Chloroquine phosphateProduct ingredient for Chloroquine

Show full entry for Chloroquine
Name
Chloroquine phosphate
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The FDA emergency use authorization for hydroxychloroquine and chloroquine in the treatment of COVID-19 was revoked on 15 June 2020.21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

See full entry for Chloroquine
Accession Number
DBSALT000025  (DBSALT001189)
Structure
Similar Structures
Synonyms
Chloroquine diphosphate
UNII
7FY24HE2G3
CAS Number
50-63-5
Weight
Average: 417.867
Monoisotopic: 417.15842065
Chemical Formula
C18H29ClN3O4P
InChI Key
AEUAEICGCMSYCQ-UHFFFAOYSA-N
InChI
InChI=1S/C18H26ClN3.H3O4P/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18;1-5(2,3)4/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21);(H3,1,2,3,4)
IUPAC Name
7-chloro-N-[5-(diethylamino)pentan-2-yl]quinolin-4-amine; phosphoric acid
SMILES
OP(O)(O)=O.CCN(CC)CCCC(C)NC1=CC=NC2=CC(Cl)=CC=C12
PubChem Compound
83818
ChemSpider
75637
ChEBI
370724
ChEMBL
CHEMBL1326
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