(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编号: 126279
• 分子式: C29H41NO4
• 平均质量: 467.64014
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: buprenorphine
• 商标名: Buprenex, Subutex, Suboxone, Butrans
• 别名: Buprenorphine

登记号

• CAS号: 52485-79-7
• PubChem SID: 162220618
• PubChem CID: 644073
• CHEBI ID: 3216
• ATC码: N07BC01; N02AE01
• CHEMBL: 1201894
• Chemspider ID: 559124
• DrugBank ID: DB00921
• IUPHAR配体索引: 1670
• KEGG ID: D07132
• 美国药典/FDA物质标识码: 40D3SCR4GZ
• 维基百科标题: Buprenorphine
• Medline Plus: a605002

理论计算性质

• Acid pKa: 7.503442
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 0.9028575
• LogD (pH = 7.4): 2.321925
• Log P: 2.6713505
• 摩尔折射率: 131.7623 cm^3
• 极化性: 52.271748 Å^3
• 极化表面积: 62.16 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

药理学性质

• 给药途径: sublingual, IM, IV, transdermal, intranasal, rectallyon
• 生物利用度: 55%(sublingual)/48.2% +/- 8.35%(intranasal)
• 排泄: biliary and renal
• 半衰期: 20–70, mean 37 hours
• 代谢: hepatic; CYP3A4, CYP2C8
• 蛋白结合率: 96%
• 法定药品分级: Schedule III (V some states) (USA); Schedule 8 (Aust); Class C(UK); Cat. A Singapore; Schedule III Germany
• 妊娠期药物分类: C (USA)