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
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)
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 | ( + / - ) |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/mmx/mepacrine.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15569390
Curator's Comment: Yung 2004, found that quinacrine does pass the blood-brain barrier in mice.
Originator
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | Atabrine Approved UseFor the treatment of ascites due to various cancers, malaria, cestodiasis and giardiasis. |
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Primary | Atabrine Approved UseFor the treatment of ascites due to various cancers, malaria, cestodiasis and giardiasis. Launch Date1964 |
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Curative | Atabrine Approved UseFor the treatment of ascites due to various cancers, malaria, cestodiasis and giardiasis. |
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Curative | Atabrine Approved UseFor the treatment of ascites due to various cancers, malaria, cestodiasis and giardiasis. |
Doses
Dose | Population | Adverse 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) Sources: Blood alkaline phosphatase abnormal (3 patients) ALT increased (3 patients) Aspartate aminotransferase abnormal (3 patients) GGTP abnormal (3 patients) Seizure (serious, 1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 0.013 uM] | ||||
yes [IC50 3.96 uM] | ||||
yes [IC50 6.66 uM] | ||||
yes [IC50 8.66 uM] | ||||
yes [IC50 >50 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
minor | ||||
minor | ||||
minor | ||||
minor | ||||
minor | ||||
minor | ||||
minor | ||||
unlikely | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Anti-cryptosporidial drug activity screened with an immunosuppressed rat model. | 1991 Nov-Dec |
|
Antimalarial therapy: a panacea for mild lupus? | 2001 |
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Involvement of calcium signaling in the fibronectin-stimulated macrophage recognition of oxidatively damaged erythrocytes. | 2001 Apr 23 |
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Acquired storage-pool disorders occurring late after allogeneic bone marrow transplantation: partial activation of platelets in asymptomatic patients. | 2001 Aug |
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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 |
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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 |
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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 |
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High-throughput measurement of the Tp53 response to anticancer drugs and random compounds using a stably integrated Tp53-responsive luciferase reporter. | 2002 Jun |
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Participation of the arachidonic acid cascade pathway in macrophage binding/uptake of oxidized low density lipoprotein. | 2002 Jun |
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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 |
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Histamine release by hydrochloric acid is mediated via reactive oxygen species generation and phospholipase D in RBL-2H3 mast cells. | 2002 Oct |
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Contribution of different phospholipases and arachidonic acid metabolites in the response of gallbladder smooth muscle to cholecystokinin. | 2002 Oct 1 |
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Synthesis and antiinflammatory evaluation of 9-anilinoacridine and 9-phenoxyacridine derivatives. | 2002 Oct 10 |
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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 |
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Flow cytometric findings in platelets of patients following allogeneic hematopoietic stem cell transplantation. | 2002 Sep |
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Further evidence that the CCK2 receptor is coupled to two transduction pathways using site-directed mutagenesis. | 2003 Apr |
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Quinacrine-induced cytolytic hepatitis in sporadic Creutzfeldt-Jakob disease. | 2003 Apr |
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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 |
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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 |
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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
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25288082
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
Edited
Fri Dec 15 15:05:52 GMT 2023
by
admin
on
Fri Dec 15 15:05:52 GMT 2023
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Record UNII |
H0C805XYDE
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
379912
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WHO-ATC |
P01AX05
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FDA ORPHAN DRUG |
820321
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WHO-VATC |
QP51AX04
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FDA ORPHAN DRUG |
701119
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m9430
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H0C805XYDE
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49845
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65960-40-9
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201-508-7
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100000085652
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CHEMBL7568
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3253
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SUB08744MIG
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C87656
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D011796
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H0C805XYDE
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DTXSID7022627
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2338
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65960-39-6
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ALTERNATIVE | |||
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MEPACRINE
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR | |||
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METABOLIC ENZYME -> INHIBITOR |
IC50
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Related Record | Type | Details | ||
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ACTIVE MOIETY |