Hydroxychloroquine sulfateProduct ingredient for Hydroxychloroquine

Name
Hydroxychloroquine sulfate
Drug Entry
Hydroxychloroquine

Hydroxychloroquine is a racemic mixture consisting of an R and S enantiomer.2 Hydroxychloroquine is an aminoquinoline like chloroquine.13 It is a commonly prescribed medication in the treatment of uncomplicated malaria, rheumatoid arthritis, chronic discoid lupus erythematosus, and systemic lupus erythematosus.13 Hydroxychloroquine is also used for the prophylaxis of malaria in regions where chloroquine resistance is unlikely.13 It was developed during World War II as a derivative of quinacrine with less severe side effects.6 Chloroquine and hydroxychloroquine are both being investigated for the treatment of SARS-CoV-2.7

The FDA emergency use authorization for hydroxychloroquine and chloroquine in the treatment of COVID-19 was revoked on 15 June 2020.14

Hydroxychloroquine was granted FDA approval on 18 April 1955.13

A recent study reported a fatality in the group being treated with hydroxychloroquine for COVID-19.10

Accession Number
DBSALT000096
Structure
Thumb
Synonyms
Not Available
UNII
8Q2869CNVH
CAS Number
747-36-4
Weight
Average: 433.95
Monoisotopic: 433.143819418
Chemical Formula
C18H28ClN3O5S
InChI Key
JCBIVZZPXRZKTI-UHFFFAOYSA-N
InChI
InChI=1S/C18H26ClN3O.H2O4S/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18;1-5(2,3)4/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21);(H2,1,2,3,4)
IUPAC Name
2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol; sulfuric acid
SMILES
OS(O)(=O)=O.CCN(CCO)CCCC(C)NC1=C2C=CC(Cl)=CC2=NC=C1
PubChem Compound
12947
ChemSpider
12410
ChEBI
629987
ChEMBL
CHEMBL1690
Wikipedia
Hydroxychloroquine
Predicted Properties
PropertyValueSource
Water Solubility0.0261 mg/mLALOGPS
logP3.87ALOGPS
logP2.89ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)15.59ChemAxon
pKa (Strongest Basic)9.76ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area48.39 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity97.97 m3·mol-1ChemAxon
Polarizability38.28 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon