Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0837)
Drug Name
Hydroxychloroquine sulfate
Synonyms
Hydroxychloroquine sulfate [USP]; Hydroxychloroquine sulphate; Plaquinol; TCMDC-123987; Toremonil; 2-((4-((7-Chloroquinolin-4-yl)amino)pentyl)(ethyl)amino)ethanol sulfate; 747-36-4; AI3-52706; AK-72909; DSSTox_CID_27788; DSSTox_RID_82563; EINECS 212-019-3; Ethanol, 2-((4-((7-chloro-4-quinolinyl)amino)pentyl)ethylamino)-, sulfate (1:1) (salt); Ethanol, 2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)-, sulfate (1:1) (salt); NSC 4375; Ercoquin; HCQ sulfate; HYDROXYCHLOROQUINE SULFATE
Indication Malaria [ICD11: 1F40] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 434 Topological Polar Surface Area 131
Heavy Atom Count 28 Rotatable Bond Count 9
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
12947
CAS Number
747-36-4
TTD Drug ID
D0OJ4L
Formula
C18H28ClN3O5S
Canonical SMILES
CCN(CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl)CCO.OS(=O)(=O)O
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)
InChIKey
JCBIVZZPXRZKTI-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Desethylchloroquine DM004780
95478
Oxidation - N-dealkylation 1 [3] , [2] , [4]
Desethylhydroxychloroquine DM004781
71826
Oxidation - N-dealkylation 2 [3] , [2] , [4]
Bidesethylchloroquine DM004782
122672
Oxidation - N-dealkylation 3 [3] , [2] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005140 Hydroxychloroquine sulfate Desethylchloroquine Oxidation - N-dealkylation CYP3A4 [3], [2], [4]
MR005141 Hydroxychloroquine sulfate Desethylhydroxychloroquine Oxidation - N-dealkylation CYP3A4 [3], [2], [4]
MR005142 Hydroxychloroquine sulfate Bidesethylchloroquine Oxidation - N-dealkylation CYP3A4 [3], [2], [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Hydroxychloroquine Sulfate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Hydroxychloroquine: a physiologically-based pharmacokinetic model in the context of cancer-related autophagy modulation. J Pharmacol Exp Ther. 2018 Jun;365(3):447-459.
3 Pharmacokinetics of hydroxychloroquine and its clinical implications in chemoprophylaxis against malaria caused by Plasmodium vivax. Antimicrob Agents Chemother. 2009 Apr;53(4):1468-75.
4 Metabolism and Interactions of Chloroquine and Hydroxychloroquine with Human Cytochrome P450 Enzymes and Drug Transporters Curr Drug Metab. 2020;21(14):1127-1135. doi: 10.2174/1389200221999201208211537.

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