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

General Information of Drug (ID: DR5230)
Drug Name
Levomethadyl Acetate
Synonyms
LAAM; Levacetilmetadol; Levacetylmethadol; Levacetylmethadolum; Levomethadyl; Orlaam; Levacetylmethadol [INN]; Levacetilmetadol [INN-Spanish]; Levacetylmethadol (INN); Levacetylmethadolum [INN-Latin]; Levo-Alphacetylmethadol; Levo-Methadyl acetate; Levomethadyl acetate (USAN); Orlaam (TN); A-l-acetylmethadol; Alpha-l-Acetylmethadol; L-alpha-Acetylmethadol; Levo-alpha-Acetylmethadol; N-alpha-Acetylmethadol; Alpha-(-)-Acetylmethadol; [(3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-3-yl] acetate; [S-(R*,R*)]-beta-[2-Dimethylamino)propyl]-alpha-ethyl-beta-phenylbenzeneethanol acetate (ester); Benzeneethanol, beta-[(2S)-2-(dimethylamino)propyl]-alpha-ethyl-beta-phenyl-, acetate (ester), (alphaS)-(9CI); (-)-alpha-Acetylmethadol; (1S,4S)-4-(dimethylamino)-1-ethyl-2,2-diphenylpentyl acetate; (3S,6S)-6-(dimethylamino)-4,4-diphenylheptan-2-yl acetate; 1-alpha-Acetylmethadol; 3-Heptanol, 6-(dimethylamino)-4,4-diphenyl-, acetate (ester), (3S,6S)-(-)-(8CI)
Indication Opiate dependence [ICD11: 6C43] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 353.5 Topological Polar Surface Area 29.5
Heavy Atom Count 26 Rotatable Bond Count 9
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
15130
ChEBI ID
CHEBI:6441
CAS Number
1477-40-3
TTD Drug ID
D05PIZ
Formula
C23H31NO2
Canonical SMILES
CC[C@@H](C(C[C@H](C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C
InChI
InChI=1S/C23H31NO2/c1-6-22(26-19(3)25)23(17-18(2)24(4)5,20-13-9-7-10-14-20)21-15-11-8-12-16-21/h7-16,18,22H,6,17H2,1-5H3/t18-,22-/m0/s1
InChIKey
XBMIVRRWGCYBTQ-AVRDEDQJSA-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
Nor-levomethadyl acetate (nor-LAAM) DM017050 N. A. Oxidation - N-demethylation 1 [4] , [2]
Noracymethadol DM000299
15129
Oxidation - N-demethylation 1 [3]
Dinor-levomethadyl acetate DM000300
170384
Unclear - Unclear 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR008028 Levomethadyl Acetate Nor-levomethadyl acetate (nor-LAAM) Oxidation - N-demethylation CYP3A4 ... [4], [2]
MR008030 Levomethadyl Acetate Noracymethadol Oxidation - N-demethylation CYP3A4 [3]
MR008029 Nor-levomethadyl acetate (nor-LAAM) Dinor-levomethadyl acetate Unclear - Unclear CYP3A7 [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[2]
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: 7212).
2 Differential N-demethylation of l-alpha-acetylmethadol (LAAM) and norLAAM by cytochrome P450s 2B6, 2C18, and 3A4
3 DrugBank(Pharmacology-Metabolism):Levomethadyl Acetate
4 The KEGG resource for deciphering the genome

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