(-)-pentazocine   Click here for help

GtoPdb Ligand ID: 1606

Synonyms: pentazocine | WIN-20228
Approved drug
(-)-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.
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: pentazocine

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1967))
International Nonproprietary Names Click here for help
INN number INN
1674 pentazocine
Synonyms Click here for help
pentazocine | WIN-20228
Database Links Click here for help
BindingDB Ligand 50001028
CAS Registry No. 359-83-1 (source: Scifinder)
ChEMBL Ligand CHEMBL560
DrugBank Ligand DB00652
GtoPdb PubChem SID 135650806
PubChem CID 441278
Search Google for chemical match using the InChIKey VOKSWYLNZZRQPF-GDIGMMSISA-N
Search Google for chemicals with the same backbone VOKSWYLNZZRQPF
Search PubMed clinical trials pentazocine
Search PubMed titles pentazocine
Search PubMed titles/abstracts pentazocine
Search UniChem for chemical match using the InChIKey VOKSWYLNZZRQPF-GDIGMMSISA-N
Search UniChem for chemicals with the same backbone VOKSWYLNZZRQPF
Wikipedia Pentazocine