lipid disorders
(6S)-6-(2-fluorophenyl)-6-(2-hydroxy-2-methylpropyl)-3-[(1S)-1-[4-(1-methyl-2-oxo-4-pyridinyl)phenyl]ethyl]-1,3-oxazinan-2-one	IC50	1.49 nM	US-8575157
(6S)-3-[(1S)-1-[4-(1-ethyl-6-oxopyridazin-3-yl)phenyl]ethyl]-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	1.52 nM	US-8592410: Cyclic inhibitors of 11BETA-hydroxysteroid dehydrogenase 1
(6S)-6-(2-hydroxy-2-methylpropyl)-3-[(1S)-1-[4-(6-oxo-1-propan-2-yl-3-pyridinyl)phenyl]ethyl]-6-phenyl-1,3-oxazinan-2-one	IC50	1.53 nM	US-8575157
(S)-(4-fluorophenyl)-[4-[(5-methylpyrazolidin-3-yl)amino]quinazolin-2-yl]methanol	IC50	1.55 nM	US-9295672: Optically active pyrazolylaminoquinazoline, and pharmaceutical compositions and methods of use thereof
(6S)-3-[(1S)-1-[4-(1-cyclopropyl-6-oxo-3-pyridinyl)phenyl]ethyl]-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	1.59 nM	US-8575157
(6S)-6-(2-hydroxy-2-methylpropyl)-3-[(1S)-1-[4-(1-methyl-2-oxo-4-pyridinyl)phenyl]ethyl]-6-phenyl-1,3-oxazinan-2-one	IC50	1.62 nM	US-8575157
(6S)-3-[(1S)-1-[4-(1,2-dimethyl-6-oxo-4-pyridinyl)phenyl]ethyl]-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one	IC50	1.64 nM	US-8575157

ChEMBL bioactivities

6100 potent at pChembl≥5 of 6100 total, top 50 by pChembl (potency: 10 = 0.1 nM, 6 = 1 µM).

pChembl	Type	Value	Unit	Molecule
10.70	IC50	0.02	nM	MICONAZOLE
9.00	Potency	1	nM	CHEMBL1402106
9.00	Potency	1	nM	CHEMBL1552243
9.00	Potency	1	nM	CHEMBL1371957
9.00	Potency	1	nM	CHEMBL1565567
9.00	Potency	1	nM	CHEMBL1338347
9.00	Potency	1	nM	CHEMBL1534735
9.00	Potency	1	nM	CHEMBL1328802
9.00	Potency	1	nM	CHEMBL1370938
9.00	Potency	1	nM	CHEMBL479014
8.89	Potency	1.3	nM	CIRAZOLINE
8.85	AC50	1.413	nM	CHEMBL1340517
8.70	Potency	2	nM	CHEMBL1371217
8.70	Potency	2	nM	CHEMBL1515310
8.70	Potency	2	nM	CHEMBL1374426
8.70	Potency	2	nM	CHEMBL1489668
8.70	Potency	2	nM	CHEMBL1611974
8.70	AC50	1.995	nM	CHEMBL1374426
8.60	Potency	2.5	nM	PENTETIC ACID
8.60	Potency	2.5	nM	CHEMBL1530445
8.60	Potency	2.5	nM	CHEMBL1532768
8.60	Potency	2.5	nM	CIS-RESVERATROL
8.60	Potency	2.5	nM	CHEMBL1317950
8.60	Potency	2.5	nM	CHEMBL1514398
8.60	Potency	2.5	nM	CHEMBL1256392
8.60	Potency	2.5	nM	ARCTIGENIN
8.60	AC50	2.512	nM	PENTETIC ACID
8.60	AC50	2.512	nM	CIS-RESVERATROL
8.60	AC50	2.512	nM	CHEMBL1514398
8.60	AC50	2.512	nM	CHEMBL1530445
8.60	AC50	2.512	nM	CHEMBL1317950
8.60	AC50	2.512	nM	ARCTIGENIN
8.60	AC50	2.512	nM	CHEMBL1256392
8.50	AC50	3.162	nM	CHEMBL1437054
8.50	AC50	3.162	nM	CHEMBL1355644
8.49	Potency	3.2	nM	CHEMBL1474703
8.49	Potency	3.2	nM	CHEMBL1355644
8.49	Potency	3.2	nM	CHEMBL1437054
8.45	AC50	3.548	nM	CHEMBL1541405
8.40	Potency	4	nM	CHEMBL1525438
8.40	Potency	4	nM	CHEMBL1486692
8.40	Potency	4	nM	CHEMBL1397334
8.40	Potency	4	nM	CHEMBL1179104
8.40	AC50	3.981	nM	CHEMBL1397334
8.40	AC50	3.981	nM	CHEMBL1179104
8.34	IC50	4.6	nM	CHEMBL4593464
8.30	Potency	5	nM	CHEMBL1487450
8.30	Potency	5	nM	CHEMBL1329968
8.30	AC50	5.012	nM	CHEMBL1329968
8.30	AC50	5.012	nM	CHEMBL1477447

PubChem BioAssay actives

814 with measured affinity, of 6100 total; 50 most potent distinct compounds. Largely complementary to BindingDB; screening values are coarse (µM, 4 dp), so sub-nM hits tie at the floor.

Compound	Assay	Type	Value	Unit
Miconazole	1849445: Inhibition of CYP2C19 in human liver Microsome using omeprazole as substrate in presence of NADPH by LC-MS/MS analysis	ic50	<0.0001	uM
(1R,2S,5S,8R,9R,10S,11R,18R)-10,18-dihydroxy-12,12-dimethyl-6-methylidene-9-(1,3-thiazol-5-ylmethoxy)-17-oxapentacyclo[7.6.2.15,8.01,11.02,8]octadec-14-en-7-one	2072305: Inhibition of CYP2C19 (unknown origin) using S-mephenytoin as substrate preincubated for 5 min followed by NADPH addition and measured after 30 mins	ic50	0.0051	uM
1-(4-butoxyphenyl)imidazole	54057: Inhibition of cytochrome P450 CYP2C19	ic50	0.0070	uM
5-[2-(4-tert-butylphenyl)sulfanylethyl]-1H-imidazole	479284: Inhibition of human CYP2C19 expressed in insect cell microsome after 30 mins by fluorescence assay	ic50	0.0085	uM
(10bS)-7-acetyl-8,10-dihydroxy-3,9,10b-trimethyl-2H-[1]benzofuro[2,3-g]indazol-4-one	1922615: Inhibition of CYP2C19 in human liver microsomes	ic50	0.0090	uM
2-[2-(4-tert-butylphenyl)sulfanyl-1-(1H-imidazol-5-yl)ethyl]pyridine	512106: Inhibition of CYP2C19	ic50	0.0100	uM
6-methyl-2-(pyridin-2-ylmethylsulfanyl)-1H-benzimidazole	656024: Inhibition of recombinant CYP2C19 using 3-O-methylfluorescein as substrate preincubated for 3 mins	ki	0.0200	uM
4-[[2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one	254934: Concentration required to inhibit cytochrome P450 isozyme CYP2C19 in vitro by 50%	ic50	0.0260	uM
2-[5-[7-chloro-8-[1-(2-fluorophenyl)ethylamino]-1,5-naphthyridin-2-yl]pyrimidin-2-yl]propan-2-ol	1693257: Inhibition of recombinant CYP2C19 (unknown origin)	ic50	0.0300	uM
2-[5-[3-chloro-4-(2,5-dimethylanilino)quinolin-6-yl]pyrimidin-2-yl]propan-2-ol	1693257: Inhibition of recombinant CYP2C19 (unknown origin)	ic50	0.0300	uM
N-[4-[(1-cycloheptylpyrazolo[3,4-d]pyrimidin-6-yl)amino]phenyl]-N-(2-morpholin-4-ylethyl)methanesulfonamide	617436: Inhibition of CYP2C19	ic50	0.0300	uM
(2-ethyl-1-benzofuran-3-yl)-(4-hydroxy-3,5-dimethylphenyl)methanone	282441: Inhibition of human CYP2C19	ki	0.0330	uM
2-chloro-4-[(2-chlorophenyl)methyl-[1-(4-methyl-1,2,4-triazol-3-yl)ethyl]amino]benzonitrile	424664: Inhibition of CYP2C19	ic50	0.0330	uM
2-chloro-4-[(2-chlorophenyl)methyl-[1-(2-methylpyrazol-3-yl)ethyl]amino]benzonitrile	424664: Inhibition of CYP2C19	ic50	0.0330	uM
2-chloro-4-[(2-chlorophenyl)methyl-[1-(1-methylimidazol-2-yl)ethyl]amino]benzonitrile	424664: Inhibition of CYP2C19	ic50	0.0330	uM
2-chloro-4-[(2-chlorophenyl)methyl-[1-(3-methyl-1,2-oxazol-5-yl)ethyl]amino]benzonitrile	424664: Inhibition of CYP2C19	ic50	0.0330	uM
2-chloro-4-[(2-chlorophenyl)methyl-[1-(1-ethyltetrazol-5-yl)ethyl]amino]benzonitrile	424664: Inhibition of CYP2C19	ic50	0.0330	uM
2-chloro-4-[(2-chlorophenyl)methyl-[1-(1-methyltetrazol-5-yl)ethyl]amino]benzonitrile	424664: Inhibition of CYP2C19	ic50	0.0330	uM
2-chloro-4-[(2-chlorophenyl)methyl-[1-(1-methyltetrazol-5-yl)propyl]amino]benzonitrile	424664: Inhibition of CYP2C19	ic50	0.0330	uM
8-imidazol-1-yl-5,6,7,8-tetrahydroquinoline	2022035: Inhibition of CYP450 (unknown origin)	ic50	0.0335	uM
N-[3-fluoro-5-(2H-tetrazol-5-yl)phenyl]-N-[[4-(trifluoromethyl)phenyl]methyl]propanamide	664816: Inhibition of human recombinant CYP2C19 incubated for 15 mins prior to substrate addition measured after 30 mins by spectrophotometry	ic50	0.0380	uM
3-[[(1R,2S,5S,8R,9S,10S,11R,18R)-10,18-dihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.15,8.01,11.02,8]octadec-14-en-9-yl]oxy]propanoic acid	2072305: Inhibition of CYP2C19 (unknown origin) using S-mephenytoin as substrate preincubated for 5 min followed by NADPH addition and measured after 30 mins	ic50	0.0387	uM
4-[[(2S)-1-hydroxy-3-phenylpropan-2-yl]amino]-3-(6-imidazol-1-yl-4-methyl-1H-benzimidazol-2-yl)-1H-pyridin-2-one	290573: Inhibition of CYP2C19 in microsomes	ic50	0.0400	uM
Fluoxetine	1254876: Inhibition of CYP2C19 (unknown origin) using luciferin tagged substrate preincubated for 10 mins before substrate addition	ic50	0.0400	uM
2-chloro-4-[(2-chlorophenyl)methyl-[1-(1-methyltriazol-4-yl)ethyl]amino]benzonitrile	424664: Inhibition of CYP2C19	ic50	0.0400	uM
6-methoxy-2-[(4-propan-2-ylphenyl)methylsulfanyl]-1H-benzimidazole	656024: Inhibition of recombinant CYP2C19 using 3-O-methylfluorescein as substrate preincubated for 3 mins	ki	0.0400	uM
2-[(4-iodophenyl)methylsulfanyl]-6-methoxy-1H-benzimidazole	656024: Inhibition of recombinant CYP2C19 using 3-O-methylfluorescein as substrate preincubated for 3 mins	ki	0.0400	uM
N-[(1R)-1-[1-ethyl-6-(trifluoromethyl)benzimidazol-2-yl]ethyl]pyridine-4-sulfonamide	1241582: Inhibition of CYP2C19 in human liver microsomes incubated for 5 mins in presence of NADPH and specific substrates by LC/MS/MS method	ic50	0.0400	uM
5-(4-butoxyphenyl)-1,3-oxazole	54057: Inhibition of cytochrome P450 CYP2C19	ic50	0.0460	uM
4-(4-butoxyphenyl)pyridine	54057: Inhibition of cytochrome P450 CYP2C19	ic50	0.0460	uM
1-(4-butoxyphenyl)-5-methylimidazole	54057: Inhibition of cytochrome P450 CYP2C19	ic50	0.0460	uM
5-(4-butoxyphenyl)-1,2-thiazole	54057: Inhibition of cytochrome P450 CYP2C19	ic50	0.0460	uM
2-[3-(4-imidazol-1-ylphenoxy)propyl]pyridine	54376: Inhibition of cytochrome P450 2C19	ic50	0.0460	uM
4-[3-(4-imidazol-1-ylphenoxy)propyl]pyridine	54376: Inhibition of cytochrome P450 2C19	ic50	0.0460	uM
3-[3-(4-imidazol-1-ylphenoxy)propyl]pyridine	54376: Inhibition of cytochrome P450 2C19	ic50	0.0460	uM
2-[(4-imidazol-1-ylphenoxy)methyl]pyridine	54376: Inhibition of cytochrome P450 2C19	ic50	0.0460	uM
2-hexoxy-5-imidazol-1-ylpyridine	54376: Inhibition of cytochrome P450 2C19	ic50	0.0460	uM
1-[[4-(hydroxycarbamoyl)phenyl]methyl]-3,4-dihydro-2H-quinoline-6-carboxamide	1764824: Inhibition of CYP2C19 (unknown origin)	ic50	0.0470	uM
2-(4-chloro-N-[4-(3-hydroxypropyl)phenyl]sulfonylanilino)-N-[(2-hydroxy-1H-indol-3-yl)imino]acetamide	257228: Inhibitory activity against cytochrome P450 2C19 isoform	ic50	0.0500	uM
2-heptylsulfanyl-6-methoxy-1H-benzimidazole	656024: Inhibition of recombinant CYP2C19 using 3-O-methylfluorescein as substrate preincubated for 3 mins	ki	0.0500	uM
6-methoxy-2-[(3-phenoxyphenyl)methylsulfanyl]-1H-benzimidazole	656024: Inhibition of recombinant CYP2C19 using 3-O-methylfluorescein as substrate preincubated for 3 mins	ki	0.0500	uM
N-[3-fluoro-5-(2H-tetrazol-5-yl)phenyl]-N-[[4-(trifluoromethoxy)phenyl]methyl]propanamide	664816: Inhibition of human recombinant CYP2C19 incubated for 15 mins prior to substrate addition measured after 30 mins by spectrophotometry	ic50	0.0510	uM
4-[1-(1H-imidazol-5-yl)-2-[4-(trifluoromethyl)phenyl]sulfanylethyl]pyridine	512106: Inhibition of CYP2C19	ic50	0.0550	uM
6-methoxy-2-(naphthalen-2-ylmethylsulfanyl)-1H-benzimidazole	656024: Inhibition of recombinant CYP2C19 using 3-O-methylfluorescein as substrate preincubated for 3 mins	ki	0.0600	uM
6-methoxy-2-(2-methylpropylsulfanyl)-1H-benzimidazole	656024: Inhibition of recombinant CYP2C19 using 3-O-methylfluorescein as substrate preincubated for 3 mins	ki	0.0600	uM
6-methoxy-2-pentylsulfanyl-1H-benzimidazole	656024: Inhibition of recombinant CYP2C19 using 3-O-methylfluorescein as substrate preincubated for 3 mins	ki	0.0600	uM
N-(diaminomethylidene)-4-[1-(pyridine-4-carbonyl)piperidin-4-yl]-3-(trifluoromethyl)benzamide	701658: Inhibition of CYP2C19 in human liver microsomes using 7-ethoxy-3-cyanocoumarin as substrate after 45 mins by LC/MS/MS analysis	ic50	0.0600	uM
(1R,2R,3R)-N-hydroxy-2-[4-(1,3-oxazol-5-yl)phenyl]-3-phenylcyclopropane-1-carboxamide	1065605: Inhibition of human CYP2C19	ic50	0.0600	uM
2-chloro-4-[(2-chlorophenyl)methyl-[2-methyl-1-(4-methyl-1,2,4-triazol-3-yl)propyl]amino]benzonitrile	424664: Inhibition of CYP2C19	ic50	0.0630	uM
2-chloro-4-[(2-chlorophenyl)methyl-[1-(2-methyl-1,3-thiazol-4-yl)ethyl]amino]benzonitrile	424664: Inhibition of CYP2C19	ic50	0.0670	uM

CTD chemical–gene interactions

386 total (human), top 30 by PubMed support.

Chemical	Actions (top 5)	PubMed papers
Mephenytoin	decreases reaction, increases oxidation, increases hydroxylation, increases chemical synthesis, decreases activity (+4 more)	36
Omeprazole	decreases methylation, decreases reaction, increases chemical synthesis, increases oxidation, decreases chemical synthesis (+6 more)	25
Clopidogrel	increases cleavage, decreases reaction, affects phosphorylation, affects abundance, increases oxidation (+10 more)	22
Lansoprazole	affects reaction, affects response to substance, decreases metabolic processing, affects metabolic processing, increases hydroxylation (+4 more)	14
Rifampin	increases activity, increases expression	10
Ticlopidine	affects cotreatment, decreases activity, decreases reaction, increases hydroxylation, increases metabolic processing (+2 more)	10
Phenytoin	affects response to substance, decreases hydroxylation, decreases metabolic processing, affects metabolic processing, increases hydroxylation (+2 more)	9
Chlorpyrifos	increases metabolic processing, decreases expression, increases expression, affects metabolic processing, decreases activity	8
4-hydroxymephenytoin	increases chemical synthesis, increases hydroxylation, increases metabolic processing, decreases reaction	7
Phenobarbital	increases metabolic processing, affects expression, increases activity, increases expression, decreases metabolic processing	7
Troglitazone	increases response to substance, increases metabolic processing, decreases activity, increases expression, affects cotreatment (+1 more)	6
Methoxychlor	decreases methylation, increases hydroxylation, affects cotreatment	6
Diclofenac	increases response to substance, decreases reaction, affects cotreatment, affects response to substance, increases hydroxylation	5
Fluoxetine	increases chemical synthesis, increases hydroxylation, decreases activity, affects metabolic processing, increases metabolic processing (+1 more)	5
Tranylcypromine	affects cotreatment, affects reaction, increases metabolic processing, decreases reaction, increases chemical synthesis (+1 more)	5
Fluconazole	decreases metabolic processing, increases metabolic processing, decreases activity	5
Aflatoxin B1	decreases expression, decreases methylation, affects cotreatment, affects response to substance, affects expression	5
perfluorooctane sulfonic acid	decreases activity, decreases expression, increases expression, decreases reaction, increases oxidation	4
N-3-benzylnirvanol	decreases reaction, increases oxidation, decreases activity	4
Pantoprazole	decreases activity, affects response to substance, increases metabolic processing, decreases reaction, increases hydroxylation	4
Chlorpromazine	decreases activity, affects cotreatment, affects response to substance, affects methylation, decreases response to substance	4
Clozapine	increases chemical synthesis, increases metabolic processing, increases abundance, affects cotreatment, affects response to substance (+1 more)	4
Cyclophosphamide	affects activity, affects response to substance, increases hydroxylation, increases chemical synthesis, increases metabolic processing (+3 more)	4
NADP	increases metabolic processing, affects reaction, decreases reaction, affects cotreatment, decreases activity	4
Warfarin	affects response to substance, affects reaction, affects metabolic processing	4
Arachidonic Acid	increases abundance, decreases activity, affects cotreatment, affects response to substance, decreases reaction (+2 more)	4
bisphenol A	decreases activity, decreases methylation, increases glutathionylation, increases hydroxylation	3
perfluorooctanoic acid	decreases activity, decreases expression, increases expression	3
clozapine N-oxide	decreases reaction, increases chemical synthesis, increases metabolic processing, increases abundance	3
Adenosine Diphosphate	increases expression, affects cotreatment, affects response to substance, affects reaction	3

ChEMBL screening assays

2771 unique, capped per target: 2719 admet, 51 binding, 1 functional

Representative assays (with source publication via chembl_document):

Assay ID	Type	Description	Source paper
CHEMBL1000511	ADMET	Inhibition of human recombinant CYP2C19 expressed in insect microsomes	Discovery of (R)-4-(8-fluoro-2-oxo-1,2-dihydroquinazolin-3(4H)-yl)-N-(3-(7-methyl-1H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl)piperidine-1-carboxamide (BMS-694153): a potent antagonist of the human calcitonin gene-related peptide receptor for migraine with rapid and efficient intranasal exposure. — J Med Chem
CHEMBL1678713	Binding	Inhibition of CYP2C19 in human liver microsome	Conformationally constrained farnesoid X receptor (FXR) agonists: heteroaryl replacements of the naphthalene. — Bioorg Med Chem Lett
CHEMBL1741323	Functional	PUBCHEM_BIOASSAY: Cytochrome panel assay with activity outcomes. (Class of assay: other) Panel member name: p450-cyp2c19 Compounds with AC50 equal or less than 10 uM are considered active	PubChem BioAssay data set

Cellosaurus cell lines

33 cell lines: 29 transformed cell line, 3 induced pluripotent stem cell, 1 cancer cell line

First 10 cell lines (id-ordered, not curated):

Cellosaurus	Name	Category	Sex
CVCL_5E78	GM12840	Transformed cell line	Male
CVCL_7274	GM00130	Transformed cell line	Male
CVCL_7465	GM07348	Transformed cell line	Female
CVCL_7508	GM11829	Transformed cell line	Male
CVCL_7521	GM12145	Transformed cell line	Female
CVCL_7525	GM12751	Transformed cell line	Female
CVCL_7526	GM12878	Transformed cell line	Female
CVCL_9595	GM07357	Transformed cell line	Male
CVCL_9613	GM12248	Transformed cell line	Male
CVCL_9614	GM12249	Transformed cell line	Female

Clinical trials (associated diseases)

300 trials via MONDO — disease-level, not drug-specific.

Trial	Phase	Status	Title
NCT00077818	PHASE4	COMPLETED	Enoxaparin Versus Unfractionated Heparin in Subjects Who Present to the Emergency Department With Acute Coronary Syndrome (RESCUE)
NCT00206817	PHASE4	WITHDRAWN	Rapid Assessment of Cardiac Markers for the Evaluation of Acute Coronary Syndrome (RACE-ACS)
NCT00351364	PHASE4	TERMINATED	Does Montelukast Have an Affect on the Function of the Artery in Patients With Heart Disease
NCT00404053	PHASE4	COMPLETED	Clopidogrel Maintaining Dosage in Acute Coronary Syndrome After Drug Eluting Stent Implantation
NCT00404716	PHASE4	COMPLETED	Triple Versus Dual Antiplatelet Therapy in Patients Undergoing Coronary Stent Implantation
NCT00404781	PHASE4	COMPLETED	Effects of Optimized Antiplatelet Treatment After Percutaneous Coronary Intervention
NCT00405717	PHASE4	COMPLETED	Effects of Atorvastatin Versus Pravastatin on Platelet Inhibition by Clopidogrel
NCT00412802	PHASE4	COMPLETED	Adaptation Dose of Enoxaparin in Moderate Renal Failure Patients With Acute Coronary Syndrome
NCT00452517	PHASE4	COMPLETED	Comparison of Stent Graft, Sirolimus Stent, and Bare Metal Stent Implanted in Patients With Acute Coronary Syndrome
NCT00494247	PHASE4	COMPLETED	Endothelial Progenitor Cells-capture Stents in Acute Coronary Syndromes
NCT00627809	PHASE4	COMPLETED	Effect of Adjunctive Intracoronary Streptokinase on Late Term Left Ventricular Infarct Size and Volumes in Patients With Acute Myocardial Infarction
NCT00665834	PHASE4	COMPLETED	Comparison of Rosuvastatin and Atorvastatin in Patients With Acute Coronary Syndrome
NCT00683111	PHASE4	COMPLETED	Prevention of Gastrointestinal Bleeding in Patients With Severe Ischemic Heart Disease
NCT00700037	PHASE4	COMPLETED	Change in Plaque Characteristics With Atorvastatin
NCT00702936	PHASE4	UNKNOWN	Telmisartan Versus Ramipril After Acute Coronary Syndrome
NCT00718406	PHASE4	COMPLETED	Pain Relief of Metoprolol Versus Metoprolol Plus Morphine in Acute Chest Pain
NCT00728988	PHASE4	COMPLETED	Atorvastatin Pre-Treatment Study In Asian Patients With Acute Coronary Syndrome
NCT00736229	PHASE4	COMPLETED	Intravenous Exenatide in Coronary Intensive Care Unit (ICU) Patients
NCT00766896	PHASE4	COMPLETED	Platelet Hyperreactivity to Aspirin and Stroke
NCT00790387	PHASE4	COMPLETED	Tirofiban and Enoxaparin in High Risk Coronary Intervention
NCT00790907	PHASE4	COMPLETED	Fondaparinux Trial With Unfractionated Heparin (UFH) During Revascularization in Acute Coronary Syndromes (ACS)
NCT00815100	PHASE4	COMPLETED	Effects of the Ivabradine on Reduction of Inflammatory Markers in Patients With Acute Coronary Syndrome
NCT00822679	PHASE4	COMPLETED	Eszopiclone and Inflammatory Mediators in Patients With Acute Coronary Syndrome
NCT00827411	PHASE4	COMPLETED	Double Randomization of a Monitoring Adjusted Antiplatelet Treatment Versus a Common Antiplatelet Treatment for DES Implantation, and Interruption Versus Continuation of Double Antiplatelet Therapy
NCT00829660	PHASE4	COMPLETED	Acarbose Cardiovascular Evaluation Trial
NCT00914420	PHASE4	UNKNOWN	Optical Coherence Tomography (OCT) Evaluation of Re-endothelization: A Comparison of the Intrepide™ Stent Versus Taxus™
NCT00929279	PHASE4	COMPLETED	Efficacy of Abciximab Bolus Only Regimen in Providing Inhibition of Platelet Action Over Time
NCT00997750	PHASE4	COMPLETED	Efficacy and Safety of Lornoxicam in Patients With Acute Coronary Syndrome
NCT01040936	PHASE4	UNKNOWN	Intensive Lipid Lowering Treatment in Non-ST-elevation Acute Coronary Syndrome (NSTE-ACS) Patients
NCT01062516	PHASE4	COMPLETED	Influence of Esomeprazole on Antiplatelet Action of Clopidogrel Associated With Aspirin
NCT01068119	PHASE4	TERMINATED	Same-Day Discharge After Coronary Percutaneous Transluminal Coronary Angioplasty (PTCA)
NCT01094457	PHASE4	COMPLETED	Effects of Intensive Antiplatelet Therapy for Patients With Clopidogrel Resistance After Coronary Stent Implantation
NCT01099592	PHASE4	TERMINATED	Antidepressants to Promote Recovery of Cardiac Patients Suffering From Depression
NCT01115842	PHASE4	UNKNOWN	Vitamin D and Inflammatory Cytokine Levels After Acute Myocardial Infraction (MI)
NCT01135667	PHASE4	COMPLETED	Prasugrel Versus Double Dose Clopidogrel to Treat Clopidogrel Low-responsiveness After PCI
NCT01151176	PHASE4	SUSPENDED	Feasible Insulin Algorithm for Glycemic Control in Patients With Acute Coronary Syndrome
NCT01170338	PHASE4	UNKNOWN	Safety and Efficacy of the Novel Selective Nicotinic Receptor Partial Agonist, CHANTIX (Varenicline) in Patients With Acute Coronary Syndrome
NCT01171911	PHASE4	UNKNOWN	Comparison of Intravenous Injection of Calcium Antagonist and Beta-blockade on Endothelial Shear Stress of Coronary Artery
NCT01185938	PHASE4	COMPLETED	Statin Contrast Induced Nephropathy Prevention
NCT01201070	PHASE4	UNKNOWN	Study of Administration Of Antithrombin in Patients With Low Plasmatic Levels of Antithrombin After Cardiac Surgery