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
Classification
Compound class Natural product or derivative
Approved drug? Yes (FDA (1981), EMA (2006))
IUPAC Name
(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1^{2,8}.0^{1,6}.0^{6,14}.0^{7,12}]icosa-7(12),8,10-trien-11-ol
International Nonproprietary Names
INN number INN
3403 buprenorphine
Synonyms
Buprenex® | Buvidal® | CAM2038 | Sixmo® (buprenorphine hydrochloride) | Temgesic®
Database Links
CAS Registry No. 52485-79-7 (source: Scifinder)
ChEBI CHEBI:3216
ChEMBL Ligand CHEMBL560511
DrugBank Ligand DB00921
DrugCentral Ligand 434
GtoPdb PubChem SID 135652673
PubChem CID 644073
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Wikipedia Buprenorphine