Chloroquine hydrochlorideProduct ingredient for Chloroquine

Name
Chloroquine hydrochloride
Drug Entry
Chloroquine

Chloroquine is an aminoquinolone derivative first developed in the 1940s for the treatment of malaria.4 It was the drug of choice to treat malaria until the development of newer antimalarials such as pyrimethamine, artemisinin, and mefloquine.17 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.18

The FDA emergency use authorization for hydroxychloroquine and chloroquine in the treatment of COVID-19 was revoked on 15 June 2020.21

Chloroquine was granted FDA Approval on 31 October 1949.20

Accession Number
DBSALT001317
Structure
Thumb
Synonyms
Chloroquine HCl
UNII
NT0J0815S5
CAS Number
3545-67-3
Weight
Average: 392.79
Monoisotopic: 391.134881
Chemical Formula
C18H28Cl3N3
InChI Key
PCFGECQRSMVKCC-UHFFFAOYSA-N
InChI
InChI=1S/C18H26ClN3.2ClH/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);2*1H
IUPAC Name
7-chloro-N-[5-(diethylamino)pentan-2-yl]quinolin-4-amine dihydrochloride
SMILES
Cl.Cl.CCN(CC)CCCC(C)NC1=CC=NC2=CC(Cl)=CC=C12
ChemSpider
75639
Wikipedia
Chloroquine
Predicted Properties
PropertyValueSource
Water Solubility0.0175 mg/mLALOGPS
logP5.28ALOGPS
logP3.93ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)10.32ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.16 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity96.42 m3·mol-1ChemAxon
Polarizability37.29 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon