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Oxycodone

For the naturally occurring peptide hormone, see Oxytocin.

Oxycodone
Clinical data
Pronunciation/ɒksiˈkoʊdoʊn/
Trade namesOxyContin, Endone, others
Other namesEukodal, eucodal; dihydrohydroxycodeinone, 7,8-dihydro-14-hydroxycodeinone, 6-deoxy-7,8-dihydro-14-hydroxy-3-O-methyl-6-oxomorphine[1]
AHFS/Drugs.comMonograph
MedlinePlusa682132
License data
Pregnancy
category
Dependence
liability		High[3]
Addiction
liability		High[4]
Routes of
administration		By mouth, sublingual, intramuscular, intravenous, intranasal, subcutaneous, transdermal, rectal, epidural[5]
Drug classOpioid
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityBy mouth: 60–87%[7][8]
Protein binding45%[7]
MetabolismLiver: mainly CYP3A, and, to a much lesser extent, CYP2D6 (~5%);[7] 95% metabolized (i.e., 5% excreted unchanged)[10]
Metabolites• Noroxycodone (25%)[9][10]
• Noroxymorphone (15%, free and conjugated)[9][10]
• Oxymorphone (11%, conjugated)[9][10]
• Others (e.g., minor metabolites)[10]
Onset of actionIRTooltip Instant release: 10–30 minutes[8][10]
CRTooltip controlled release: 1 hour[11]
Elimination half-lifeBy mouth (IR): 2–3 hrs (same t1/2Tooltip biological half-life for all ROAsTooltip routes of administration)[10][8]
By mouth (CR): 4.5 hrs[12]
Duration of actionBy mouth (IR): 3–6 hrs[10]
By mouth (CR): 10–12 hrs[13]
ExcretionUrine (83%)[7]
Identifiers
  • (5R,9R,13S,14S)-4,5α-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.874 Edit this at Wikidata
Chemical and physical data
FormulaC18H21NO4
Molar mass315.369 g·mol−1
3D model (JSmol)
Melting point219 °C (426 °F)
Solubility in water166 (HCl)
  • O=C4[C@@H]5Oc1c2c(ccc1OC)C[C@H]3N(CC[C@]25[C@@]3(O)CC4)C
  • 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 checkY
  • Key:BRUQQQPBMZOVGD-XFKAJCMBSA-N checkY
  (verify)

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]

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]

  1. ^ Cite error: The named reference MerckIndex was invoked but never defined (see the help page).
  2. ^ "Oxycodone Use During Pregnancy". Drugs.com. 14 October 2019. Archived from the original on 19 June 2020. Retrieved 12 April 2020.
  3. ^ Bonewit-West K, Hunt SA, Applegate E (2012). Today's Medical Assistant: Clinical and Administrative Procedures. Elsevier Health Sciences. p. 571. ISBN 978-1-4557-0150-6. Archived from the original on 6 October 2022. Retrieved 20 August 2019.
  4. ^ Bonewit-West K, Hunt SA, Applegate E (2012). Today's Medical Assistant: Clinical and Administrative Procedures. Elsevier Health Sciences. p. 571. ISBN 9781455701506. Archived from the original on 10 January 2023. Retrieved 20 August 2019.
  5. ^ Cite error: The named reference Kalso2005 was invoked but never defined (see the help page).
  6. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  7. ^ a b c d "Roxicodone, OxyContin (oxycodone) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Archived from the original on 13 April 2014. Retrieved 8 April 2014.
  8. ^ a b c Cite error: The named reference ElliottSmith2016 was invoked but never defined (see the help page).
  9. ^ a b c "Roxicodone, OxyContin (oxycodone) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Archived from the original on 13 April 2014. Retrieved 4 January 2019.
  10. ^ a b c d e f g h Cite error: The named reference SmithPassik2008 was invoked but never defined (see the help page).
  11. ^ Yarbro CH, Wujcik D, Gobel BH (15 November 2010). Cancer Nursing: Principles and Practice. Jones & Bartlett Publishers. pp. 695–. ISBN 978-1-4496-1829-2.
  12. ^ Cite error: The named reference McPhersonPincus2016 was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference sunshine1996 was invoked but never defined (see the help page).
  14. ^ Remillard D, Kaye AD, McAnally H (February 2019). "Oxycodone's Unparalleled Addictive Potential: Is it Time for a Moratorium?". Current Pain and Headache Reports. 23 (2): 15. doi:10.1007/s11916-019-0751-7. PMID 30820686. S2CID 73488265.
  15. ^ a b c d e f g h i j "Oxycodone Monograph for Professionals". Drugs.com. AHFS. Archived from the original on 28 December 2018. Retrieved 28 December 2018.
  16. ^ a b Pergolizzi JV, Taylor R, LeQuang JA, Raffa RB (2018). "Managing severe pain and abuse potential: the potential impact of a new abuse-deterrent formulation oxycodone/naltrexone extended-release product". Journal of Pain Research. 11: 301–311. doi:10.2147/JPR.S127602. PMC 5810535. PMID 29445297.
  17. ^ British national formulary : BNF 74 (74 ed.). British Medical Association. 2017. p. 442. ISBN 978-0-85711-298-9.
  18. ^ Talley NJ, Frankum B, Currow D (10 February 2015). Essentials of Internal Medicine 3e. Elsevier Health Sciences. pp. 491–. ISBN 978-0-7295-8081-6.
  19. ^ "Opioid Conversion / Equivalency Table". Stanford School of Medicine, Palliative Care. 20 April 2013. Archived from the original on 9 September 2020. Retrieved 27 October 2017.
  20. ^ Kalso E (May 2005). "Oxycodone". Journal of Pain and Symptom Management. 29 (5 Suppl): S47–S56. doi:10.1016/j.jpainsymman.2005.01.010. PMID 15907646.
  21. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  22. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  23. ^ "Oxycodone – Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
  24. ^ Dart RC, Iwanicki JL, Dasgupta N, Cicero TJ, Schnoll SH (2017). "Do abuse deterrent opioid formulations work?". Journal of Opioid Management. 13 (6): 365–378. doi:10.5055/jom.2017.0415. PMID 29308584.

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