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

General Information of Drug (ID: DR1258)
Drug Name
Perazine
Synonyms
Perazine maleate; LS-105593; SCHEMBL220704; (E)-but-2-enedioic acid; 10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine; 10H-Phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-, (Z)-2-butenedioate; AC1O6123; Phenothiazine, 10-(3-(4-methyl-1-piperazinyl)propyl)-, maleate
Indication Cerebrovascular dementia [ICD11: 6D81] Phase 4 [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 455.6 Topological Polar Surface Area 110
Heavy Atom Count 32 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 8
Cross-matching ID
PubChem CID
6444542
CAS Number
6002-77-3
TTD Drug ID
D07JWT
Formula
C24H29N3O4S
Canonical SMILES
CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=CC=CC=C42.C(=CC(=O)O)C(=O)O
InChI
1S/C20H25N3S/c1-21-13-15-22(16-14-21)11-6-12-23-17-7-2-4-9-19(17)24-20-10-5-3-8-18(20)23/h2-5,7-10H,6,11-16H2,1H3
InChIKey
UASWVXBJEDDYKU-WLHGVMLRSA-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
Hydroxyperazine DM002755 N. A. Unclear 1 [2]
N-desmethylperazine DM002752
151090
Oxidation - N-Demethylation 1 [2]
Perazine 5-sulfoxide metabolite DM002754
159893
Oxidation - Sulphoxidation 1 [2]
N-{3-(phenothiazinyl-10)-propyl}ethylenediamine DM002753
56621470
Oxidation - N-Dealkylation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001986 Perazine N-desmethylperazine Oxidation - N-Demethylation CYP3A4 ... [2]
MR001987 Perazine Perazine 5-sulfoxide metabolite Oxidation - Sulphoxidation CYP3A4 ... [2]
MR001988 Perazine Hydroxyperazine Unclear Unclear [2]
MR001985 N-desmethylperazine N-{3-(phenothiazinyl-10)-propyl}ethylenediamine Oxidation - N-Dealkylation CYP3A4 ... [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
⏷ Show the Full List of 8  DME(s)
References
1 Comparative risk of death in older adults treated with antipsychotics: a population-based cohort study. Eur Neuropsychopharmacol. 2016 Sep;26(9):1390-1400.
2 The metabolism of the piperazine-type phenothiazine neuroleptic perazine by the human cytochrome P-450 isoenzymes. Eur Neuropsychopharmacol. 2004 May;14(3):199-208.
3 Perazine as a potent inhibitor of human CYP1A2 but not CYP3A4. Pol J Pharmacol. 2002 Jul-Aug;54(4):407-10.
4 Cytochrome P-450 enzymes and FMO3 contribute to the disposition of the antipsychotic drug perazine in vitro. Psychopharmacology (Berl). 2000 Sep;151(4):312-20.
5 Effects of phenothiazine neuroleptics on the rate of caffeine demethylation and hydroxylation in the rat liver. Pol J Pharmacol. 2001 Nov-Dec;53(6):615-21.

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