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

General Information of Drug (ID: DR3387)
Drug Name
Chlorpromazine
Synonyms
Aminasine; Aminazin; Aminazine; Ampliactil; Amplicitil; Amplictil; BC 135; Chlor-PZ; Chlor-Promanyl; Chlordelazine; Chlorderazin; Chloropromazine; Chlorpromados; Chlorpromanyl (discontinued); Chlorpromazin; Chlorpromazine (USP/INN); Chlorpromazine Tannate; Chlorpromazine [USAN:INN:BAN]; Chlorpromazinum; Chlorpromazinum [INN-Latin]; Clorpromazina; Clorpromazina [INN-Spanish]; Clorpromazina [Italian]; Contomin; Cromedazine; Elmarin; Esmind; Fenactil; Fenaktyl; Fraction AB; HL 5746; JHICC02042; Largactil; Largactil (TN); Largactil Liquid; Largactil Oral Drops; Largactilothiazine; Largactyl; Megaphen; Novo-Chlorpromazine; Novomazina; Phenactyl; Phenathyl; Phenothiazine hydrochloride; Plegomasine; Plegomazin; Prazilpromactil; Proma; Promactil; Promazil; Propaphen; Propaphenin; Prozil; Psychozine; SKF 2601-A; SKF 2601A; SKF-2601; Sanopron; Thorazine; Thorazine (TN); Thorazine Spansule; Thorazine Suppositories; Thorazine hydrochloride; Torazina; Wintermin; Z80
Indication Coronavirus Disease 2019 (COVID-19) [ICD11: 1D6Y] Phase 3 [1]
Schizophrenia [ICD11: ICD11: 6A20] Withdrawn from market [2]
Middle East Respiratory Syndrome (MERS) [ICD11: ICD11: 1D64] Investigative [3]
Severe acute respiratory syndrome (SARS) [ICD11: ICD11: 1D65] Investigative [4]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 318.9 Topological Polar Surface Area 31.8
Heavy Atom Count 21 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
2726
ChEBI ID
CHEBI:3647
CAS Number
34468-21-8
TTD Drug ID
D0V6GN
Formula
C17H19ClN2S
Canonical SMILES
CN(C)CCCN1C2=CC=CC=C2SC3=C1C=C(C=C3)Cl
InChI
InChI=1S/C17H19ClN2S/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20/h3-4,6-9,12H,5,10-11H2,1-2H3
InChIKey
ZPEIMTDSQAKGNT-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
Chlorpromazine-N-oxide DM001826
443037
Unclear - Unclear 1 [5]
Dedimethylchlorpromazine DM001824
74981
Unclear - Unclear 1 [5]
Demonomethylchlorpromazine DM001823
62875
Unclear - Unclear 1 [5]
Hydroxychlorpromazine DM001825
16414
Oxidation - 7-hydroxylation 1 [5]
Opromazine DM001827
70413
Oxidation - S-oxidation 1 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR011380 Chlorpromazine Hydroxychlorpromazine Oxidation - 7-hydroxylation CYP2D6 [5]
MR011381 Chlorpromazine Chlorpromazine-N-oxide Unclear - Unclear Unclear [5]
MR011382 Chlorpromazine Dedimethylchlorpromazine Unclear - Unclear Unclear [5]
MR011383 Chlorpromazine Demonomethylchlorpromazine Unclear - Unclear Unclear [5]
MR011384 Chlorpromazine Opromazine Oxidation - S-oxidation CYP3A4 [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[5]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
References
1 ClinicalTrials.gov (NCT04366739) Repurposing of Chlorpromazine in Covid-19 Treatment. U.S. National Institutes of Health.
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 Coronaviruses - drug discovery and therapeutic options. Nat Rev Drug Discov. 2016 May;15(5):327-47.
4 Coronaviruses - drug discovery and therapeutic options. Nat Rev Drug Discov. 2016 May;15(5):327-47.
5 DrugBank(Pharmacology-Metabolism):Chlorpromazine
6 Cytochrome P450 inactivation by pharmaceuticals and phytochemicals: therapeutic relevance Drug Metab Rev. 2008;40(1):101-47. doi: 10.1080/03602530701836704.

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