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

General Information of Drug (ID: DR5206)
Drug Name
Selegiline
Synonyms
selegiline; L-Deprenalin; Emsam; (-)-selegiline; Selegilinum; Selegilina; Carbex; 14611-51-9; Selegilinum [INN-Latin]; Selegilina [INN-Spanish]; UNII-2K1V7GP655; l-E 250; CHEMBL972; CHEBI:9086; N-methyl-N-[(2R)-1-phenylpropan-2-yl]prop-2-yn-1-amine; 2K1V7GP655; (R)-(-)-N,alpha-Dimethyl-N-2-propinylphenethylamine; Benzeneethanamine, N,alpha-dimethyl-N-2-propynyl-, (R)-; selgene; (R)-(-)-N-Methyl-N-(1-phenyl-2-propyl)-2-propinylamin; Selegyline; Zalapar; Selegiline (transdermal, Parkinson's/depression); Zunrisa/Rezonic
Indication Major depressive disorder [ICD11: 6A70-6A7Z] Approved [1]
Chemotherapy-induced nausea [ICD11: ICD11: MD90] Discontinued in Phase 3 [2]
Skin imperfections [ICD11: ICD11: EK71] Patented [3]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 187.28 Topological Polar Surface Area 3.2
Heavy Atom Count 14 Rotatable Bond Count 4
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
26757
ChEBI ID
CHEBI:9086
CAS Number
14611-51-9
TTD Drug ID
D0S2UG
Formula
C13H17N
Canonical SMILES
C[C@H](CC1=CC=CC=C1)N(C)CC#C
InChI
InChI=1S/C13H17N/c1-4-10-14(3)12(2)11-13-8-6-5-7-9-13/h1,5-9,12H,10-11H2,2-3H3/t12-/m1/s1
InChIKey
MEZLKOACVSPNER-GFCCVEGCSA-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
Desmethyl selegiline DM001288
200718
Unclear - Unclear 1 [5]
MethAmphetamine DM005397
10836
Unclear - Unclear 1 [5]
Amphetamine DM003887
3007
Unclear - Unclear 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010841 Selegiline Methamphetamine Unclear - Unclear Unclear [5]
MR010843 Selegiline Desmethyl selegiline Unclear - Unclear Unclear [5]
MR010844 Desmethyl selegiline Amphetamine Unclear - Unclear CYP2B6 ... [5]
MR010842 Methamphetamine Amphetamine Unclear - Unclear CYP2D6 [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
[4]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[5]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[5]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[4]
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]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
⏷ Show the Full List of 7  DME(s)
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6639).
2 Clinical pipeline report, company report or official report of GlaxoSmithKline.
3 Novel monoamine oxidase inhibitors: a patent review (2012 - 2014).Expert Opin Ther Pat. 2015 Jan;25(1):91-110.
4 Comparative studies on the cytochrome p450-associated metabolism and interaction potential of selegiline between human liver-derived in vitro systems. Drug Metab Dispos. 2003 Sep;31(9):1093-102.
5 Physiologically Based Pharmacokinetic Modeling of Transdermal Selegiline and Its Metabolites for the Evaluation of Disposition Differences between Healthy and Special Populations

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