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
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
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 |
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 |
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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 |
---|---|---|
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
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 15:12:37 GMT 2023
by
admin
on
Fri Dec 15 15:12:37 GMT 2023
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Record UNII |
G6242H2NAA
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Record Status |
Validated (UNII)
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Record Version |
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FDA ORPHAN DRUG |
4184
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NCI_THESAURUS |
C274
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m9430
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SUB03152MIG
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE |
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ACTIVE MOIETY |