(1S,5R,13R,17S)-17-hydroxy-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-one

• ChemBase编号: 380
• 分子式: C18H21NO4
• 平均质量: 315.36364
• 单一同位素质量: 315.14705816
• SMILES: O1[C@@H]2[C@]34[C@](O)([C@H](N(CC3)C)Cc3c4c1c(OC)cc3)CCC2=O
• Canonical SMILES: COc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@]4(O)CCC1=O)C
• InChI: InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,13,16,21H,5-9H2,1-2H3/t13-,16+,17+,18-/m1/s1
• InChIKey: BRUQQQPBMZOVGD-XFKAJCMBSA-N

名称和登记号

名称

• IUPAC标准名: (1S,5R,13R,17S)-17-hydroxy-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-one
• IUPAC传统名: oxycodone
• 商标名: Combunox; Dihydroxycodeinone; Dinarkon; Diphydrone; Endocet; Endodan; Endone; Eubine; Eucodal; Eucodalum; Eukodal; Eutagen; Oxanest; Oxicon; Oxicone; Oxikon; Oxycodeinone; Oxycodon; Oxycon; Oxycontin; Pancodine; Percobarb; Percodan; Roxicodone; Supendol; Tecodin; Tekodin; Thecodine; Thekodin; OxyIR; OxyNorm; Percolone; OxyFAST; Supeudol; Remoxy
• 别名: Dihydrohydroxycondeinone; Dihydrohydroxycodeinone; Dihydrone; Oxycodone Hydrochloride; Oxicodona [INN-Spanish]; Oxycodone Hcl; Oxycodonum [INN-Latin]; oxycodone; PTI-821; Oxycodone

登记号

• CAS号: 76-42-6
• PubChem SID: 160963843; 46508908
• PubChem CID: 5284603

理论计算性质

JChem

• Acid pKa: 13.562788
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): -1.6110451
• LogD (pH = 7.4): 0.16306217
• Log P: 1.0348654
• 摩尔折射率: 84.0418 cm^3
• 极化性: 33.020885 Å^3
• 极化表面积: 59.0 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: 1.04
• LOG S: -1.75
• 溶解度: 5.59e+00 g/l

分子性质

理化性质

• 溶解度: 100 mg/ml
• 疏水性(logP): 0.3

详细说明

DrugBank - DB00497

• Drug Groups: illicit; approved; investigational
• Description: Semisynthetic derivative of codeine that acts as a narcotic analgesic more potent and addicting than codeine. [PubChem]
• Indication: For the treatment of diarrhoea, pulmonary oedema and for the relief of moderate to moderately severe pain.
• Pharmacology: Oxycodone, a semisynthetic opiate agonist derived from the opioid alkaloid, thebaine, is similar to other phenanthrene derivatives such as hydrocodone and morphine. Oxycodone is available in combination with aspirin or acetaminophen to control pain and restless leg and Tourette syndromes.
• Toxicity: Symptoms of overdose include respiratory depression, somnolence progressing to stupor or coma, skeletal muscle flaccidity, cold and clammy skin, constricted pupils, bradycardia, hypotension, and death.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Well absorbed with an oral bioavailability of 60% to 87%
• Half Life: 4.5 hours
• Protein Binding: 45%
• Elimination: Oxycodone and its metabolites are excreted primarily via the kidney.
• Distribution: * 2.6 L/kg
• Clearance: * 0.8 L/min [adults]
• References: Ordonez Gallego A, Gonzalez Baron M, Espinosa Arranz E: Oxycodone: a pharmacological and clinical review. Clin Transl Oncol. 2007 May;9(5):298-307. [Pubmed] ; Riley J, Eisenberg E, Muller-Schwefe G, Drewes AM, Arendt-Nielsen L: Oxycodone: a review of its use in the management of pain. Curr Med Res Opin. 2008 Jan;24(1):175-92. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Ordonez Gallego A, Gonzalez Baron M, Espinosa Arranz E: Oxycodone: a pharmacological and clinical review. Clin Transl Oncol. 2007 May;9(5):298-307. Pubmed
• Riley J, Eisenberg E, Muller-Schwefe G, Drewes AM, Arendt-Nielsen L: Oxycodone: a review of its use in the management of pain. Curr Med Res Opin. 2008 Jan;24(1):175-92. Pubmed