buprenorphine   Click here for help

GtoPdb Ligand ID: 1670

Synonyms: Buprenex® | Buvidal® | CAM2038 | Sixmo® (buprenorphine hydrochloride) | Subutex® | Temgesic®
Approved drug
buprenorphine is an approved drug (FDA (1981), EMA (2006))
Compound class: Synthetic organic
Comment: Buprenorphine is a more potent and longer lasting analgesic than morphine. It is a semisynthetic derivative of thebaine (paramorphine).
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: buprenorphine

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1981), EMA (2006))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
3403 buprenorphine
Synonyms Click here for help
Buprenex® | Buvidal® | CAM2038 | Sixmo® (buprenorphine hydrochloride) | Subutex® | Temgesic®
Database Links Click here for help
Specialist databases
GPCRdb Ligand buprenorphine
Other databases
CAS Registry No. 52485-79-7 (source: Scifinder)
ChEMBL Ligand CHEMBL560511
DrugBank Ligand DB00921
DrugCentral Ligand 434
GtoPdb PubChem SID 135652673
PubChem CID 644073
Search Google for chemical match using the InChIKey RMRJXGBAOAMLHD-IHFGGWKQSA-N
Search Google for chemicals with the same backbone RMRJXGBAOAMLHD
Search PubMed clinical trials buprenorphine
Search PubMed titles buprenorphine
Search PubMed titles/abstracts buprenorphine
UniChem Compound Search for chemical match using the InChIKey RMRJXGBAOAMLHD-IHFGGWKQSA-N
UniChem Connectivity Search for chemical match using the InChIKey RMRJXGBAOAMLHD-IHFGGWKQSA-N
Wikipedia Buprenorphine