Quinacrine

Summary

Quinacrine (CHEMBL7568) is an approved small-molecule EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor (ATC P01AX05); indicated across 6 conditions including amebiasis and renal cell carcinoma.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: P01AX05
• Indications: 6 conditions
• Clinical trials: 5
• Chemistry: 400 Da · C23H30ClN3O

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL7568
Name	Quinacrine
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	237
ChEBI	CHEBI:8711
ATC	P01AX05
Molecular formula	C23H30ClN3O
Molecular weight	400
InChIKey	GPKJTRJOBQGKQK-UHFFFAOYSA-N

SMILES: CCN(CC)CCCC(C)NC1=C2C=C(C=CC2=NC3=C1C=CC(=C3)Cl)OC

IUPAC name: 4-N-(6-chloro-2-methoxyacridin-9-yl)-1-N,1-N-diethylpentane-1,4-diamine

ChEBI definition: A member of the class of acridines that is acridine substituted by a chloro group at position 6, a methoxy group at position 2 and a [5-(diethylamino)pentan-2-yl]nitrilo group at position 9.

Pharmacological roles (ChEBI): antimalarial, EC 1.8.1.12 (trypanothione-disulfide reductase) inhibitor.

Also known as: Atabrine, GNF-Pf-5448, Mepacrina, Mepacrine, Quinacrine, quinacrine, mepacrine, SID90341425, SID124881289, SID50111199, Quinacrin, MEPACRINE

Parent form; salt/anhydrous children: CHEMBL546257, CHEMBL554190, CHEMBL556980, CHEMBL2105615

Patent coverage: 5,430 distinct patent families (20,112 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 20,028 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 41 (assay-derived). Sample: Ubiquitin carboxyl-terminal hydrolase 2, NPC intracellular cholesterol transporter 1, Ras-related protein Rab-9A, Aldehyde oxidase 1, Muscarinic acetylcholine receptor M4, Alpha-2A adrenergic receptor, Alpha-2C adrenergic receptor, Histamine H2 receptor, Alpha-2B adrenergic receptor, Riboflavin-binding protein, Muscarinic acetylcholine receptor M5, D(1A) dopamine receptor, Cyclooxygenase, Sodium channel alpha subunits; brain (Types I, II, III), Muscarinic acetylcholine receptor M2, 5-hydroxytryptamine receptor 1A, Muscarinic acetylcholine receptor M1, Acetylcholinesterase, Sodium-dependent noradrenaline transporter, Alpha-1D adrenergic receptor.

Bioactivity

ChEMBL activities: 49 potent at pChembl ≥ 5 of 67 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
P04925	7.02	IC50	95.1	nM	CHEMBL_ACT_24857862
CHRM3	6.58	Ki	266	nM	CHEMBL_ACT_7746073
P02752	6.58	Kd	264	nM	CHEMBL_ACT_8028750
CHRM4	6.56	Ki	277	nM	CHEMBL_ACT_7746075
PRNP	6.52	EC50	300	nM	CHEMBL_ACT_841579
CHRM2	6.46	Ki	343	nM	CHEMBL_ACT_7746071
CHRM1	6.45	Ki	359	nM	CHEMBL_ACT_7746069
DRD3	6.35	Ki	448	nM	CHEMBL_ACT_7746011
ADRA2C	6.25	Ki	560	nM	CHEMBL_ACT_7743921
KCNH2	6.16	AC50	700	nM	CHEMBL_ACT_25117904
HRH3	6.16	AC50	692.8	nM	CHEMBL_ACT_25199677
CHRM2	6.12	AC50	767.8	nM	CHEMBL_ACT_25195881
HTR2A	6.12	Ki	761	nM	CHEMBL_ACT_7713973
ADRA2B	6.08	Ki	833	nM	CHEMBL_ACT_7743919
ADRA2A	6.07	Ki	855	nM	CHEMBL_ACT_7743917
ACHE	6.03	AC50	928.2	nM	CHEMBL_ACT_25142693
CHRM2	6.02	IC50	964	nM	CHEMBL_ACT_7746070
ADRA1D	5.99	Ki	1015	nM	CHEMBL_ACT_7743915
CHRM3	5.9	IC50	1255	nM	CHEMBL_ACT_7746072
DRD3	5.88	IC50	1318	nM	CHEMBL_ACT_7746010
CHRM1	5.83	IC50	1489	nM	CHEMBL_ACT_7746068
ADRA2B	5.74	IC50	1825	nM	CHEMBL_ACT_7743918
P15823	5.72	Ki	1890	nM	CHEMBL_ACT_7743913
CHRM4	5.7	IC50	1983	nM	CHEMBL_ACT_7746074
ADRA1D	5.68	IC50	2065	nM	CHEMBL_ACT_7743914
HTR1A	5.65	AC50	2261	nM	CHEMBL_ACT_25165169
ADRA2A	5.64	IC50	2280	nM	CHEMBL_ACT_7743916
HTR2A	5.58	IC50	2663	nM	CHEMBL_ACT_7713972
ACHE	5.57	IC50	2667	nM	CHEMBL_ACT_7743900
CHRM5	5.57	Ki	2684	nM	CHEMBL_ACT_7746077
SLC6A2	5.54	IC50	2896	nM	CHEMBL_ACT_7743928
SLC6A2	5.54	Ki	2872	nM	CHEMBL_ACT_7743929
SCN1A	5.48	IC50	3300	nM	CHEMBL_ACT_383646
AOX1	5.48	IC50	3300	nM	CHEMBL_ACT_5102810
P15823	5.47	IC50	3414	nM	CHEMBL_ACT_7743912
HRH2	5.46	Ki	3476	nM	CHEMBL_ACT_7746043
HRH2	5.45	IC50	3535	nM	CHEMBL_ACT_7746042
CHRM5	5.43	IC50	3736	nM	CHEMBL_ACT_7746076
ADRA2C	5.41	IC50	3857	nM	CHEMBL_ACT_7743920
P81908	5.35	IC50	4500	nM	CHEMBL_ACT_6219116
P22002	5.28	IC50	5200	nM	CHEMBL_ACT_15373250
O35505	5.25	IC50	5600	nM	CHEMBL_ACT_15777549
OPRM1	5.23	AC50	5862	nM	CHEMBL_ACT_25158320
P02752	5.17	Ki	6700	nM	CHEMBL_ACT_8028744
CGAS	5.16	IC50	7000	nM	CHEMBL_ACT_24707270
CGAS	5.16	IC50	7000	nM	CHEMBL_ACT_24707304
SLC6A2	5.16	AC50	6924	nM	CHEMBL_ACT_25146145
DRD3	5.15	AC50	7048	nM	CHEMBL_ACT_25194664
P80456	5	IC50	10000	nM	CHEMBL_ACT_5102835

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

1 approved indication. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).

Indication	Phase	MONDO	EFO
amebiasis	4	MONDO:0005644	EFO:0007144

4 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
renal cell carcinoma	2	MONDO:0005086	EFO:0000681
Creutzfeldt Jacob disease	2	MONDO:0005357	EFO:0004226
colorectal adenocarcinoma	1	MONDO:0005008	EFO:0000365
non-small cell lung carcinoma	1	MONDO:0005233	EFO:0003060

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 5.

Phase distribution

Phase	Trials
PHASE2	3
PHASE1/PHASE2	1
Not specified	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00183092	PHASE2	COMPLETED	CJD (Creutzfeldt-Jakob Disease) Quinacrine Study
NCT00417274	PHASE2	COMPLETED	Quinacrine Treatment in Patients With Androgen-Independent Prostate Cancer
NCT00574483	PHASE2	WITHDRAWN	Treatment of Advanced Renal Cell Carcinoma With Quinacrine
NCT01844076	PHASE1/PHASE2	TERMINATED	Quinacrine-Capecitabine Combinatorial Therapy for Advanced Stage Colorectal Adenocarcinoma
NCT00104663	Not specified	COMPLETED	PRION-1: Quinacrine for Human Prion Disease

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

PharmGKB dosing guidelines (1) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):

Guideline	Source	Gene(s)	Dosing	Recommendation
Annotation of CPIC Guideline for chlorpropamide, dabrafenib, gliclazid	CPIC	G6PD

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).