Oxymorphone

Not to be confused with Oxymorphazone.

Oxymorphone
Clinical data
Trade namesNumorphan, Numorphone, Opana, others
Other names14-Hydroxydihydromorphinone
AHFS/Drugs.comMonograph
MedlinePlusa610022
License data
Dependence
liability		High
Addiction
liability		High
Routes of
administration		By mouth, buccal, sublingual, intranasal, intravenous, epidural, subcutaneous, intramuscular
Drug classOpioid
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityby mouth: 10%
Buccal: 28%
Sublingual: 37.5%
Intranasal: 43%[3]
IV, IM & IT: 100%[4]
Protein binding10%[4]
MetabolismLiver (CYP3A4, glucuronidation)[4]
Metabolites• Noroxymorphone
• glucuronide
Elimination half-life10–12 hours[5]
Duration of actionDuration of action: 6–8 hours orally, 4–6 hrs parenteral
ExcretionUrine, feces[4]
Identifiers
  • 4,5α-Epoxy-3,14-dihydroxy-17-methylmorphinan-6-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.873 Edit this at Wikidata
Chemical and physical data
FormulaC17H19NO4
Molar mass301.342 g·mol−1
3D model (JSmol)
  • CN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C5
  • InChI=1S/C17H19NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-3,12,15,19,21H,4-8H2,1H3/t12-,15+,16+,17-/m1/s1 checkY
  • Key:UQCNKQCJZOAFTQ-ISWURRPUSA-N checkY
  (verify)

Oxymorphone (sold under the brand names Numorphan and Opana among others) is a highly potent opioid analgesic indicated for treatment of severe pain. Pain relief after injection begins after about 5–10 minutes, after oral administration it begins after about 30 minutes, and lasts about 3–4 hours for immediate-release tablets and 12 hours for extended-release tablets.[6] The elimination half-life of oxymorphone is much faster intravenously, and as such, the drug is most commonly used orally.[7] Like oxycodone, which metabolizes to oxymorphone, oxymorphone has a high potential to be abused.[8]

It was developed in Germany in 1914. It was patented in 1955 and approved for medical use in 1959.[9] In June 2017 the FDA asked Endo Pharmaceuticals to remove its product from the US market.[10] This was in part due to the opioid epidemic in the US, and the fact that a 2012 reformulation failed to stop illicit injection of the drug. Endo responded by voluntarily removing Opana ER from the market a month later.[11] Generic versions of extended-release oxymorphone, such as those manufactured by Amneal Pharmaceuticals, are still available in the US.[12]

  1. ^ "Drugs@FDA: FDA Approved Drug Products". www.accessdata.fda.gov. Retrieved 7 November 2017.
  2. ^ Anvisa (31 March 2023). "RDC Nº 784 – Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 – Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  3. ^ Hussain MA, Aungst BJ (August 1997). "Intranasal absorption of oxymorphone". Journal of Pharmaceutical Sciences. 86 (8): 975–6. doi:10.1021/js960513x. PMID 9269879.
  4. ^ a b c d Davis MP, Glare PA, Hardy J (2009) [2005]. Opioids in Cancer Pain (2nd ed.). Oxford, UK: Oxford University Press. pp. Chapter 17. ISBN 978-0-19-157532-7.
  5. ^ Polsten GR, Wallace MS (21 June 2016). "Analgesic Agents in Rheumatic Disease". In Firestein GS, Budd R, Gabriel SE, McInnes IB, O'Dell JR (eds.). Kelley and Firestein's Textbook of Rheumatology. Elsevier Health Sciences. pp. 1081–. ISBN 978-0-323-41494-4.
  6. ^ Sloan P (August 2008). "Review of oral oxymorphone in the management of pain". Therapeutics and Clinical Risk Management. 4 (4): 777–87. doi:10.2147/tcrm.s1784. PMC 2621383. PMID 19209260.
  7. ^ Smith HS (1 April 2009). "Clinical Pharmacology of Oxymorphone". Pain Medicine. 10 (suppl_1): S3–S10. doi:10.1111/j.1526-4637.2009.00594.x. ISSN 1526-2375.
  8. ^ Babalonis S, Lofwall MR, Nuzzo PA, Walsh SL (January 2016). "Pharmacodynamic effects of oral oxymorphone: abuse liability, analgesic profile and direct physiologic effects in humans". Addiction Biology. 21 (1): 146–58. doi:10.1111/adb.12173. PMC 4383736. PMID 25130052.
  9. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 52X. ISBN 9783527607495.
  10. ^ Wolf LK (19 June 2017). "FDA takes aim at opioid epidemic". Chemical & Engineering News. 95 (25): 8.
  11. ^ Office of the Commissioner (10 September 2019). "Press Announcements – FDA requests removal of Opana ER for risks related to abuse". www.fda.gov.
  12. ^ Bernstein L, Merle R (27 November 2019). "Six drug companies subpoenaed in federal opioids probe". The Washington Post. Retrieved 18 April 2020.