Imiglitazar

Summary

Imiglitazar (CHEMBL592054) is a phase-3 clinical-stage small molecule targeting PPARA; indicated across 1 condition including diabetes mellitus.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• Targets: 1 (PPARA)
• Indications: 1 condition
• Clinical trials: 6
• Chemistry: 470.5 Da · C28H26N2O5

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL592054
Name	Imiglitazar
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	9890879
Molecular formula	C28H26N2O5
Molecular weight	470.5
InChIKey	ULVDFHLHKNJICZ-QCWLDUFUSA-N

SMILES: CC1=C(N=C(O1)C2=CC=CC=C2)COC3=CC=C(C=C3)CO/N=C(\CCC(=O)O)/C4=CC=CC=C4

IUPAC name: (4E)-4-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl]methoxyimino]-4-phenylbutanoic acid

Also known as: Imiglitazar, Tak-559, TAK-559, imiglitazar, IMIGLITAZAR

Patent coverage: 131 distinct patent families (356 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
PPARA	Peroxisome proliferator-activated receptor-α	Agonist	7.17	0.7%	Q07869

Broader ChEMBL bioactivity targets: 2 (assay-derived). Sample: Peroxisome proliferator-activated receptor gamma, Peroxisome proliferator-activated receptor alpha.

Bioactivity

ChEMBL activities: 4 potent at pChembl ≥ 5 of 4 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
PPARG	8.4	EC50	4	nM	CHEMBL_ACT_2503980
PPARG	8.4	EC50	4	nM	CHEMBL_ACT_3091722
PPARA	8.3	EC50	5	nM	CHEMBL_ACT_3113056
PPARA	8.1	EC50	8	nM	CHEMBL_ACT_2503971

Target pathways

Aggregated over 1 target gene(s): PPARA.

Top Reactome pathways

13 total, by targets touching each:

Pathway	Targets	Genes
BMAL1:CLOCK,NPAS2 activates circadian expression	1	PPARA
PPARA activates gene expression	1	PPARA
Transcriptional activation of mitochondrial biogenesis	1	PPARA
Activation of gene expression by SREBF (SREBP)	1	PPARA
Transcriptional regulation of white adipocyte differentiation	1	PPARA
Nuclear Receptor transcription pathway	1	PPARA
Regulation of lipid metabolism by PPARalpha	1	PPARA
SUMOylation of intracellular receptors	1	PPARA
Cytoprotection by HMOX1	1	PPARA
Heme signaling	1	PPARA
Transcriptional regulation of brown and beige adipocyte differentiation by EBF2	1	PPARA
Expression of BMAL (ARNTL), CLOCK, and NPAS2	1	PPARA
RORA,B,C and NR1D1 (REV-ERBA) regulate gene expression	1	PPARA

Dominant GO biological processes

GO term	Targets
negative regulation of transcription by RNA polymerase II	1
response to hypoxia	1
gluconeogenesis	1
fatty acid metabolic process	1
heart development	1
response to nutrient	1
lactation	1
epidermis development	1
cellular response to starvation	1
hormone-mediated signaling pathway	1
gene expression	1
regulation of ketone metabolic process	1
negative regulation of macrophage derived foam cell differentiation	1
negative regulation of cholesterol storage	1
protein ubiquitination	1

Indications & clinical

Indications

1 indication (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
diabetes mellitus	3	MONDO:0005015	EFO:0000400

Clinical trials

Total trials: 6.

Phase distribution

Phase	Trials
PHASE3	6

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00759720	PHASE3	TERMINATED	Efficacy and Safety of TAK-559 Combined With Glyburide in Treating Subjects With Type 2 Diabetes Mellitus.
NCT00762112	PHASE3	TERMINATED	Safety Study of TAK-559 in Treating Subjects With Type 2 Diabetes Mellitus
NCT00762190	PHASE3	TERMINATED	Study of TAK-559 in Treating Subjects With Type 2 Diabetes Mellitus
NCT00762684	PHASE3	TERMINATED	Efficacy and Safety Study of TAK-559 in Treating Subjects With Type 2 Diabetes Mellitus
NCT00762957	PHASE3	TERMINATED	Safety and Efficacy of TAK-559 in Combination With Metformin in Patients With Type 2 Diabetes Mellitus.
NCT00763022	PHASE3	COMPLETED	Efficacy of TAK-559 in Treating Subjects With Type 2 Diabetes Mellitus

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

37 molecules share ≥1 primary target. Top 37 by shared-target count:

Molecule	Source	Status	Shared targets
SELADELPAR	ChEMBL + PubChem	Phase 4 (approved)	PPARA
BERBERINE	ChEMBL	Phase 4 (approved)	PPARA
CIPROFIBRATE	ChEMBL	Phase 4 (approved)	PPARA
CLOFIBRATE	ChEMBL	Phase 4 (approved)	PPARA
CYCLOSPORINE	ChEMBL	Phase 4 (approved)	PPARA
ELAFIBRANOR	ChEMBL	Phase 4 (approved)	PPARA
FENOFIBRATE	ChEMBL	Phase 4 (approved)	PPARA
FENOFIBRIC ACID	ChEMBL	Phase 4 (approved)	PPARA
GEMFIBROZIL	ChEMBL	Phase 4 (approved)	PPARA
PEMAFIBRATE	ChEMBL	Phase 4 (approved)	PPARA
PIOGLITAZONE	ChEMBL	Phase 4 (approved)	PPARA
RACECADOTRIL	ChEMBL	Phase 4 (approved)	PPARA
ROSIGLITAZONE	ChEMBL	Phase 4 (approved)	PPARA
ALEGLITAZAR	ChEMBL	Phase 3	PPARA
BEZAFIBRATE	ChEMBL	Phase 3	PPARA
GAMOLENIC ACID	ChEMBL	Phase 3	PPARA
ICOSAPENT	ChEMBL	Phase 3	PPARA
LANIFIBRANOR	ChEMBL	Phase 3	PPARA
LOBEGLITAZONE	ChEMBL	Phase 3	PPARA
MURAGLITAZAR	ChEMBL	Phase 3	PPARA
TESAGLITAZAR	ChEMBL	Phase 3	PPARA
CLOFIBRIC ACID	ChEMBL	Phase 2	PPARA
DIHOMO-GAMMA-LINOLENIC ACID	ChEMBL	Phase 2	PPARA
FARGLITAZAR	ChEMBL	Phase 2	PPARA
GW501516	ChEMBL	Phase 2	PPARA
GW590735	ChEMBL	Phase 2	PPARA
INDEGLITAZAR	ChEMBL	Phase 2	PPARA
LINOLEIC ACID	ChEMBL	Phase 2	PPARA
LY-518674	ChEMBL	Phase 2	PPARA
NAVEGLITAZAR	ChEMBL	Phase 2	PPARA
OLEIC ACID	ChEMBL	Phase 2	PPARA
PIRINIXIC ACID	ChEMBL	Phase 2	PPARA
RAGAGLITAZAR	ChEMBL	Phase 2	PPARA
REGLITAZAR	ChEMBL	Phase 2	PPARA
URSOLIC ACID	ChEMBL	Phase 2	PPARA
Bosentan	PubChem	Approved	PPARA
regorafenib	PubChem	Approved	PPARA