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Details

Stereochemistry RACEMIC
Molecular Formula C23H30ClN3O
Molecular Weight 399.957
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUINACRINE

SMILES

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

InChI

InChIKey=GPKJTRJOBQGKQK-UHFFFAOYSA-N
InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)

HIDE SMILES / InChI

Molecular Formula C23H30ClN3O
Molecular Weight 399.957
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/mmx/mepacrine.html

Quinacrine was initially developed as an anti-malarial drug marketed under the name Atabrine. Also it was approved for the teratment of ascites, however it was wothdrawn for both indication in 1995 and 2003, respectively. The drug is also used for the treatment of giardiasis, lupus, rheumatoid arthritis, refractory pulmonary effusion and pneumothorax, induce female sterilization etc. Proposed mechanisms of action include DNA intercalation interference with RNA transcription and translation, inhibition of succinate oxidation interference with electron transport, inhibition of cholinesterase, and inhibitor of phospholipase.

CNS Activity

Curator's Comment: Yung 2004, found that quinacrine does pass the blood-brain barrier in mice.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Atabrine

Approved Use

For the treatment of ascites due to various cancers, malaria, cestodiasis and giardiasis.
Primary
Atabrine

Approved Use

For the treatment of ascites due to various cancers, malaria, cestodiasis and giardiasis.

Launch Date

1964
Curative
Atabrine

Approved Use

For the treatment of ascites due to various cancers, malaria, cestodiasis and giardiasis.
Curative
Atabrine

Approved Use

For the treatment of ascites due to various cancers, malaria, cestodiasis and giardiasis.
Doses

Doses

DosePopulationAdverse events​
300 mg 1 times / day multiple, oral
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 60.5 years (range: 40–75 years)
n = 23
Health Status: unhealthy
Condition: sporadic Creutzfeldt-Jakob disease
Age Group: 60.5 years (range: 40–75 years)
Sex: M+F
Population Size: 23
Sources:
Other AEs: Distress gastrointestinal, Blood alkaline phosphatase abnormal...
Other AEs:
Distress gastrointestinal (serious, 1 patient)
Blood alkaline phosphatase abnormal (3 patients)
ALT increased (3 patients)
Aspartate aminotransferase abnormal (3 patients)
GGTP abnormal (3 patients)
Seizure (serious, 1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
ALT increased 3 patients
300 mg 1 times / day multiple, oral
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 60.5 years (range: 40–75 years)
n = 23
Health Status: unhealthy
Condition: sporadic Creutzfeldt-Jakob disease
Age Group: 60.5 years (range: 40–75 years)
Sex: M+F
Population Size: 23
Sources:
Aspartate aminotransferase abnormal 3 patients
300 mg 1 times / day multiple, oral
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 60.5 years (range: 40–75 years)
n = 23
Health Status: unhealthy
Condition: sporadic Creutzfeldt-Jakob disease
Age Group: 60.5 years (range: 40–75 years)
Sex: M+F
Population Size: 23
Sources:
Blood alkaline phosphatase abnormal 3 patients
300 mg 1 times / day multiple, oral
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 60.5 years (range: 40–75 years)
n = 23
Health Status: unhealthy
Condition: sporadic Creutzfeldt-Jakob disease
Age Group: 60.5 years (range: 40–75 years)
Sex: M+F
Population Size: 23
Sources:
GGTP abnormal 3 patients
300 mg 1 times / day multiple, oral
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 60.5 years (range: 40–75 years)
n = 23
Health Status: unhealthy
Condition: sporadic Creutzfeldt-Jakob disease
Age Group: 60.5 years (range: 40–75 years)
Sex: M+F
Population Size: 23
Sources:
Distress gastrointestinal serious, 1 patient
300 mg 1 times / day multiple, oral
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 60.5 years (range: 40–75 years)
n = 23
Health Status: unhealthy
Condition: sporadic Creutzfeldt-Jakob disease
Age Group: 60.5 years (range: 40–75 years)
Sex: M+F
Population Size: 23
Sources:
Seizure serious, 1 patient
300 mg 1 times / day multiple, oral
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, 60.5 years (range: 40–75 years)
n = 23
Health Status: unhealthy
Condition: sporadic Creutzfeldt-Jakob disease
Age Group: 60.5 years (range: 40–75 years)
Sex: M+F
Population Size: 23
Sources:
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Anti-cryptosporidial drug activity screened with an immunosuppressed rat model.
1991 Nov-Dec
Antimalarial therapy: a panacea for mild lupus?
2001
Involvement of calcium signaling in the fibronectin-stimulated macrophage recognition of oxidatively damaged erythrocytes.
2001 Apr 23
Acquired storage-pool disorders occurring late after allogeneic bone marrow transplantation: partial activation of platelets in asymptomatic patients.
2001 Aug
Epinephrine--via activation of p38-MAPK--abolishes the effect of aspirin on platelet deposition to collagen.
2001 Dec 15
Role of the cytosolic phospholipase A2-linked cascade in signaling by an oncogenic, constitutively active Ha-Ras isoform.
2001 Jul 6
ATP-induced mucin release from cultured airway goblet cell involves, in part, activation of phospholipase A2.
2001 Mar
Hypoxia alters the sensitivity of the L-type Ca(2+) channel to alpha-adrenergic receptor stimulation in the presence of beta-adrenergic receptor stimulation.
2001 May 25
tert-Butyl hydroperoxide-induced lipid signaling in hepatocytes: involvement of glutathione and free radicals.
2001 Sep 15
Verotoxin-1-induced up-regulation of adhesive molecules renders microvascular endothelial cells thrombogenic at high shear stress.
2001 Sep 15
The water-soluble fraction (<10 kD) of bee venom (Apis mellifera) produces inhibitory effect on apical transporters in renal proximal tubule cells.
2002
[Creutzfeldt-Jakob disease: diagnosis, incidence, prevention and treatment].
2002 Apr 20
Platelet flow cytometric findings in patients undergoing conditioning therapy for allogeneic hematopoietic stem cell transplantation.
2002 Aug
Stem cell factor modulates paired-pulse facilitation and long-term potentiation in the hippocampal mossy fiber-CA3 pathway in mice.
2002 Aug 16
Arachidonic acid release from rat Leydig cells: the involvement of G protein, phospholipase A2 and regulation of cAMP production.
2002 Jan
Involvement of oxidative stress in bee venom-induced inhibition of Na+/glucose cotransporter in renal proximal tubule cells.
2002 Jul
The regulation of platelet-dense granules by Rab27a in the ashen mouse, a model of Hermansky-Pudlak and Griscelli syndromes, is granule-specific and dependent on genetic background.
2002 Jul 1
Involvement of glycoprotein VI in platelet thrombus formation on both collagen and von Willebrand factor surfaces under flow conditions.
2002 Jul 9
High-throughput measurement of the Tp53 response to anticancer drugs and random compounds using a stably integrated Tp53-responsive luciferase reporter.
2002 Jun
Participation of the arachidonic acid cascade pathway in macrophage binding/uptake of oxidized low density lipoprotein.
2002 Jun
Antiprotozoals effective in vitro against the scuticociliate fish pathogen Philasterides dicentrarchi.
2002 Jun 3
Regulation of reactive oxygen species and stress fiber formation by calpeptin in Swiss 3T3 fibroblasts.
2002 Mar
Histamine release by hydrochloric acid is mediated via reactive oxygen species generation and phospholipase D in RBL-2H3 mast cells.
2002 Oct
Contribution of different phospholipases and arachidonic acid metabolites in the response of gallbladder smooth muscle to cholecystokinin.
2002 Oct 1
Synthesis and antiinflammatory evaluation of 9-anilinoacridine and 9-phenoxyacridine derivatives.
2002 Oct 10
Platelets, circulating tissue factor, and fibrin colocalize in ex vivo thrombi: real-time fluorescence images of thrombus formation and propagation under defined flow conditions.
2002 Oct 15
Flow cytometric findings in platelets of patients following allogeneic hematopoietic stem cell transplantation.
2002 Sep
Further evidence that the CCK2 receptor is coupled to two transduction pathways using site-directed mutagenesis.
2003 Apr
Quinacrine-induced cytolytic hepatitis in sporadic Creutzfeldt-Jakob disease.
2003 Apr
Effects of cholesterol on dye leakage induced by multidrug-resistance modulators from anionic liposomes.
2003 Jan
The nucleotide transporter MRP4 (ABCC4) is highly expressed in human platelets and present in dense granules, indicating a role in mediator storage.
2004 Dec 1
Platelets in patients with acute ischemic stroke are exhausted and refractory to thrombin, due to cleavage of the seven-transmembrane thrombin receptor (PAR-1).
2004 Feb
Serum ferritin elevation and acute lung injury in rats subjected to hemorrhage: reduction by mepacrine treatment.
2004 Oct-Nov
High glucose inhibits fructose uptake in renal proximal tubule cells: involvement of cAMP, PLC/PKC, p44/42 MAPK, and cPLA2.
2004 Sep
Acridine derivatives activate p53 and induce tumor cell death through Bax.
2005 Aug
Role of contractile prostaglandins and Rho-kinase in growth factor-induced airway smooth muscle contraction.
2005 Jul 27
Re: Martin TJM, Sharp I, Oral mucosal pigmentation secondary to treatment with mepacrine, with sparing of the denture bearing area (Br J Oral Maxillofac Surg 2004;42:351-3).
2005 Jun
High cystine in platelets from patients with nephropathic cystinosis: a chemical, ultrastructural, and functional evaluation.
2005 Sep
In vitro synergy and enhanced murine brain penetration of saquinavir coadministered with mefloquine.
2005 Sep
Hypoxia-induced sickness behaviour.
2006 Nov
Antithrombin significantly influences platelet adhesion onto immobilized fibrinogen in an in-vitro system simulating low flow.
2006 Oct 13
Randomized clinical study of five days apostrophe therapy with mebendazole compared to quinacrine in the treatment of symptomatic giardiasis in children.
2006 Oct 21
Comparison of nitric oxide synthase inhibitors, phospholipase A2 inhibitor and free radical scavengers as attenuators of opioid withdrawal syndrome.
2007 Dec
Phospholipase D1 as a key enzyme for decidualization in human endometrial stromal cells.
2007 Feb
Drug, dosage, activity, studies of antimalarials by physical methods--II.
2007 May 20
The three-dimensional hydrogen-bonded framework structure in the 1:1 proton-transfer compound of the drug quinacrine with 5-sulfosalicylic acid.
2008 Aug
Plasmodium vivax trophozoites insensitive to chloroquine.
2008 May 27
Binge ethanol-induced neurodegeneration in rat organotypic brain slice cultures: effects of PLA2 inhibitor mepacrine and docosahexaenoic acid (DHA).
2009 Feb
Inhibition of rat hepatic CYP2E1 by quinacrine: molecular modeling investigation and effects on 4-(methyl nitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced mutagenicity.
2009 Jun
Patents

Patents

Sample Use Guides

Capsule: 25‐200 mg, Suppositories: 25-100 mg.
Route of Administration: Other
The concentration of Quinacrine needed to reduce Candida albicans biofilm metabolic activity by 50% (sMIC50) was 256 ug/ml, and the concentration needed to reduce Candida albicans biofilm metabolic activity by 90% (sMIC90) was 1,024 ug/ml.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:05:52 GMT 2023
Edited
by admin
on Fri Dec 15 15:05:52 GMT 2023
Record UNII
H0C805XYDE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
QUINACRINE
HSDB   MI   VANDF  
Common Name English
Mepacrine [WHO-DD]
Common Name English
QUINACRINE [VANDF]
Common Name English
QUINACRINE [HSDB]
Common Name English
MEPACRINE
INN   WHO-DD  
INN  
Official Name English
ATABRINE
Brand Name English
mepacrine [INN]
Common Name English
QUINACRINE [MI]
Common Name English
6-CHLORO-9-((4-(DIETHYLAMINO)-1-METHYLBUTYL)AMINO)-2-METHOXYACRIDINE
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 379912
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
WHO-ATC P01AX05
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
FDA ORPHAN DRUG 820321
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
WHO-VATC QP51AX04
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
FDA ORPHAN DRUG 701119
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
Code System Code Type Description
MERCK INDEX
m9430
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY Merck Index
DAILYMED
H0C805XYDE
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
CHEBI
49845
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
CAS
65960-40-9
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
ALTERNATIVE
ECHA (EC/EINECS)
201-508-7
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
SMS_ID
100000085652
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
ChEMBL
CHEMBL7568
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
HSDB
3253
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
EVMPD
SUB08744MIG
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
INN
396
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
DRUG BANK
DB01103
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
CAS
83-89-6
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
CHEBI
8711
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
NCI_THESAURUS
C87656
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
PUBCHEM
237
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
RXCUI
9061
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY RxNorm
MESH
D011796
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
FDA UNII
H0C805XYDE
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
EPA CompTox
DTXSID7022627
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
DRUG CENTRAL
2338
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
CAS
65960-39-6
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
ALTERNATIVE
WIKIPEDIA
MEPACRINE
Created by admin on Fri Dec 15 15:05:52 GMT 2023 , Edited by admin on Fri Dec 15 15:05:52 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
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IC50
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ACTIVE MOIETY