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

General Information of Drug (ID: DR0308)
Drug Name
Chlorpromazine hydrochloride
Synonyms
Aminazin monohydrochloride; Aminazinum; Ampliactil monohydrochloride; Chloractil; Chloropromazine monohydrochloride; Chlorpromazine Hcl; Chlorpromazine hydrochloride; Chlorpromazine monohydrochloride; Chlorpromazine; Chlorpromazinium chloride; Contomin hydrochloride; Fenactil monohydrochloride; Hebanil; Hibanil; Hibernal; Hybernal; Klorproman; Klorpromex; Lomazine; Marazine; Megaphen hydrochloride; Megatil; Neurazine; Norcozine; Plegomazin; Promachel; Promacid; Promapar; Promexin; Sonazine; Taroctyl; Tranzine; Unitensen; Chlor-Promanyl; Chlorderazin; Chloropromazine; Chlorpromados; Chlorpromazin; Chlorpromazinum; Clorpromazina; Contomin; Cromedazine; Elmarin; Esmind; Fenactil; Fenaktyl; Fraction AB; Largactil; Largactilothiazine; Largactyl; Megaphen; Novomazina; Phenactyl; Plegomasine; Proma; Promactil; Promazil; Prozil; Psychozine; SKF 2601-A; Sanopron; Thorazine; Torazina; Wintermin; chlorpromazine; 2-Chloropromazine; 3-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethylpropan-1-amine; 50-53-3; Aminasine; Aminazin; Aminazine; Ampliactil; Amplictil; 69-09-0
Indication Schizophrenia [ICD11: 6A20] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 355.3 Topological Polar Surface Area 31.8
Heavy Atom Count 22 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
6240
ChEBI ID
CHEBI:3649
CAS Number
69-09-0
TTD Drug ID
D01ZII
Formula
C17H20Cl2N2S
Canonical SMILES
CN(C)CCCN1C2=CC=CC=C2SC3=C1C=C(C=C3)Cl.Cl
InChI
1S/C17H19ClN2S.ClH/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;1H
InChIKey
FBSMERQALIEGJT-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 1 [6]
Demonomethylchlorpromazine DM001823
62875
Unclear 1 [6] , [7]
Hydroxychlorpromazine DM001825
16414
Oxidation - 7-Hydroxylation 1 [6] , [7]
Opromazine DM001827
70413
Unclear 1 [6] , [7]
Dedimethylchlorpromazine DM001824
74981
Unclear 2 [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000642 Chlorpromazine hydrochloride Demonomethylchlorpromazine Unclear CYP3A4 ... [6], [7]
MR000643 Chlorpromazine hydrochloride Hydroxychlorpromazine Oxidation - 7-Hydroxylation CYP1A2 ... [6], [7]
MR000644 Chlorpromazine hydrochloride Chlorpromazine-N-oxide Unclear Unclear [6]
MR000645 Chlorpromazine hydrochloride Opromazine Unclear CYP3A4 ... [6], [7]
MR000641 Demonomethylchlorpromazine Dedimethylchlorpromazine Unclear 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
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Docosahexaenoic acid omega-hydroxylase (CYP4F11) DME0616 Homo sapiens
CP4FB_HUMAN
1.14.14.1
[5]
References
1 Chlorpromazine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Functional polymorphisms of the cytochrome P450 1A2 (CYP1A2) gene and prolonged QTc interval in schizophrenia. Prog Neuropsychopharmacol Biol Psychiatry. 2007 Aug 15;31(6):1297-302.
3 Use of antidepressant drugs in schizophrenic patients with depression. Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9.
4 Effect of classic and atypical neuroleptics on cytochrome P450 3A (CYP3A) in rat liver. Pharmacol Rep. 2012;64(6):1411-8.
5 Expression and characterization of human cytochrome P450 4F11: putative role in the metabolism of therapeutic drugs and eicosanoids. Toxicol Appl Pharmacol. 2004 Sep 15;199(3):295-304.
6 Classics in Chemical Neuroscience: Chlorpromazine ACS Chem Neurosci. 2019 Jan 16;10(1):79-88. doi: 10.1021/acschemneuro.8b00258.
7 Determination of chlorpromazine and its metabolites in animal-derived foods using QuEChERS-based extraction, EMR-Lipid cleanup, and UHPLC-Q-Orbitrap MS analysis. Food Chem. 2023 Mar 1;403:134298. doi: 10.1016/j.foodchem.2022.134298.

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