buprenorphine   

GtoPdb Ligand ID: 1670

Synonyms: Buprenex® | Buvidal® | CAM2038 | Sixmo® (buprenorphine hydrochloride) | Temgesic®
buprenorphine is an approved drug (FDA (1981), EMA (2006))
Comment: Buprenorphine is a more potent and longer lasting analgesic than morphine.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: buprenorphine

2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 62.16
Molecular weight 467.3
XLogP 3.56
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COC12CCC3(CC1C(C(C)(C)C)(O)C)C14C2Oc2c4c(CC3N(CC1)CC1CC1)ccc2O
Isomeric SMILES CO[C@]12CC[C@]3(C[C@@H]1[C@@](C(C)(C)C)(O)C)[C@@]14[C@H]2Oc2c4c(C[C@H]3N(CC1)CC1CC1)ccc2O
InChI InChI=1S/C29H41NO4/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3/t20-,21-,24-,26+,27-,28+,29-/m1/s1
InChI Key RMRJXGBAOAMLHD-IHFGGWKQSA-N
No information available.
Summary of Clinical Use
Used to treat severe pain and to ameliorate opioid dependence.
Probuphine®, the first buprenorphine implant for the maintenance treatment of opioid dependence was US FDA approved in May 2016. The earliest EMA authorisation was for a fixed dose combination of buprenorphine and naloxone for the treatment of opioid dependence. Approval for buprenorphine use as a monotherapy for this indication was granted in 2018.
Mechanism Of Action and Pharmacodynamic Effects
Buprenorphine appears to act as a partial agonist at μ- and κ-opioid receptors and as an antagonist at δ-opioid receptors.
External links