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.
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2D Structure
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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
References
1. Toll L, Berzetei-Gurske IP, Polgar WE, Brandt SR, Adapa ID, Rodriguez L, Schwartz RW, Haggart D, O'Brien A, White A et al.. (1998)
Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications.
NIDA Res. Monogr., 178: 440-66. [PMID:9686407]
2. Zhu J, Luo LY, Li JG, Chen C, Liu-Chen LY. (1997)
Activation of the cloned human kappa opioid receptor by agonists enhances [35S]GTPgammaS binding to membranes: determination of potencies and efficacies of ligands.
J. Pharmacol. Exp. Ther., 282 (2): 676-84. [PMID:9262330]