General Information of Drug (ID: DR0944)
Drug Name
Levomethadyl acetate hydrochloride
Synonyms
Levacetilmetadol; Levacetilmetadol [INN-Spanish]; Levacetylmethadol; Levacetylmethadol (INN); Levacetylmethadol [INN]; Levacetylmethadolum; Levacetylmethadolum [INN-Latin]; Levomethadyl; Levomethadyl acetate; Levacetyl methadol hydrochloride; LAAM hydrochloride; Levomethadyl acetate HCl; MK 790; MK-790 hydrochloride; ORLAAM hydrochloride; l-Acetylmethadol hydrochloride; (-)-(3S,6S)-6-(Dimethylamino)-4,4-diphenyl-3-heptanol acetate (ester), hydrochloride; 43033-72-3; 6-Dimethylamino-4,4-diphenyl-3-heptanolacetate.HCl; B54CW5KG52; CCRIS 3321; Levomethadyl acetate hydrochloride; Levomethadyl acetate hydrochloride [USAN]; UNII-B54CW5KG52; alpha-l-Acetylmethadol hydrochloride; l-alpha-Acetylmethadol hydrochloride; N-alpha-Acetylmethadol; Orlaam; alpha-l-Acetylmethadol; l-alpha-Acetylmethadol; levo-Alphacetylmethadol; levo-Methadyl acetate; levo-alpha-Acetylmethadol; (-)-alpha-Acetylmethadol; 1-alpha-Acetylmethadol; 1477-40-3; DEA No. 9648; LAAM; UNII-R3B637Y991; alpha-(-)-Acetylmethadol
Indication Opiate dependence [ICD11: 6C43] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 390 Topological Polar Surface Area 29.5
Heavy Atom Count 27 Rotatable Bond Count 9
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
39371
ChEBI ID
CHEBI:6442
CAS Number
43033-72-3
Formula
C23H32ClNO2
Canonical SMILES
CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)OC(=O)C.Cl
InChI
1S/C23H31NO2.ClH/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;1H/t18-,22-;/m0./s1
InChIKey
UXBPQRGCVJOTNT-COBSGTNCSA-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
Noracymethadol DM000299
15129
Oxidation - Demethylation 1 [3] , [2]
Unclear DM009999 N. A. Unclear 1 [5]
Dinor-levomethadyl acetate DM000300
170384
Oxidation - Demethylation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003113 Levomethadyl acetate hydrochloride NorLAAM Oxidation - Demethylation CYP3A4 [3], [2]
MR003114 Levomethadyl acetate hydrochloride . Unclear CYP3A5 [5]
MR003112 NorLAAM Dinor-levomethadyl acetate Oxidation - Demethylation CYP3A4 [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aromatase (CYP19A1) DME0002 Homo sapiens
CP19A_HUMAN
1.14.14.14
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
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 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[4]
⏷ Show the Full List of 12  DME(s)
References
1 Levomethadyl Acetate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 N-demethylation of levo-alpha-acetylmethadol by human placental aromatase. Biochem Pharmacol. 2004 Mar 1;67(5):885-92.
3 Paradoxical role of cytochrome P450 3A in the bioactivation and clinical effects of levo-alpha-acetylmethadol: importance of clinical investigations to validate in vitro drug metabolism studies. Clin Pharmacokinet. 2005;44(7):731-51.
4 Drug Interactions Flockhart Table
5 Drug Interactions Flockhart Table:Docetaxel

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