Oxycodone

Oxycodone
Clinical data
Pronunciation	/ɒksiˈkoʊdoʊn/
Trade names	Roxicodone, OxyContin, others
Other names	Eukodal, eucodal; dihydrohydroxycodeinone, 7,8-dihydro-14-hydroxycodeinone, 6-deoxy-7,8-dihydro-14-hydroxy-3-O-methyl-6-oxomorphine
AHFS/Drugs.com	Monograph
MedlinePlus	a682132
License data	US DailyMed: Oxycodone;
Pregnancy; category	AU: C;
Dependence; liability	High
Addiction; liability	High
Routes of; administration	By mouth, sublingual, intramuscular, intravenous, intranasal, subcutaneous, transdermal, rectal, epidural
Drug class	Opioid
ATC code	N02AA05 (WHO) ,N02AJ17 (WHO), N02AJ18 (WHO), N02AJ19 (WHO), N02AA55 (WHO), N02AA56 (WHO);
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class A1 (Narcotic drugs); CA: Schedule I; DE: Anlage III (Special prescription form required); UK: Class A; US: Schedule II; UN: Narcotic Schedule I;
Pharmacokinetic data
Bioavailability	By mouth: 60–87%
Protein binding	45%
Metabolism	Liver: mainly CYP3A, and, to a much lesser extent, CYP2D6 (~5%); 95% metabolized (i.e., 5% excreted unchanged)
Metabolites	• Noroxycodone (25%); • Noroxymorphone (15%, free and conjugated); • Oxymorphone (11%, conjugated); • Others (e.g., minor metabolites)
Onset of action	IRTooltip Instant release: 10–30 minutes; CRTooltip controlled release: 1 hour
Elimination half-life	IR: 2–3 hours; CR: 4.5 hours
Duration of action	IR: 3–6 hours; CR: 10–12 hours
Excretion	Urine (83%)
Identifiers
	IUPAC name (5R,9R,13S,14S)-4,5α-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one;
CAS Number	76-42-6 ;
PubChem CID	5284603;
IUPHAR/BPS	7093;
DrugBank	DB00497 ;
ChemSpider	4447649 ;
UNII	CD35PMG570;
KEGG	D05312 ; as HCl: D00847 ;
ChEBI	CHEBI:7852 ;
ChEMBL	ChEMBL656 ;
CompTox Dashboard (EPA)	DTXSID5023407 ;
ECHA InfoCard	100.000.874
Chemical and physical data
Formula	C18H21NO4
Molar mass	315.369 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	219 °C (426 °F)
Solubility in water	166 (HCl)
	SMILES O=C4[C@@H]5Oc1c2c(ccc1OC)C[C@H]3N(CC[C@]25[C@@]3(O)CC4)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 ; Key:BRUQQQPBMZOVGD-XFKAJCMBSA-N ;
	(verify)

Oxycodone, sold under the brand name Roxicodone and OxyContin (which is the extended-release form) among others, is a semi-synthetic opioid used medically for the treatment of moderate to severe pain. It is highly addictive and is a commonly abused drug. It is usually taken by mouth, and is available in immediate-release and controlled-release formulations. Onset of pain relief typically begins within fifteen minutes and lasts for up to six hours with the immediate-release formulation. In the United Kingdom, it is available by injection. Combination products are also available with paracetamol (acetaminophen), ibuprofen, naloxone, naltrexone, and aspirin.

Common side effects include euphoria, constipation, nausea, vomiting, loss of appetite, drowsiness, dizziness, itching, dry mouth, and sweating. Side effects may also include addiction and dependence, substance abuse, irritability, depression or mania, delirium, hallucinations, hypoventilation, gastroparesis, bradycardia, and hypotension. Those allergic to codeine may also be allergic to oxycodone. Use of oxycodone in early pregnancy appears relatively safe. Opioid withdrawal may occur if rapidly stopped. Oxycodone acts by activating the μ-opioid receptor. When taken by mouth, it has roughly 1.5 times the effect of the equivalent amount of morphine.

Oxycodone was originally produced from the opium poppy opiate alkaloid thebaine in 1916 in Germany. One year later, it was used medically for the first time in Germany in 1917. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2022, it was the 60th most commonly prescribed medication in the United States, with more than 11 million prescriptions. A number of abuse-deterrent formulations are available, such as in combination with naloxone or naltrexone.