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Compound Detail

CHEMBL1514

LEVOMETHADYL ACETATE
💊 Approved Drug
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💊 Approved Drug
CC[C@H](OC(C)=O)C(C[C@H](C)N(C)C)(c1ccccc1)c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1514
Name LEVOMETHADYL ACETATE
Phase Approved
Structure Type MOL
InChI Key XBMIVRRWGCYBTQ-AVRDEDQJSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL1201402

Known Names

LAA-M LAAM Levacetilmetadol Levacetylmethadol Levo-alphacetylmethadol Levoacetyl methadol Levomethadyl acetate Orlaam
1
Targets
1
Activities
1
Assay Types
5
PK Parameters
5
Publications
8
Known Names
2
Indications
1
Mechanisms

Molecular Properties

353.5
MW (Da)
4.65
ALogP
3
HBA
0
HBD
29.5
PSA (Ų)
0.65
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1993
Availability Withdrawn
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Withdrawn Natural Product Prodrug
USAN Year 1972

Extended Properties

Molecular Formula C23H31NO2
MW 353.51
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.13

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Mu opioid receptor agonist AGONIST Mu-type opioid receptor ✓ ✓

Indications

Opioid-Related Disorders Substance-Related Disorders

ATC Classification

N07BC03
levacetylmethadol
Level 1: NERVOUS SYSTEM
Level 2: OTHER NERVOUS SYSTEM DRUGS

Drug Warnings

Withdrawn
cardiotoxicity
adverse cardiac events
Country: European Union   Year: 2001

Activity Summary

IC50 1 meas. best 5.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.66 5.66 2187.8 1

Pharmacokinetic Data

Parameter Value Units Species
CL 5.4 mL.min-1.kg-1 Homo sapiens
F 47.0 % Homo sapiens
Fu 0.2 - Homo sapiens
MRT 26.0 hr Homo sapiens
T1/2 18.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 2187.76 nM 5.66 Inhibitory concentration against potassium channel HERG 15911273

Literature References

PubMed DOI Target Context # Activities
18426954 10.1124/dmd.108.020479 ADMET 4
15911273 10.1016/j.bmcl.2005.03.080 Voltage-gated inwardly rectifying potassium channel KCNH2 1
17870541 10.1016/j.bmc.2007.08.060 Homo sapiens 1
18426954 10.1124/dmd.108.020479 NON-PROTEIN TARGET 1
20020916 10.1080/15376510701857262 Phospholipidosis 1

Data from ChEMBL 36 via Core Engine