methadone   Click here for help

GtoPdb Ligand ID: 5458

Synonyms: (±)-methadone | dl-methadone | Dolophine HCL® | methadone HCl | Methadose®
Approved drug
methadone is an approved drug (FDA (1947, prior history not available))
Compound class: Synthetic organic
Comment: The approved drug methadone is a racemic mixture of two enantiomers; (S)-methadone and (R)-methadone. The structure shown here does not specify stereochemistry and represents the mixture.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 20.31
Molecular weight 309.21
XLogP 4.59
No. Lipinski's rules broken 0
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Canonical SMILES CCC(=O)C(c1ccccc1)(c1ccccc1)CC(N(C)C)C
Isomeric SMILES CCC(=O)C(c1ccccc1)(c1ccccc1)CC(N(C)C)C
InChI InChI=1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3
1. Poulain R, Horvath D, Bonnet B, Eckhoff C, Chapelain B, Bodinier MC, Déprez B. (2001)
From hit to lead. Combining two complementary methods for focused library design. Application to mu opiate ligands.
J Med Chem, 44 (21): 3378-90. [PMID:11585443]