Oxymorphone

Oxymorphone
Clinical data
Trade names	Numorphan, Numorphone, Opana, others
Other names	14-Hydroxydihydromorphinone
AHFS/Drugs.com	Monograph
MedlinePlus	a610022
License data	US DailyMed: Oxymorphone;
Dependence; liability	High
Addiction; liability	High
Routes of; administration	By mouth, buccal, sublingual, intranasal, intravenous, epidural, subcutaneous, intramuscular
Drug class	Opioid
ATC code	N02AA11 (WHO) ;
Legal status
Legal status	AU: S8 (Controlled drug); BR: Class A1 (Narcotic drugs); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class A; US: Schedule II;
Pharmacokinetic data
Bioavailability	by mouth: 10%; Buccal: 28%; Sublingual: 37.5%; Intranasal: 43%; IV, IM & IT: 100%
Protein binding	10%
Metabolism	Liver (CYP3A4, glucuronidation)
Metabolites	• Noroxymorphone; • glucuronide
Elimination half-life	10–12 hours
Duration of action	Duration of action: 6–8 hours orally, 4–6 hrs parenteral
Excretion	Urine, feces
Identifiers
	IUPAC name 4,5α-Epoxy-3,14-dihydroxy-17-methylmorphinan-6-one;
CAS Number	76-41-5 ;
PubChem CID	5284604;
IUPHAR/BPS	7094;
DrugBank	DB01192 ;
ChemSpider	4447650 ;
UNII	9VXA968E0C;
KEGG	D08323 ;
ChEMBL	ChEMBL963 ;
CompTox Dashboard (EPA)	DTXSID5023409 ;
ECHA InfoCard	100.000.873
Chemical and physical data
Formula	C17H19NO4
Molar mass	301.342 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C5;
	InChI 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 ; Key:UQCNKQCJZOAFTQ-ISWURRPUSA-N ;
	(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 abuse potential.^[8]

Oxymorphone 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]

^ "Drugs@FDA: FDA Approved Drug Products". www.accessdata.fda.gov. Retrieved 7 November 2017.
^ 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.
^ Hussain MA, Aungst BJ (August 1997). "Intranasal absorption of oxymorphone". Journal of Pharmaceutical Sciences. 86 (8): 975–976. doi:10.1021/js960513x. PMID 9269879.
^ ^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.
^ 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.
^ Sloan P (August 2008). "Review of oral oxymorphone in the management of pain". Therapeutics and Clinical Risk Management. 4 (4): 777–787. doi:10.2147/tcrm.s1784. PMC 2621383. PMID 19209260.
^ 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.
^ 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): 146–158. doi:10.1111/adb.12173. PMC 4383736. PMID 25130052.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. pp. 52X. ISBN 978-3-527-60749-5.
^ Wolf LK (19 June 2017). "FDA takes aim at opioid epidemic". Chemical & Engineering News. 95 (25): 8.
^ Office of the Commissioner (10 September 2019). "Press Announcements – FDA requests removal of Opana ER for risks related to abuse". www.fda.gov.
^ Bernstein L, Merle R (27 November 2019). "Six drug companies subpoenaed in federal opioids probe". The Washington Post. Retrieved 18 April 2020.

[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): 975–976. doi:10.1021/js960513x. PMID 9269879.

[Davis_2009-4] 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.

[FiresteinBudd2016-5] 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): 777–787. 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): 146–158. doi:10.1111/adb.12173. PMC 4383736. PMID 25130052.

[Fischer_2006-9] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. pp. 52X. ISBN 978-3-527-60749-5.

[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.

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