Chloroquine

Chloroquine
Clinical data
Pronunciation	/ˈklɔːrəkwiːn/
Trade names	Aralen, other
Other names	Chloroquine phosphate
AHFS/Drugs.com	Monograph
License data	US DailyMed: Chloroquine;
Routes of; administration	By mouth
ATC code	P01BA01 (WHO) P01BB52 (WHO);
Legal status
Legal status	UK: P (Pharmacy medicines); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolism	Liver
Elimination half-life	1-2 months
Identifiers
	IUPAC name (RS)-N'-(7-chloroquinolin-4-yl)-N,N-diethylpentane-1,4-diamine;
CAS Number	54-05-7 ;
PubChem CID	2719;
IUPHAR/BPS	5535;
DrugBank	DB00608 ;
ChemSpider	2618 ;
UNII	886U3H6UFF;
KEGG	D02366 ;
ChEBI	CHEBI:3638 ;
ChEMBL	ChEMBL76 ;
NIAID ChemDB	000733;
CompTox Dashboard (EPA)	DTXSID2040446 ;
ECHA InfoCard	100.000.175
Chemical and physical data
Formula	C18H26ClN3
Molar mass	319.88 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1cc2nccc(c2cc1)NC(C)CCCN(CC)CC;
	InChI InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21) ; Key:WHTVZRBIWZFKQO-UHFFFAOYSA-N ;
	(verify)

Chloroquine is an antiparasitic medication that treats malaria. It works by increasing the levels of heme in the blood, a substance toxic to the malarial parasite. This kills the parasite and stops the infection from spreading. Certain types of malaria, resistant strains, and complicated cases typically require different or additional medication. Chloroquine is also occasionally used for amebiasis that is occurring outside the intestines, rheumatoid arthritis, and lupus erythematosus. While it has not been formally studied in pregnancy, it appears safe. It is taken by mouth. It was studied to treat COVID-19 early in the pandemic, but these studies were largely halted in the northern summer of 2020, and the NIH does not recommend its use for this purpose.

Common side effects include muscle problems, loss of appetite, diarrhea, and skin rash. Serious side effects include problems with vision, muscle damage, seizures, and low blood cell levels. Chloroquine is a member of the drug class 4-aminoquinoline. As an antimalarial, it works against the asexual form of the malaria parasite in the stage of its life cycle within the red blood cell. How it works in rheumatoid arthritis and lupus erythematosus is unclear.

Chloroquine was discovered in 1934 by Hans Andersag. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.