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

General Information of Drug (ID: DR1264)
Drug Name
Perphenazine
Synonyms
Perfenazina; Perfenazina [INN-Spanish]; Perfenazina [Italian]; Perfenazine; Perphenan; Perphenazin; Perphenazinum; Perphenazinum [INN-Latin]; Perphenazine dimaleate; LS-112191; Perphenazine maleate; Perphenazine maleate (JP17); Perphenazine maleate [JAN]; (Z)-but-2-enedioic acid; 1-Piperazineethanol, 4-(3-(2-chlorophenothiazin-10-yl)propyl)-, maleate; 2-[4-[3-(2-chlorophenothiazin-10-yl)propyl]piperazin-1-yl]ethanol; 5352-90-9; 7K96LZ09JI; AC1O60XO; C13540; D02037; UNII-7K96LZ09JI; Sch 3940; Thilatazin; Tranquisan; Trifaron; Trilafon; Trilifan; Triphenot; perphenazine; 2-(4-(3-(2-Chloro-10H-phenothiazin-10-yl)propyl)piperazin-1-yl)ethanol; 4-[3-(2-Chlorophenothiazin-10-yl)propyl]-1-piperazineethanol; 58-39-9; C21H26ClN3OS; F-mon; NSC 150866; PZC; UNII-FTA7XXY4EZ; Chlorperphenazine; Chlorpiprazine; Decentan; Emesinal; Etaperazin; Etaperazine; Ethaperazine; Fentazin
Indication Schizophrenia [ICD11: 6A20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 404 Topological Polar Surface Area 55.2
Heavy Atom Count 27 Rotatable Bond Count 6
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
4748
PubChem SID
9631 ; 431795 ; 597373 ; 856006 ; 7703589 ; 7847569 ; 7980283 ; 8150080 ; 8152914 ; 10321518 ; 10528270 ; 10589046 ; 11111645 ; 11111646 ; 11336055 ; 11361294 ; 11364504 ; 11367066 ; 11369628 ; 11371696 ; 11374583 ; 11377790 ; 11462266 ; 11466153 ; 11467273 ; 11485339 ; 11485845 ; 11489418 ; 11490574 ; 11492658 ; 11495424 ; 12013414 ; 14903848 ; 17405488 ; 24262990 ; 24278642 ; 24362495 ; 24434791 ; 25676887 ; 26612555 ; 26680605 ; 26747080 ; 26747081 ; 29223834 ; 46507058 ; 47216833 ; 47291190 ; 47440321 ; 47440322 ; 47662342
ChEBI ID
ChEBI:8028
CAS Number
58-39-9
TTD Drug ID
D02HED
Formula
C21H26ClN3OS
Canonical SMILES
C1CN(CCN1CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)Cl)CCO
InChI
1S/C21H26ClN3OS/c22-17-6-7-21-19(16-17)25(18-4-1-2-5-20(18)27-21)9-3-8-23-10-12-24(13-11-23)14-15-26/h1-2,4-7,16,26H,3,8-15H2
InChIKey
RGCVKNLCSQQDEP-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
Hydroxychlorpromazine DM001825
16414
Oxidation - Hydroxylation 1 [5]
N-Dealkylated perphenazine DM001222 N. A. Oxidation - N-Dealkylation 1 [6]
Perphenazine sulfoxide DM001224
82341
Oxidation - S-Oxidation 1 [7]
Thioridazine 2-sulfoxide DM003069
4078
Unclear 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002005 Perphenazine N-Dealkylated perphenazine Oxidation - N-Dealkylation CYP1A2 ... [6]
MR002006 Perphenazine Perphenazine sulfoxide Oxidation - S-Oxidation CYP2D6 [7]
MR002007 Perphenazine Hydroxychlorpromazine Oxidation - Hydroxylation Unclear [5]
MR002008 Perphenazine Mesoridazine Unclear Unclear [5]
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 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[3]
⏷ Show the Full List of 7  DME(s)
References
1 Perphenazine Maleate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effect of antipsychotic drugs on human liver cytochrome P-450 (CYP) isoforms in vitro: preferential inhibition of CYP2D6. Drug Metab Dispos. 1999 Sep;27(9):1078-84.
3 Identification of the human cytochrome P450 isoforms mediating in vitro N-dealkylation of perphenazine. Br J Clin Pharmacol. 2000 Dec;50(6):563-71.
4 Use of antidepressant drugs in schizophrenic patients with depression. Encephale. 2006 Mar-Apr;32(2 Pt 1):263-9.
5 American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2511
6 Anti-Parkinson's disease drugs and pharmacogenetic considerations Expert Opin Drug Metab Toxicol. 2013 Jul;9(7):859-74. doi: 10.1517/17425255.2013.789018.
7 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.

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