User:Mr. Ibrahem/Oxycodone

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Mr. Ibrahem/Oxycodone
Clinical data
Pronunciationɒksɪˈkəʊdəʊn
Trade namesOxyContin, 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]
Routes of
administration		By mouth, sublingual, intramuscular, intravenous, intranasal, subcutaneous, transdermal, rectal, epidural[4]
Drug classOpioid[5]
Legal status
Legal status
Pharmacokinetic data
BioavailabilityBy mouth: 60–87%[6][7]
Protein binding45%[6]
MetabolismLiver: mainly CYP3A, and, to a much lesser extent, CYP2D6 (~5%);[6] 95% metabolized (i.e., 5% excreted unchanged)[9]
Metabolites• Noroxycodone (25%) [8][9]
• Noroxymorphone (15%, free and conjugated)[8][9]
• Oxymorphone (11%, conjugated)[8][9]
• Others (e.g., minor metabolites)[9]
Onset of actionIRTooltip Instant release: 10–30 minutes[7][9]
CRTooltip controlled release: 1 hour[10]
Elimination half-lifeBy mouth (IR): 2–3 hrs (same t1/2Tooltip biological half-life for all ROAsTooltip routes of administration)[9][7]
By mouth (CR): 4.5 hrs[11]
Duration of actionBy mouth (IR): 3–6 hrs[9]
By mouth (CR): 10–12 hrs[12]
ExcretionUrine (83%)[6]
Identifiers
  • (5R,9R,13S,14S)-4,5α-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
Chemical and physical data
FormulaC18H21NO4
Molar mass315.369 g·mol−1
3D model (JSmol)
Melting point219 °C (426 °F)
Solubility in waterHCl: 166
  • 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 the brand name OxyContin among others, is an opioid medication used for treatment of moderate to severe pain.[5] It is usually taken by mouth, and is available in immediate-release and controlled-release formulations.[5] Onset of pain relief typically begins within 15 minutes and lasts for up to six hours with the immediate-release formulation.[5] In the United Kingdom, it is available by injection.[15] Combination products are also available with paracetamol (acetaminophen), ibuprofen, naloxone, and aspirin.[5]

Common side effects include constipation, nausea, sleepiness, dizziness, itching, dry mouth, and sweating.[5] Severe side effects may include addiction, respiratory depression (a reduction in breathing), and low blood pressure.[5] Those allergic to codeine may also be allergic to oxycodone.[5] Use of oxycodone in early pregnancy appears relatively safe.[5] Opioid withdrawal may occur if rapidly stopped.[5] Oxycodone acts by activating the μ-opioid receptor.[16] When taken by mouth, it has roughly 1.5 times the effect of the equivalent amount of morphine.[17]

Oxycodone was first made in Germany in 1916 from thebaine.[18] It is on the World Health Organization's List of Essential Medicines as an alternative to morphine.[19] It is available as a generic medication.[5] In the United States, the wholesale cost per dose is less than US$0.30 as of 2018.[20] In 2017, it was the 52nd most commonly prescribed medication in the United States, with more than 15 million prescriptions.[21][22] Oxycodone has been a common drug of abuse.[23] A number of abuse-deterrent formulations are available, such as in combination with naloxone.[23][24]

References[edit]

  1. ^ O'Neil, Maryadele J., ed. (2006). The Merck index (14 ed.). Whitehouse Station, NJ: Merck & Co. ISBN 978-0-911910-00-1.
  2. ^ a b "Oxycodone Use During Pregnancy". Drugs.com. 14 October 2019. Archived from the original on 19 June 2020. Retrieved 12 April 2020.
  3. ^ Bonewit-West, Kathy; Hunt, Sue A.; Applegate, Edith (2012). Today's Medical Assistant: Clinical and Administrative Procedures. Elsevier Health Sciences. p. 571. ISBN 9781455701506. Archived from the original on 2020-07-28. Retrieved 2020-08-05.
  4. ^ Kalso E (2005). "Oxycodone". Journal of Pain and Symptom Management. 29 (5S): S47–S56. doi:10.1016/j.jpainsymman.2005.01.010. PMID 15907646.
  5. ^ a b c d e f g h i j k l m "Oxycodone Monograph for Professionals". Drugs.com. AHFS. Archived from the original on 28 December 2018. Retrieved 28 December 2018.
  6. ^ 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.
  7. ^ a b c Jennifer A. Elliott; Howard S. Smith (19 April 2016). Handbook of Acute Pain Management. CRC Press. pp. 82–. ISBN 978-1-4665-9635-1. Archived from the original on 17 April 2021. Retrieved 5 August 2020.
  8. ^ 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.
  9. ^ a b c d e f g h Howard Smith; Steven Passik (25 April 2008). Pain and Chemical Dependency. Oxford University Press USA. pp. 195–. ISBN 978-0-19-530055-0. Archived from the original on 17 April 2021. Retrieved 5 August 2020.
  10. ^ Connie Henke Yarbro; Debra Wujcik; Barbara Holmes Gobel (15 November 2010). Cancer Nursing: Principles and Practice. Jones & Bartlett Publishers. pp. 695–. ISBN 978-1-4496-1829-2. Archived from the original on 27 February 2020. Retrieved 5 August 2020.
  11. ^ Richard A. McPherson; Matthew R. Pincus (31 March 2016). Henry's Clinical Diagnosis and Management by Laboratory Methods. Elsevier Health Sciences. pp. 336–. ISBN 978-0-323-41315-2.
  12. ^ Sunshine, Abraham; Olson, Nancy Z.; Colon, Ariel; Rivera, Juana; Kaiko, Robert F.; Fitzmartin, Ronald D.; Reder, Robert F.; Goldenheim, Paul D. (July 1996). "Analgesic Efficacy of Controlled-Release Oxycodone in Postoperative Pain". Journal of Clinical Pharmacology. 36 (7): 595–603. doi:10.1002/j.1552-4604.1996.tb04223.x. PMID 8844441. Treatment with CR oxycodone was safe and effective in this study, and its characteristics will be beneficial in the treatment of pain.
  13. ^ a b "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 6 August 2020. Retrieved 9 September 2020.
  14. ^ "Interpreting Urine Drug Tests (UDT)". Archived from the original on 25 October 2023. Retrieved 24 October 2023.
  15. ^ British national formulary : BNF 74 (74 ed.). British Medical Association. 2017. p. 442. ISBN 978-0857112989.
  16. ^ Nicholas J Talley; Brad Frankum; David Currow (10 February 2015). Essentials of Internal Medicine 3e. Elsevier Health Sciences. pp. 491–. ISBN 978-0-7295-8081-6. Archived from the original on 3 August 2020. Retrieved 5 August 2020.
  17. ^ "Stanford School of Medicine, Palliative Care, Opioid Conversion / Equivalency Table". 2013-04-20. Archived from the original on 2020-09-09. Retrieved 2020-08-05. {{cite journal}}: Cite journal requires |journal= (help)
  18. ^ Sneader, W. (2005). Drug discovery: a history. Hoboken, NJ: Wiley. p. 119. ISBN 978-0-471-89980-8.
  19. ^ 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.
  20. ^ "NADAC as of 2018-12-19". Centers for Medicare and Medicaid Services. Archived from the original on 2018-12-19. Retrieved 22 December 2018.
  21. ^ "The Top 300 of 2020". ClinCalc. Archived from the original on 12 February 2021. Retrieved 11 April 2020.
  22. ^ "Oxycodone - Drug Usage Statistics". ClinCalc. Archived from the original on 11 April 2020. Retrieved 11 April 2020.
  23. ^ a b Pergolizzi JV, Jr; Taylor R, Jr; 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)
  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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