Chemical Component Summary

NameN4-(7-CHLORO-QUINOLIN-4-YL)-N1,N1-DIETHYL-PENTANE-1,4-DIAMINE
SynonymsCHLOROQUINE
Identifiers(4R)-N'-(7-chloroquinolin-4-yl)-N,N-diethyl-pentane-1,4-diamine
FormulaC18 H26 Cl N3
Molecular Weight319.872
TypeNON-POLYMER
Isomeric SMILESCCN(CC)CCC[C@@H](C)Nc1ccnc2c1ccc(c2)Cl
InChIInChI=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)/t14-/m1/s1
InChIKeyWHTVZRBIWZFKQO-CQSZACIVSA-N

Chemical Details

Formal Charge0
Atom Count48
Chiral Atom Count1
Bond Count49
Aromatic Bond Count11

Drug Info: DrugBank

DrugBank IDDB00608 
NameChloroquine
Groups
  • vet_approved
  • approved
  • investigational
DescriptionChloroquine is an aminoquinolone derivative first developed in the 1940s for the treatment of malaria.[A191655] It was the drug of choice to treat malaria until the development of newer antimalarials such as [pyrimethamine], [artemisinin], and [mefloquine].[A191787] Chloroquine and its derivative [hydroxychloroquine] have since been repurposed for the treatment of a number of other conditions including HIV, systemic lupus erythematosus, and rheumatoid arthritis.[A192432] **The FDA emergency use authorization for [hydroxychloroquine] and chloroquine in the treatment of COVID-19 was revoked on 15 June 2020.[L14312]** Chloroquine was granted FDA Approval on 31 October 1949.[L12054]
Synonyms
  • Chloroquine phosphate
  • N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine
  • Chloroquinum
  • Chloroquine
  • Chlorochin
Brand Names
  • Aralen
  • Chloroquine Phosphate
  • Chloroquine
  • Chloroquine phosphate
  • Teva-chloroquine
IndicationChloroquine is indicated to treat infections of _P. vivax_, _P. malariae_, _P. ovale_, and susceptible strains of _P. falciparum_.[L12051] It is also used to treat extraintestinal amebiasis.[L12051] Chloroquine is also used off label for the treatment of rheumatic diseases,[A191655] as well as treatment and prophylaxis of Zika virus.[A191649,A191652] Chloroquine is currently undergoing clinical trials for the treatment of COVID-19.[A191631]
Categories
  • Agents Causing Muscle Toxicity
  • Agents that produce neuromuscular block (indirect)
  • Agents that reduce seizure threshold
  • alpha-Galactosidase, antagonists & inhibitors
  • Amebicides
ATC-Code
  • P01BB52
  • P01BA01
CAS number54-05-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Glutathione S-transferase A2MAEKPKLHYSNIRGRMESIRWLLAAAGVEFEEKFIKSAEDLDKLRNDGYL...unknowninhibitor
Tumor necrosis factorMSTESMIRDVELAEEALPKKTGGPQGSRRCLFLSLFSFLIVAGATTLFCL...unknowninhibitor
Toll-like receptor 9MGFCRSALHPLSLLVQAIMLAMTLALGTLPAFLPCELQPHGLVNCNWLFL...unknowninhibitor
Glutathione S-transferaseMGDNIVLYYFDARGKAELIRLIFAYLGIEYTDKRFGVNGDAFVEFKNFKK...unknowninhibitor
High mobility group protein B1MGKGDPKKPRGKMSSYAFFVQTCREEHKKKHPDASVNFSEFSKKCSERWK...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 444810
ChEMBL CHEMBL252715
ChEBI CHEBI:48811
CCDC/CSD GEXXAI, HOJLOI