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

General Information of Drug (ID: DR1272)
Drug Name
Phenelzine
Synonyms
Phenalzine; Phenelzine; Phenelzine [INN:BAN]; Phenelzinum; Phenelzinum [INN-Latin]; Phenethyl-hydrazine; Phenethylhydrazine; Phenylethylhydrazine; Stinerval; W 1544-A; beta-Phenylethylhydrazine; phenethyl hydrazine; (2-phenylethyl)hydrazine; Fenelzin; Fenelzina; Fenelzina [INN-Spanish]; Fenelzyna; Fenelzyna [Polish]; Fenelzyne; Fenelzyne [Polish]; HYDRAZINE, PHENETHYL-; Hydrazine, (2-phenylethyl)-; Nardil; 1-Hydrazino-2-phenylethane; 2-Phenethylhydrazine; 2-Phenylethylhydrazine; 51-71-8; EINECS 200-117-9; UNII-O408N561GF; W1544
Indication Depression [ICD11: 6A71] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 136.19 Topological Polar Surface Area 38
Heavy Atom Count 10 Rotatable Bond Count 3
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
3675
PubChem SID
9634 ; 5152742 ; 8152321 ; 10524963 ; 11111653 ; 11111654 ; 11335237 ; 11360476 ; 11363745 ; 11364679 ; 11366307 ; 11367241 ; 11368869 ; 11369803 ; 11371693 ; 11372844 ; 11374089 ; 11375403 ; 11377031 ; 11377966 ; 11461448 ; 11466198 ; 11467318 ; 11484873 ; 11485696 ; 11488825 ; 11490493 ; 11492290 ; 11494665 ; 15297289 ; 29222798 ; 46507348 ; 47291290 ; 47365378 ; 47440429 ; 47440430 ; 47515488 ; 47589153 ; 47589154 ; 47662481 ; 47885575 ; 48334681 ; 49698876 ; 49977970 ; 50111200 ; 53787015 ; 57321933 ; 74503885 ; 85789353 ; 90341694
ChEBI ID
CHEBI:8060
CAS Number
51-71-8
TTD Drug ID
D0P9AC
Formula
C8H12N2
Canonical SMILES
C1=CC=C(C=C1)CCNN
InChI
1S/C8H12N2/c9-10-7-6-8-4-2-1-3-5-8/h1-5,10H,6-7,9H2
InChIKey
RMUCZJUITONUFY-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
4- hydroxyphenelzine DM001230
129667
Oxidation - 4-Hydroxylation 1 [3]
Phenethylamine DM001227
1001
Hydrolysis - Hydrolysis 1 [3]
Phenyl acetic acid DM001228
999
Hydrolysis - Hydrolysis 1 [3]
(4-Hydroxyphenyl) acetic acid DM001229
127
Hydrolysis - Hydrolysis 2 [3]
(4-Hydroxyphenyl) acetic acid DM001229
127
Oxidation - 4-Hydroxylation 2 [3]
Phenyl acetic acid DM001228
999
Unclear 2 [3]
(4-Hydroxyphenyl) acetic acid DM001229
127
Oxidation - 4-Hydroxylation 3 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002018 Phenelzine Phenethylamine Hydrolysis - Hydrolysis CYP3A4 ... [3]
MR002019 Phenelzine Phenylacetic acid Hydrolysis - Hydrolysis Unclear [3]
MR002020 Phenelzine 4- hydroxyphenelzine Oxidation - 4-Hydroxylation Unclear [3]
MR002017 4- hydroxyphenelzine 4-hydroxyphenylacetic acid Hydrolysis - Hydrolysis Unclear [3]
MR002015 Phenethylamine Phenylacetic acid Unclear Unclear [3]
MR002016 Phenylacetic acid 4-hydroxyphenylacetic acid Oxidation - 4-Hydroxylation Unclear [3]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
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]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Phenelzine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 An evaluation of potential mechanism-based inactivation of human drug metabolizing cytochromes P450 by monoamine oxidase inhibitors, including isoniazid. Br J Clin Pharmacol. 2006 May;61(5):570-84.
3 Insights into the mechanisms of action of the MAO inhibitors phenelzine and tranylcypromine: a review J Psychiatry Neurosci. 1992 Nov;17(5):206-14.

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