Buprenorphine
(1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol
Molecular Identity
Buprenorphine
(1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol
PubChem CID: 644073
Buprenorphine is 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. It has a role as a kappa-opioid receptor antagonist, an opioid analgesic, a mu-opioid receptor agonist and a delta-opioid receptor antagonist.
2D Structure
Properties
C29H41NO4
Molecular Formula
467.60
Molecular Weight
g/mol
467.3036
Exact Mass
Da
5
XLogP
Above Lipinski threshold
62.2
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
5
H-Bond Acceptors
869
Complexity
SMILES
Canonical SMILES
SMILES: CC(C)(C)C(C)(C1CC23CCC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)OIsomeric SMILES
SMILES: C[C@]([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)(C(C)(C)C)OSynonyms(20)
buprenorphineTemgesic52485-79-7BuprenophineBuprenorfinaBuprenorphinumButrans(-)-buprenorphinebuprenorphinSublocadeBrixadiCHEBI:321640D3SCR4GZCAM2038DTXSID2022705
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Buprenorphine
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