Oxycodone
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 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.
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| Pronunciation | ɒksɪˈkəʊdəʊn |
| 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 |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a682132 |
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| Dependence liability | High |
| Addiction liability | High |
| Routes of administration | By mouth, sublingual, intramuscular, intravenous, intranasal, subcutaneous, transdermal, rectal, epidural |
| Drug class | Opioid |
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| 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 | IR: 10–30 minutes CR: 1 hour |
| Elimination half-life | By mouth (IR): 2–3 hrs (same t1/2 for all ROAs) By mouth (CR): 4.5 hrs |
| Duration of action | By mouth (IR): 3–6 hrs By mouth (CR): 10–12 hrs |
| Excretion | Urine (83%) |
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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. 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 from withdrawal. 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. It was first used medically in Germany in 1917. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2021, it was the 59th 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.