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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Atabrine
Primary
Atabrine
Curative
Atabrine
Curative
Atabrine

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Capsule: 25‐200 mg, Suppositories: 25-100 mg.
Route of Administration: Other
In Vitro Use Guide
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
Record UNII
H0C805XYDE
Record Status Validated (UNII)
Record Version