(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-trien-14-ol

• ChemBase编号: 1336
• 分子式: C18H23NO3
• 平均质量: 301.38012
• 单一同位素质量: 301.1677936
• SMILES: O1[C@@H]2[C@]34[C@H]([C@H](N(CC3)C)Cc3c4c1c(OC)cc3)CC[C@@H]2O
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4CC[C@@H]1O)C
• InChI: InChI=1S/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
• InChIKey: RBOXVHNMENFORY-DNJOTXNNSA-N

名称和登记号

名称

• IUPAC标准名: (1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18)-trien-14-ol; (1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-ol
• IUPAC传统名: dihydrocodeine
• 别名: Dihydrocodeine

登记号

• CAS号: 125-28-0
• PubChem SID: 46506478; 160964796
• PubChem CID: 5284543
• ATC码: N02AA08
• CHEMBL: 1595
• Chemspider ID: 4447600
• DrugBank ID: DB01551
• KEGG ID: D07831
• 美国药典/FDA物质标识码: N9I9HDB855
• 维基百科标题: Dihydrocodeine

理论计算性质

JChem

• Acid pKa: 14.151551
• 质子受体: 4
• 质子供体: 1
• LogD (pH = 5.5): -1.7857474
• LogD (pH = 7.4): -0.3756574
• Log P: 1.5489655
• 摩尔折射率: 83.6421 cm^3
• 极化性: 32.852997 Å^3
• 极化表面积: 41.93 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.58
• LOG S: -2.1
• 溶解度: 2.38e+00 g/l

分子性质

药理学性质

• 给药途径: Oral, subcutaneous, I.M., rectal, possiblly sublingual/buccal
• 生物利用度: 20%
• 半衰期: 4 hours
• 代谢: Mainly hepatic, through CYP3A4 and CYP2D6
• 法定药品分级: Class B (UK); S2, S3, S4 depending on dose and other constituents (Australia); Schedule II (US)
• 妊娠期药物分类: C (US)

详细说明

DrugBank - DB01551

• Drug Groups: illicit; experimental
• References: Rowell FJ, Seymour RA, Rawlins MD: Pharmacokinetics of intravenous and oral dihydrocodeine and its acid metabolites. Eur J Clin Pharmacol. 1983;25(3):419-24. [Pubmed] ; Schmidt H, Vormfelde SV, Walchner-Bonjean M, Klinder K, Freudenthaler S, Gleiter CH, Gundert-Remy U, Skopp G, Aderjan R, Fuhr U: The role of active metabolites in dihydrocodeine effects. Int J Clin Pharmacol Ther. 2003 Mar;41(3):95-106. [Pubmed] ; O'Neill WM, Hanks GW, Simpson P, Fallon MT, Jenkins E, Wesnes K: The cognitive and psychomotor effects of morphine in healthy subjects: a randomized controlled trial of repeated (four) oral doses of dextropropoxyphene, morphine, lorazepam and placebo. Pain. 2000 Mar;85(1-2):209-15. [Pubmed]
• External Links: Wikipedia

参考文献

• Rowell FJ, Seymour RA, Rawlins MD: Pharmacokinetics of intravenous and oral dihydrocodeine and its acid metabolites. Eur J Clin Pharmacol. 1983;25(3):419-24. Pubmed
• Schmidt H, Vormfelde SV, Walchner-Bonjean M, Klinder K, Freudenthaler S, Gleiter CH, Gundert-Remy U, Skopp G, Aderjan R, Fuhr U: The role of active metabolites in dihydrocodeine effects. Int J Clin Pharmacol Ther. 2003 Mar;41(3):95-106. Pubmed
• O'Neill WM, Hanks GW, Simpson P, Fallon MT, Jenkins E, Wesnes K: The cognitive and psychomotor effects of morphine in healthy subjects: a randomized controlled trial of repeated (four) oral doses of dextropropoxyphene, morphine, lorazepam and placebo. Pain. 2000 Mar;85(1-2):209-15. Pubmed