Quinacrine

Mepacrine

Clinical data
Trade names	Atabrine
AHFS/Drugs.com	Micromedex Detailed Consumer Information
ATC code	P01AX05 (WHO) QP51AX04 (WHO)
Pharmacokinetic data
Protein binding	80–90%
Biological half-life	5–14 days
Identifiers
IUPAC name (RS)-N′-(6-Chloro-2-methoxy-acridin-9-yl)-N,N-diethylpentane-1,4-diamine
CAS Number	83-89-6 Y
PubChem CID	237
DrugBank	DB01103 Y
ChemSpider	232 Y
UNII	H0C805XYDE
KEGG	D08179
ChEBI	CHEBI:8711 Y
ChEMBL	CHEMBL7568 Y
PDB ligand	QUN (PDBe, RCSB PDB)
ECHA InfoCard	100.001.371
Chemical and physical data
Formula	C23H30ClN3O
Molar mass	399.957 g/mol
3D model (Jmol)	Interactive image
SMILES CCN(CC)CCCC(C)Nc1c2ccc(cc2nc3c1cc(cc3)OC)Cl
InChI 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) Y Key:GPKJTRJOBQGKQK-UHFFFAOYSA-N Y

Mepacrine (INN), also called quinacrine (USAN) or by the trade name Atabrine, is a drug with several medical applications. It is related to chloroquine and mefloquine.

The main uses of mepacrine are as an antiprotozoal, antirheumatic and an intrapleural sclerosing agent.

Antiprotozoal use include targeting giardiasis, where mepacrine is indicated as a primary agent for patients with metronidazole-resistant giardiasis and patients who should not receive or can not tolerate metronidazole. Giardiasis that is very resistant may even require a combination of mepacrine and metronidazole.

Mepacrine is also used off-label for the treatment of systemic lupus erythematosus, indicated in the treatment of discoid and subcutaneous lupus erythematosus, particularly in patients unable to take chloroquine derivatives.

As an intrapleural sclerosing agent, it is used as pneumothorax prophylaxis in patients at high risk of recurrence, e.g., cystic fibrosis patients.

Mepacrine is not the drug of choice because side effects are common, including toxic psychosis, and may cause permanent damage. See mefloquine for more information.

In addition to medical applications, mepacrine is an effective in vitro research tool for the epifluorescent visualization of cells, especially platelets. Mepacrine is a green fluorescent dye taken up by most cells. Platelets store mepacrine in dense granules.

Its mechanism of action against protozoa is uncertain, but it is thought to act against the protozoan's cell membrane.