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

General Information of Drug (ID: DR3396)
Drug Name
Hydroxychloroquine
Synonyms
Hidroxicloroquina; Hidroxicloroquina [INN-Spanish]; Hydroxychlorochin; Gen-Hydroxychloroquine 200mg Tablets; HCQ; Hydroxychloroguine; Hydroxychloroquine (INN);Hydroxychloroquine [INN:BAN]; Hydroxychloroquine Sulfate (1:1) Salt; Hydroxychloroquinum; Hydroxychloroquinum [INN-Latin]; Idrossiclorochina; Idrossiclorochina [DCIT]; Oxichlorochinum; Oxichloroquine; Oxychlorochin; Oxychloroquine; Plaquenil (TN); Polirreumin; Polirreumin (TN); Quensyl; WIN 1258
Indication Malaria [ICD11: 1F40-1F45] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 335.9 Topological Polar Surface Area 48.4
Heavy Atom Count 23 Rotatable Bond Count 9
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
3652
ChEBI ID
CHEBI:5801
CAS Number
118-42-3
TTD Drug ID
D0UK3A
Formula
C18H26ClN3O
Canonical SMILES
CCN(CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl)CCO
InChI
InChI=1S/C18H26ClN3O/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/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21)
InChIKey
XXSMGPRMXLTPCZ-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
Bidesethylchloroquine DM004782
122672
Unclear - Unclear 1 [3]
Desethylchloroquine DM004780
95478
Unclear - Unclear 1 [4] , [2]
Desethylhydroxychloroquine DM004781
71826
Unclear - Unclear 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012185 Hydroxychloroquine Monodesethylchloroquine Unclear - Unclear CYP3A5 ... [4], [2]
MR012186 Hydroxychloroquine Desethylhydroxychloroquine Unclear - Unclear Unclear [3]
MR012187 Hydroxychloroquine Bisdesethylchloroquine Unclear - Unclear Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7198).
2 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.
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 The single dose kinetics of chloroquine and its major metabolite desethylchloroquine in healthy subjects

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