Oxycodone
Opioid medication / From Wikipedia, the free encyclopedia
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Oxycodone, sold under various brand names such as Roxicodone and OxyContin (which is the extended release form), is a semi-synthetic opioid used medically for treatment of moderate to severe pain. It is highly addictive[14] and is a commonly abused drug.[15][16] It is usually taken by mouth, and is available in immediate-release and controlled-release formulations.[15] Onset of pain relief typically begins within fifteen minutes and lasts for up to six hours with the immediate-release formulation.[15] In the United Kingdom, it is available by injection.[17] Combination products are also available with paracetamol (acetaminophen), ibuprofen, naloxone, naltrexone, and aspirin.[15]
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Pronunciation | /ɒksiˈkoʊdoʊn/ |
Trade names | OxyContin, Endone, others |
Other names | Eukodal, eucodal; dihydrohydroxycodeinone, 7,8-dihydro-14-hydroxycodeinone, 6-deoxy-7,8-dihydro-14-hydroxy-3-O-methyl-6-oxomorphine[1] |
AHFS/Drugs.com | Monograph |
MedlinePlus | a682132 |
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Dependence liability | High[3] |
Addiction liability | High[4] |
Routes of administration | By mouth, sublingual, intramuscular, intravenous, intranasal, subcutaneous, transdermal, rectal, epidural[5] |
Drug class | Opioid |
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Bioavailability | By mouth: 60–87%[7][8] |
Protein binding | 45%[7] |
Metabolism | Liver: mainly CYP3A, and, to a much lesser extent, CYP2D6 (~5%);[7] 95% metabolized (i.e., 5% excreted unchanged)[9] |
Metabolites | • Noroxycodone (25%)[10][9] • Noroxymorphone (15%, free and conjugated)[10][9] • Oxymorphone (11%, conjugated)[10][9] • Others (e.g., minor metabolites)[9] |
Onset of action | IRTooltip Instant release: 10–30 minutes[8][9] CRTooltip controlled release: 1 hour[11] |
Elimination half-life | By mouth (IR): 2–3 hrs (same t1/2Tooltip biological half-life for all ROAsTooltip routes of administration)[9][8] By mouth (CR): 4.5 hrs[12] |
Duration of action | By mouth (IR): 3–6 hrs[9] By mouth (CR): 10–12 hrs[13] |
Excretion | Urine (83%)[7] |
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ECHA InfoCard | 100.000.874 |
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Formula | C18H21NO4 |
Molar mass | 315.369 g·mol−1 |
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Melting point | 219 °C (426 °F) |
Solubility in water | 166 (HCl) |
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Common side effects include euphoria, constipation, nausea, vomiting, loss of appetite, drowsiness, dizziness, itching, dry mouth, and sweating.[15] Side effects may also include addiction and dependence, substance abuse, irritability, depression or mania, delirium, hallucinations, hypoventilation, gastroparesis, bradycardia, and hypotension.[15] Those allergic to codeine may also be allergic to oxycodone.[15] Use of oxycodone in early pregnancy appears relatively safe.[15] Opioid withdrawal may occur if rapidly stopped from withdrawal.[15] Oxycodone acts by activating the μ-opioid receptor.[18] When taken by mouth, it has roughly 1.5 times the effect of the equivalent amount of morphine.[19]
Oxycodone was originally produced from the opium poppy opiate alkaloid thebaine in 1916. It was first used medically in Germany in 1917.[20] It is on the World Health Organization's List of Essential Medicines.[21] It is available as a generic medication.[15] In 2021, it was the 59th most commonly prescribed medication in the United States, with more than 11 million prescriptions.[22][23] A number of abuse-deterrent formulations are available, such as in combination with naloxone or naltrexone.[16][24]