(-)-pentazocine   

GtoPdb Ligand ID: 1606

Synonyms: pentazocine | WIN-20228
(-)-pentazocine is an approved drug (FDA (1967))
Compound class: Synthetic organic
Comment: (-)-pentazocine is one of the two enantiomers in the approved drug pentazocine. (-)-pentazocine is a κ-opioid receptor agonist, while (+)-pentazocine exhibits ten-fold greater affinity for the σ receptor. Pentazocine is a mixed agonist-antagonist opioid pain medication. It is postulated that pentazocine behaves as an agonist at the κ and σ opioid receptors and has weak antagonistic action at the μ receptor.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 23.47
Molecular weight 285.21
XLogP 3.69
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CC(=CCN1CCC2(C(C1Cc1c2cc(cc1)O)C)C)C
Isomeric SMILES CC(=CCN1CC[C@@]2([C@H]([C@H]1Cc1c2cc(cc1)O)C)C)C
InChI InChI=1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3/t14-,18+,19+/m0/s1
InChI Key VOKSWYLNZZRQPF-GDIGMMSISA-N
No information available.
Summary of Clinical Use
Pentazocine is used to treat moderate to severe pain. It is also used as part of surgical anesthesia.
Mechanism Of Action and Pharmacodynamic Effects
Evidence suggests that pentazocine antagonizes the opioid effects by competing for the same receptor sites.