dextropropoxyphene   Click here for help

GtoPdb Ligand ID: 7593

Synonyms: (+)-alpha-propoxyphene | Darvon® | propoxyphene
Approved drug
dextropropoxyphene is an approved drug
Compound class: Synthetic organic
Comment: Dextropropoxyphene is principally an opioid analgesic. Chemically it is an optical isomer of levopropoxyphene (the (2R,3S) optical isomer with PubChem CID 200742); dextropropoxyphene being the (2S,3R) enantiomer. Marketing in Europe and the US has been discontinued due to concerns of fatal overdoses and heart arrhythmias.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 9
Topological polar surface area 29.54
Molecular weight 339.22
XLogP 4.37
No. Lipinski's rules broken 0
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Canonical SMILES CCC(=O)OC(c1ccccc1)(C(CN(C)C)C)Cc1ccccc1
Isomeric SMILES CCC(=O)O[C@](c1ccccc1)([C@@H](CN(C)C)C)Cc1ccccc1
InChI InChI=1S/C22H29NO2/c1-5-21(24)25-22(18(2)17-23(3)4,20-14-10-7-11-15-20)16-19-12-8-6-9-13-19/h6-15,18H,5,16-17H2,1-4H3/t18-,22+/m1/s1
1. Xiao Y, Smith RD, Caruso FS, Kellar KJ. (2001)
Blockade of rat alpha3beta4 nicotinic receptor function by methadone, its metabolites, and structural analogs.
J. Pharmacol. Exp. Ther., 299 (1): 366-71. [PMID:11561100]