(-)-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
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
μ receptor Hs Agonist Partial agonist 8.4 pKi - 1
pKi 8.4 [1]
κ receptor Hs Agonist Partial agonist 7.8 – 8.6 pKi - 1-2
pKi 7.8 – 8.6 [1-2]
δ receptor Hs Agonist Full agonist 7.3 pKi - 1
pKi 7.3 [1]
Selectivity at other protein targets
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
sigma non-opioid intracellular receptor 1 Hs Antagonist Antagonist - - -
Ligand mentioned in the following text fields