Oxycodone

Title: Oxycodone
CAS Registry Number: 76-42-6
CAS Name: (5a)-4,5-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
Additional Names: 6-deoxy-7,8-dihydro-14-hydroxy-3-O-methyl-6-oxomorphine; dihydrohydroxycodeinone; 14-hydroxydihydrocodeinone
Trademarks: Dihydrone
Molecular Formula: C18H21NO4
Molecular Weight: 315.36
Percent Composition: C 68.55%, H 6.71%, N 4.44%, O 20.29%
Literature References: m-Opioid receptor agonist. Prepn from thebaine: M. Freund, E. Speyer, J. Prakt. Chem. 94, 135 (1916); R. Krassnig et al., Arch. Pharm. 329, 325 (1996); from codeine: A. J. Walker, N. C. Bruce, Tetrahedron 60, 561 (2004). Bibliography: Small, Lutz, "Chemistry of the Opium Alkaloids," Suppl. No. 103 to Public Health Reports, Washington (1932); K. W. Bentley, The Chemistry of the Morphine Alkaloids (Oxford, 1954). In vitro liposolubility and protein binding: R. Pöyhiä, T. Seppälä, Pharmacol. Toxicol. 74, 23 (1994). HPLC determn in serum: A. W. E. Wright et al., J. Chromatogr. B 712, 169 (1998). Review of pharmacokinetics and clinical experience: E. Kalso, J. Pain Symptom Manage. 29, S47-S56 (2005); of abuse potential: T. J. Cicero et al., J. Pain 6, 662-672 (2005).
Properties: Long rods from alc, mp 218-220°. pKa 8.53. Sol in alcohol, chloroform. Nearly insol in ether, water, KOH, NaOH, NH4OH.
Melting point: mp 218-220°
pKa: pKa 8.53
Derivative Type: Hydrochloride
CAS Registry Number: 124-90-3
Trademarks: Dinarkon (Biotika); Eubine (Chiesi); Eukodal (Merck KGaA); OxyContin (Purdue); Oxygesic (Mundipharma); Oxynorm (Mundipharma); Supeudol (Sabex)
Molecular Formula: C18H21NO4.HCl
Molecular Weight: 351.82
Percent Composition: C 61.45%, H 6.30%, N 3.98%, O 18.19%, Cl 10.08%
Properties: Component of Percocet (Endo) and Percodan (Endo) . Long rods from water, dec 270-272°. [a]D20 -125° (c = 2.5). Partition coefficient (octanol/water): 0.7. One gram dissolves in 6-7 ml water. Slightly sol in alcohol.
Optical Rotation: [a]D20 -125° (c = 2.5)
Log P: Partition coefficient (octanol/water): 0.7
Derivative Type: Pectinate
CAS Registry Number: 9012-92-4
Trademarks: Proladone (Abbott)
Properties: Used for prolonged action.
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.12.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).
Oxyfedrine Oxyfluorfen Oxymetazoline Oxymethurea Oxypendyl

Oxycodone
Oxycodone.svg
Oxycodone3.png
Systematic (IUPAC) name
(5R,9R,13S,14S)-4,5α-epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
Clinical data
Trade names Roxicodone, OxyContin, Oxecta, OxyIR, Endone
AHFS/Drugs.com monograph
MedlinePlus a682132
Pregnancy cat. B/D (prolonged use or in high doses at term)
Legal status Controlled (S8) (AU) Schedule I (CA) Class A (CD)Schedule II (UK) Schedule II (US)
Dependence liability Moderate–High
Routes oral, intramuscular, intravenous, intranasal, subcutaneous, transdermal, rectal, epidural[1]
Pharmacokinetic data
Bioavailability Up to 87% (oral)[2]
Protein binding 45%
Metabolism Hepatic: primarily CYP3A, secondarily CYP2D6[3]
Half-life 3–4.5 h
Excretion Urine (19% unchanged)
Identifiers
CAS number 76-42-6 YesY
ATC code N02AA05
N02AA55 (in combinations)
PubChem CID 5284603
DrugBank DB00497
ChemSpider 4447649 YesY
UNII CD35PMG570 YesY
KEGG D05312 YesY
ChEBI CHEBI:7852 YesY
ChEMBL CHEMBL656 YesY
Synonyms dihydrohydroxycodeinone, 14-hydroxydihydrocodeinone, 6-deoxy-7,8-dihydro-14-hydroxy-3-O-methyl-6-oxomorphine[4]
Chemical data
Formula C18H21NO4 
Mol. mass 315.364 g/mol
Physical data
Solubility in water HCl: 166 mg/mL (20 °C)
 YesY (what is this?)  (verify)

Oxycodone is a semi-synthetic opioid synthesized from poppy-derived thebaine. It is a narcotic analgesic generally indicated for relief of moderate to severe pain. It was developed in 1916 in Germany[5][6] as one of several new semi-synthetic opioids in an attempt to improve on the existing opioids.[1]

Oxycodone is available as single-ingredient medication in immediate release and controlled release. Combination products formulated with non-narcotic ingredients such as NSAIDs and paracetamol (acetaminophen) are also available as immediate release formulations.