buprenorphine

Term ID

CHEBI:3216

Synonyms

• (-)-buprenorphine
• (5alpha,6beta,14beta,18R)-17-(cyclopropylmethyl)-18-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol
• 17-cyclopropylmethyl-4,5alpha-epoxy-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-ol
• 2-(N-cyclopropylmethyl-4,5alpha-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6alpha-yl)-3,3-dimethyl-2-butanol
• 2-[3-cyclopropylmethyl-11-hydroxy-15-methoxy-(14R)-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-16-yl]-3,3-dimethyl-2-butanol
• 21-cyclopropyl-7alpha-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine
• buprenorfina
• Buprenorphine
• buprenorphinum

Definition

A morphinane alkaloid that is 7,8-dihydromorphine 6-O-methyl ether in which positions 6 and 14 are joined by a -CH₂CH₂- bridge, one of the hydrogens of the N-methyl group is substituted by cyclopropyl, and a hydrogen at position 7 is substituted by a 2-hydroxy-3,3-dimethylbutan-2-yl group. It is highly effective for the treatment of opioid use disorder and is also increasingly being used in the treatment of chronic pain.

References

• beilstein:6182863
• cas:52485-79-7
• chemspider:559124
• drugbank:DB00921
• drugcentral:434
• hmdb:HMDB0015057
• kegg.compound:C08007
• kegg.drug:D07132
• metacyc.compound:CPD-22086
• patent:GB1136214
• patent:US3433791
• pmc:PMC7711199
• pubmed:10649968
• pubmed:11303059
• pubmed:15181649
• pubmed:15781180
• pubmed:16642964
• pubmed:16650985
• pubmed:17887741
• pubmed:18997874
• pubmed:19402772
• pubmed:32925232
• pubmed:33378137
• vsdb:1789
• wikipedia.en:Buprenorphine

Ontology

ChEBI  ( EBI )

Resources

CTD