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76-42-6 molecular structure
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(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 and InChIs

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

Cite this record

CBID:380 http://www.chembase.cn/molecule-380.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
76-42-6
PubChem SID
46508908
160963843
PubChem CID
5284603

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.562788  H Acceptors
H Donor LogD (pH = 5.5) -1.6110451 
LogD (pH = 7.4) 0.16306217  Log P 1.0348654 
Molar Refractivity 84.0418 cm3 Polarizability 33.020885 Å3
Polar Surface Area 59.0 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.04  LOG S -1.75 
Solubility (Water) 5.59e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
100 mg/ml expand Show data source
Hydrophobicity(logP)
0.3 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00497 external link
Item Information
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

PATENTS

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INTERNET

INTERNET

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