OxyContin

Oxycodone

Clinical data
Trade names	many
AHFS/Drugs.com	Monograph
MedlinePlus	a682132
Pregnancy category	AU: C US: B (No risk in non-human studies)
Dependence liability	High
Routes of administration	By mouth, sublingual, intramuscular, intravenous, intranasal, subcutaneous, transdermal, rectal, epidural
ATC code	N02AA05 (WHO) N02AA55 (WHO) (in combinations)
Legal status
Legal status	AU: S8 (Controlled) CA: Schedule I DE: Anlage III (Prescription only) UK: Class A US: Schedule II
Pharmacokinetic data
Bioavailability	60–87%
Protein binding	45%
Metabolism	Hepatic: mainly CYP3A, and, to a much lesser extent, CYP2D6 to oxymorphone (~5%); 95% metabolized (i.e., 5% excreted unchanged)
Onset of action	10–30 minutes (IR) 1 hour (CR)
Biological half-life	2–3 hours (IR) (variable) (same t1/2 for all ROAs) 4.5 hours (CR)
Duration of action	3–6 hours (IR) (variable) 12 hours (CR)
Excretion	Urine (83%)
Identifiers
IUPAC name (5R,9R,13S,14S)-4,5α-epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
Synonyms	Eukodal, eucodal; dihydrohydroxycodeinone, 7,8-dihydro-14-hydroxycodeinone, 6-deoxy-7,8-dihydro-14-hydroxy-3-O-methyl-6-oxomorphine
CAS Number	76-42-6 Y
PubChem CID	5284603
IUPHAR/BPS	7093
DrugBank	DB00497 Y
ChemSpider	4447649 Y
UNII	CD35PMG570
KEGG	D05312 Y
ChEBI	CHEBI:7852 Y
ChEMBL	CHEMBL656 Y
ECHA InfoCard	100.000.874
Chemical and physical data
Formula	C18H21NO4
Molar mass	315.364 g/mol
3D model (Jmol)	Interactive image
Solubility in water	HCl: 166 mg/mL (20 °C)
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 Y Key:BRUQQQPBMZOVGD-XFKAJCMBSA-N Y

Oxycodone is a semisynthetic opioid synthesized from thebaine, an opioid alkaloid found in the Persian poppy, and one of the many alkaloids found in the opium poppy. It is a moderately potent opioid analgesic, generally indicated for relief of moderate to severe pain. Oxycodone was developed in 1917 in Germany as one of several semi-synthetic opioids in an attempt to improve on the existing opioids.

Oxycodone is available as single-ingredient medication in immediate release and controlled release. Parenteral formulations of 10 mg/mL and 50 mg/mL are available in the UK for IV/IM administration. Combination products are also available as immediate-release formulations, with non-narcotic analgesic ingredients such as paracetamol (acetaminophen) and nonsteroidal anti-inflammatory drugs (NSAIDs), including aspirin and ibuprofen. An abuse-deterrent combination with naloxone is available in managed-release tablets. If injected, the naloxone precipitates opioid withdrawal symptoms and blocks the effect of the medication.

Oxycodone has been in clinical use since 1916, and it is used for managing moderate to moderately severe acute or chronic pain. It has been found to improve quality of life for those with many types of pain. Experts are divided regarding use for non-cancer-related chronic pain, as most opioids have great potential for dependence and may also create paradoxical pain sensitivity.

Oxycodone is available as controlled-release tablet, intended to be taken every 12 hours. A 2006 review found that controlled-release oxycodone is comparable to instant-release oxycodone, morphine, and hydromorphone in management of moderate to severe cancer pain, with fewer side effects than morphine. The author concluded that the controlled release form is a valid alternative to morphine and a first-line treatment for cancer pain. In 2014, the European Association for Palliative Care recommended oral oxycodone as a second-line alternative to oral morphine for cancer pain.