Opioid medication
For the naturally occurring peptide hormone, see
Oxytocin .
Pharmaceutical compound
Oxycodone Pronunciation Trade names Roxicodone, 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 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 class Opioid ATC code Legal status
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)[ 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 action IR Tooltip Instant release : 10–30 minutes[ 8] [ 10] CR Tooltip controlled release : 1 hour[ 11] Elimination half-life By mouth (IR): 2–3 hrs (same t1/2 Tooltip biological half-life for all ROAs Tooltip routes of administration )[ 10] [ 8] By mouth (CR): 4.5 hrs[ 12] Duration of action By mouth (IR): 3–6 hrs[ 10] By mouth (CR): 10–12 hrs[ 13] Excretion Urine (83%)[ 7]
(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 InfoCard 100.000.874 Formula C 18 H 21 N O 4 Molar mass 315.369 g·mol−1 3D model (JSmol ) Melting point 219 °C (426 °F) Solubility in water 166 (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
Y Key:BRUQQQPBMZOVGD-XFKAJCMBSA-N
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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[ 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.[ 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 in Germany. One year later, it was used medically for the first time 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 2022, it was the 60th 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]
^ Cite error: The named reference MerckIndex
was invoked but never defined (see the help page ).
^ "Oxycodone Use During Pregnancy" . Drugs.com . 14 October 2019. Archived from the original on 19 June 2020. Retrieved 12 April 2020 .
^ 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 .
^ 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 .
^ Cite error: The named reference Kalso2005
was invoked but never defined (see the help page ).
^ "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 .
^ 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 .
^ a b c Cite error: The named reference ElliottSmith2016
was invoked but never defined (see the help page ).
^ 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 .
^ a b c d e f g h Cite error: The named reference SmithPassik2008
was invoked but never defined (see the help page ).
^ 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 .
^ Cite error: The named reference McPhersonPincus2016
was invoked but never defined (see the help page ).
^ Cite error: The named reference sunshine1996
was invoked but never defined (see the help page ).
^ 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 .
^ 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 .
^ 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 .
^ British national formulary : BNF 74 (74 ed.). British Medical Association. 2017. p. 442. ISBN 978-0-85711-298-9 .
^ 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 .
^ "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 .
^ 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 .
^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) . Geneva: World Health Organization. hdl :10665/371090 . WHO/MHP/HPS/EML/2023.02.
^ "The Top 300 of 2022" . ClinCalc . Archived from the original on 30 August 2024. Retrieved 30 August 2024 .
^ "Oxycodone Drug Usage Statistics, United States, 2013 - 2022" . ClinCalc . Retrieved 30 August 2024 .
^ 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 .