(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7(12),8,10-trien-11-ol

• ChemBase ID: 126279
• Molecular Formular: C29H41NO4
• Molecular Mass: 467.64014
• Monoisotopic Mass: 467.3035588
• SMILES: Oc1ccc2c3c1O[C@H]1[C@]4(OC)[C@H](C[C@@]5([C@H](N(CC[C@]315)CC1CC1)C2)CC4)C(O)(C)C(C)(C)C
• Canonical SMILES: CO[C@]12CC[C@]3(C[C@@H]1C(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
• InChIKey: RMRJXGBAOAMLHD-IHFGGWKQSA-N

NAMES AND DATABASE IDS

Names

• 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,^1^4.0^7,^1^2]icosa-7(12),8,10-trien-11-ol
• IUPAC Traditional name: buprenorphine
• Brand Name: Buprenex, Subutex, Suboxone, Butrans
• Synonyms: Buprenorphine

Database IDs

• CAS Number: 52485-79-7
• PubChem SID: 162220618
• PubChem CID: 644073
• CHEBI ID: 3216
• ATC CODE: N02AE01; N07BC01
• CHEMBL: 1201894
• Chemspider ID: 559124
• DrugBank ID: DB00921
• IUPHAR ligand ID: 1670
• KEGG ID: D07132
• Unique Ingredient Identifier: 40D3SCR4GZ
• Wikipedia Title: Buprenorphine
• Medline Plus: a605002

CALCULATED PROPERTIES

• Acid pKa: 7.503442
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.9028575
• LogD (pH = 7.4): 2.321925
• Log P: 2.6713505
• Molar Refractivity: 131.7623 cm^3
• Polarizability: 52.271748 Å^3
• Polar Surface Area: 62.16 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Admin Routes: sublingual, IM, IV, transdermal, intranasal, rectallyon
• Bioavailability: 55%(sublingual)/48.2% +/- 8.35%(intranasal)
• Excretion: biliary and renal
• Half Life: 20–70, mean 37 hours
• Metabolism: hepatic; CYP3A4, CYP2C8
• Protein Bound: 96%
• Legal Status: Schedule III (V some states) (USA); Schedule 8 (Aust); Class C(UK); Cat. A Singapore; Schedule III Germany
• Pregnancy Category: C (USA)