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Details

Stereochemistry RACEMIC
Molecular Formula C23H30ClN3O.2ClH.2H2O
Molecular Weight 508.909
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of QUINACRINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=RZFNKJVCPDLQQA-UHFFFAOYSA-N
InChI=1S/C23H30ClN3O.2ClH.2H2O/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);2*1H;2*1H2

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 ( + / - )

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
RETINOPATHY DURING CHLOROQUINE THERAPY.
1961 Nov
Anti-cryptosporidial drug activity screened with an immunosuppressed rat model.
1991 Nov-Dec
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Involvement of calcium signaling in the fibronectin-stimulated macrophage recognition of oxidatively damaged erythrocytes.
2001 Apr 23
Two distinct mechanisms are involved in stent thrombosis under flow conditions.
2001 Jun
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
[Creutzfeldt-Jakob disease: diagnosis, incidence, prevention and treatment].
2002 Apr 20
Involvement of oxidative stress in bee venom-induced inhibition of Na+/glucose cotransporter in renal proximal tubule cells.
2002 Jul
Involvement of glycoprotein VI in platelet thrombus formation on both collagen and von Willebrand factor surfaces under flow conditions.
2002 Jul 9
Participation of the arachidonic acid cascade pathway in macrophage binding/uptake of oxidized low density lipoprotein.
2002 Jun
High glucose down-regulates angiotensin II binding via the PKC-MAPK-cPLA2 signal cascade in renal proximal tubule cells.
2002 Mar
Regulation of reactive oxygen species and stress fiber formation by calpeptin in Swiss 3T3 fibroblasts.
2002 Mar
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
Effects of cholesterol on dye leakage induced by multidrug-resistance modulators from anionic liposomes.
2003 Jan
Effect of epinephrine on alpha-methyl-D-glucopyranoside uptake in renal proximal tubule cells.
2004
Assessment of platelet activation in myeloproliferative disorders with complementary techniques.
2004 Apr
Oral mucosal pigmentation secondary to treatment with mepacrine, with sparing of the denture bearing area.
2004 Aug
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
Cyclic stretch-induced cPLA2 mediates ERK 1/2 signaling in rabbit proximal tubule cells.
2004 Feb
[Creutzfeldt-Jakob disease, Heidenhain variant: case report with MRI (DWI) findings].
2004 Jun
Oxalate inhibits renal proximal tubule cell proliferation via oxidative stress, p38 MAPK/JNK, and cPLA2 signaling pathways.
2004 Oct
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
Role of contractile prostaglandins and Rho-kinase in growth factor-induced airway smooth muscle contraction.
2005 Jul 27
Blood schizontocidal activity of azithromycin and its combination with alpha/beta arteether against multi-drug resistant Plasmodium yoelii nigeriensis, a novel MDR parasite model for antimalarial screening.
2005 Sep
In vitro antiproliferative effects of neuroleptics, antimycotics and antibiotics on the human pathogens Acanthamoeba polyphaga and Naegleria fowleri.
2006 Aug
Hypoxia-induced sickness behaviour.
2006 Nov
Randomized clinical study of five days apostrophe therapy with mebendazole compared to quinacrine in the treatment of symptomatic giardiasis in children.
2006 Oct 21
Oral given Mepacrine could increase the resistance to heat environment injury.
2007
Role of phospholipase D2 in anti-apoptotic signaling through increased expressions of Bcl-2 and Bcl-xL.
2007 Aug 15
HPA-1 polymorphism of alphaIIbbeta3 modulates platelet adhesion onto immobilized fibrinogen in an in-vitro flow system.
2007 Feb 19
Involvement of free radicals followed by the activation of phospholipase A2 in the mechanism that underlies the combined effects of methamphetamine and morphine on subacute toxicity or lethality in mice: comparison of the therapeutic potential of fullerene, mepacrine, and cooling.
2007 Jul 17
Drug, dosage, activity, studies of antimalarials by physical methods--II.
2007 May 20
Roles of brain phosphatidylinositol-specific phospholipase C and diacylglycerol lipase in centrally administered histamine-induced adrenomedullary outflow in rats.
2007 Oct 1
Mepacrine alleviates airway hyperresponsiveness and airway inflammation in a mouse model of asthma.
2008 Jun
Plasmodium vivax trophozoites insensitive to chloroquine.
2008 May 27
Diaryl sulfide-based inhibitors of trypanothione reductase: inhibition potency, revised binding mode and antiprotozoal activities.
2008 Nov 7
ATP-induced apoptosis involves a Ca2+-independent phospholipase A2 and 5-lipoxygenase in macrophages.
2009 Jan
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 15:12:37 GMT 2023
Edited
by admin
on Fri Dec 15 15:12:37 GMT 2023
Record UNII
G6242H2NAA
Record Status Validated (UNII)
Record Version
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Name Type Language
QUINACRINE HYDROCHLORIDE
VANDF  
Common Name English
QUINACRINE HYDROCHLORIDE DIHYDRATE
Common Name English
6-Chloro-9-[[4-(diethylamino)-1-methylbutyl]amino]-2-methoxyacridine dihydrochloride dihydrate
Systematic Name English
NSC-757307
Code English
QUINACRINE HCL
Common Name English
QUINACRINE DIHYDROCHLORIDE DIHYDRATE [MI]
Common Name English
QUINACRINE HYDROCHLORIDE [VANDF]
Common Name English
MEPACRINE HYDROCHLORIDE
Common Name English
(±)-6-CHLORO-9-((4-(DIETHYLAMINO)-1-METHYLBUTYL)AMINO)-2-METHOXYACRIDINE DIHYDROCHLORIDE DIHYDRATE
Systematic Name English
MEPACRINE HYDROCHLORIDE DIHYDRATE
Common Name English
MEPACRINE DIHYDROCHLORIDE DIHYDRATE
Common Name English
QUINACRINE DIHYDROCHLORIDE DIHYDRATE
MI  
Common Name English
ATABRINE HYDROCHLORIDE
Brand Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 4184
Created by admin on Fri Dec 15 15:12:37 GMT 2023 , Edited by admin on Fri Dec 15 15:12:37 GMT 2023
NCI_THESAURUS C274
Created by admin on Fri Dec 15 15:12:37 GMT 2023 , Edited by admin on Fri Dec 15 15:12:37 GMT 2023
Code System Code Type Description
MERCK INDEX
m9430
Created by admin on Fri Dec 15 15:12:37 GMT 2023 , Edited by admin on Fri Dec 15 15:12:37 GMT 2023
PRIMARY Merck Index
EVMPD
SUB03152MIG
Created by admin on Fri Dec 15 15:12:37 GMT 2023 , Edited by admin on Fri Dec 15 15:12:37 GMT 2023
PRIMARY
ChEMBL
CHEMBL7568
Created by admin on Fri Dec 15 15:12:37 GMT 2023 , Edited by admin on Fri Dec 15 15:12:37 GMT 2023
PRIMARY
DRUG BANK
DBSALT002386
Created by admin on Fri Dec 15 15:12:37 GMT 2023 , Edited by admin on Fri Dec 15 15:12:37 GMT 2023
PRIMARY
PUBCHEM
2725002
Created by admin on Fri Dec 15 15:12:37 GMT 2023 , Edited by admin on Fri Dec 15 15:12:37 GMT 2023
PRIMARY
NSC
757307
Created by admin on Fri Dec 15 15:12:37 GMT 2023 , Edited by admin on Fri Dec 15 15:12:37 GMT 2023
PRIMARY
FDA UNII
G6242H2NAA
Created by admin on Fri Dec 15 15:12:37 GMT 2023 , Edited by admin on Fri Dec 15 15:12:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID8045565
Created by admin on Fri Dec 15 15:12:37 GMT 2023 , Edited by admin on Fri Dec 15 15:12:37 GMT 2023
PRIMARY
NCI_THESAURUS
C67059
Created by admin on Fri Dec 15 15:12:37 GMT 2023 , Edited by admin on Fri Dec 15 15:12:37 GMT 2023
PRIMARY
CAS
6151-30-0
Created by admin on Fri Dec 15 15:12:37 GMT 2023 , Edited by admin on Fri Dec 15 15:12:37 GMT 2023
PRIMARY
SMS_ID
100000086419
Created by admin on Fri Dec 15 15:12:37 GMT 2023 , Edited by admin on Fri Dec 15 15:12:37 GMT 2023
PRIMARY
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