(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 ID: 380
• Molecular Formular: C18H21NO4
• Molecular Mass: 315.36364
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: oxycodone
• Brand Name: 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
• Synonyms: Dihydrohydroxycondeinone; Dihydrohydroxycodeinone; Dihydrone; Oxycodone Hydrochloride; Oxicodona [INN-Spanish]; Oxycodone Hcl; Oxycodonum [INN-Latin]; oxycodone; PTI-821; Oxycodone

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.562788
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.6110451
• LogD (pH = 7.4): 0.16306217
• Log P: 1.0348654
• Molar Refractivity: 84.0418 cm^3
• Polarizability: 33.020885 Å^3
• Polar Surface Area: 59.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.04
• LOG S: -1.75
• Solubility (Water): 5.59e+00 g/l

PROPERTIES

Physical Property

• Solubility: 100 mg/ml
• Hydrophobicity(logP): 0.3

DETAILS

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

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