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=CC(Cl)=CC2=NC3=CC=C(OC)C=C13
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. |
|||
| Primary | Atabrine Approved UseFor the treatment of ascites due to various cancers, malaria, cestodiasis and giardiasis. Launch Date1964 |
|||
| Curative | Atabrine Approved UseFor the treatment of ascites due to various cancers, malaria, cestodiasis and giardiasis. |
|||
| 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) Health Status: unhealthy Age Group: 60.5 years (range: 40–75 years) Sex: M+F 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) Health Status: unhealthy Age Group: 60.5 years (range: 40–75 years) Sex: M+F 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) Health Status: unhealthy Age Group: 60.5 years (range: 40–75 years) Sex: M+F 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) Health Status: unhealthy Age Group: 60.5 years (range: 40–75 years) Sex: M+F 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) Health Status: unhealthy Age Group: 60.5 years (range: 40–75 years) Sex: M+F 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) Health Status: unhealthy Age Group: 60.5 years (range: 40–75 years) Sex: M+F 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) Health Status: unhealthy Age Group: 60.5 years (range: 40–75 years) Sex: M+F 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 |
|---|---|---|
| Inhibition of rat hepatic CYP2E1 by quinacrine: molecular modeling investigation and effects on 4-(methyl nitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced mutagenicity. | 2009-06 |
|
| Binge ethanol-induced neurodegeneration in rat organotypic brain slice cultures: effects of PLA2 inhibitor mepacrine and docosahexaenoic acid (DHA). | 2009-02 |
|
| ATP-induced apoptosis involves a Ca2+-independent phospholipase A2 and 5-lipoxygenase in macrophages. | 2009-01 |
|
| Post partum haemorrhage secondary to uterine atony, complicated by platelet storage pool disease and partial placenta diffusa: a case report. | 2008-12-13 |
|
| Bradykinin stimulates glutamate uptake via both B1R and B2R activation in a human retinal pigment epithelial cells. | 2008-12-05 |
|
| Mepacrine antagonises tumour cell growth induced by natural polyamines. | 2008-11-28 |
|
| Diaryl sulfide-based inhibitors of trypanothione reductase: inhibition potency, revised binding mode and antiprotozoal activities. | 2008-11-07 |
|
| The three-dimensional hydrogen-bonded framework structure in the 1:1 proton-transfer compound of the drug quinacrine with 5-sulfosalicylic acid. | 2008-08 |
|
| Mepacrine alleviates airway hyperresponsiveness and airway inflammation in a mouse model of asthma. | 2008-06 |
|
| Plasmodium vivax trophozoites insensitive to chloroquine. | 2008-05-27 |
|
| Overexpression of phospholipase D suppresses taxotere-induced cell death in stomach cancer cells. | 2008-05 |
|
| Comparison of nitric oxide synthase inhibitors, phospholipase A2 inhibitor and free radical scavengers as attenuators of opioid withdrawal syndrome. | 2007-12 |
|
| Roles of brain phosphatidylinositol-specific phospholipase C and diacylglycerol lipase in centrally administered histamine-induced adrenomedullary outflow in rats. | 2007-10-01 |
|
| Role of phospholipase D2 in anti-apoptotic signaling through increased expressions of Bcl-2 and Bcl-xL. | 2007-08-15 |
|
| Effects of age-dependent membrane transport changes on the homeostasis of senescent human red blood cells. | 2007-08-15 |
|
| 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. | 2007-07-17 |
|
| Drug, dosage, activity, studies of antimalarials by physical methods--II. | 2007-05-20 |
|
| Platelet adhesion onto immobilized fibrinogen under arterial and venous in-vitro flow conditions does not significantly differ between men and women. | 2007-04-26 |
|
| HPA-1 polymorphism of alphaIIbbeta3 modulates platelet adhesion onto immobilized fibrinogen in an in-vitro flow system. | 2007-02-19 |
|
| Phospholipase D1 as a key enzyme for decidualization in human endometrial stromal cells. | 2007-02 |
|
| Uric acid inhibits renal proximal tubule cell proliferation via at least two signaling pathways involving PKC, MAPK, cPLA2, and NF-kappaB. | 2007-01 |
|
| The effects by neuroleptics, antimycotics and antibiotics on disulfide reducing enzymes from the human pathogens Acanthamoeba polyphaga and Naegleria fowleri. | 2007-01 |
|
| Hydrogen peroxide increases [3H]-2-deoxyglucose uptake via MAPKs, cPLA2, and NF-kappaB signaling pathways in mouse embryonic stem cells. | 2007 |
|
| Oral given Mepacrine could increase the resistance to heat environment injury. | 2007 |
|
| Roles of P2 receptors in glial cells: focus on astrocytes. | 2006-11 |
|
| Hypoxia-induced sickness behaviour. | 2006-11 |
|
| Randomized clinical study of five days apostrophe therapy with mebendazole compared to quinacrine in the treatment of symptomatic giardiasis in children. | 2006-10-21 |
|
| Antithrombin significantly influences platelet adhesion onto immobilized fibrinogen in an in-vitro system simulating low flow. | 2006-10-13 |
|
| Activity of picolinic acid in combination with the antiprotozoal drug quinacrine against Mycobacterium avium complex. | 2006-09 |
|
| In vitro antiproliferative effects of neuroleptics, antimycotics and antibiotics on the human pathogens Acanthamoeba polyphaga and Naegleria fowleri. | 2006-08 |
|
| Mechanism of induction of muscle protein degradation by angiotensin II. | 2006-07 |
|
| Arachidonic acid induces ERK activation via Src SH2 domain association with the epidermal growth factor receptor. | 2006-05 |
|
| The reduction of serum B-lymphocyte activating factor levels following quinacrine add-on therapy in systemic lupus erythematosus. | 2006-04 |
|
| A novel role of phospholipase A2 in mediating spinal cord secondary injury. | 2006-04 |
|
| Prion diseases: current understanding of epidemiology and pathogenesis, and therapeutic advances. | 2006 |
|
| 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. | 2005-09 |
|
| High cystine in platelets from patients with nephropathic cystinosis: a chemical, ultrastructural, and functional evaluation. | 2005-09 |
|
| In vitro synergy and enhanced murine brain penetration of saquinavir coadministered with mefloquine. | 2005-09 |
|
| Acridine derivatives activate p53 and induce tumor cell death through Bax. | 2005-08 |
|
| Role of contractile prostaglandins and Rho-kinase in growth factor-induced airway smooth muscle contraction. | 2005-07-27 |
|
| 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). | 2005-06 |
|
| Brain phospholipase C/diacylglycerol lipase are involved in bombesin BB2 receptor-mediated activation of sympatho-adrenomedullary outflow in rats. | 2005-05-09 |
|
| Serum ferritin elevation and acute lung injury in rats subjected to hemorrhage: reduction by mepacrine treatment. | 2004-09-17 |
|
| Scar sarcoidosis following tattooing of the lips treated with mepacrine. | 2004-09 |
|
| Involvement of protein kinase C activation in L-leucine-induced stimulation of protein synthesis in l6 myotubes. | 2003-11 |
|
| Possible involvement of phospholipase C and protein kinase C in stimulatory actions of L-leucine and its keto acid, alpha-ketoisocaproic acid, on protein synthesis in RLC-16 hepatocytes. | 2002-11 |
|
| Camp laparoscopic sterilization deaths in Gujarat State, India, 1978-1980. | 1991-12 |
|
| Anti-cryptosporidial drug activity screened with an immunosuppressed rat model. | 1991-11-01 |
|
| A Comparative Study of Hymenolepicides in Hymenolepis Mana Infestation of Rats. | 1962-07 |
|
| RETINOPATHY DURING CHLOROQUINE THERAPY. | 1961-11 |
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
Mon Mar 31 17:46:21 GMT 2025
by
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Mon Mar 31 17:46:21 GMT 2025
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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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| Code System | Code | Type | Description | ||
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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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396
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DB01103
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83-89-6
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8711
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C87656
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237
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9061
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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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ACTIVE MOIETY |