oxymorphone

Also known as Opana®, oxymorphone hydrochloride, EN3202, 14-Hydroxydihydromorphinone, Dihydroxymorphinone, Oximorphonum, Dihydrohydroxymorphinone

Key facts

Drug.Watchedfields: changed
Drug.caption2: 3D representation of an oxymorphone molecule
Drug.class: Opioid
Drug.verifiedrevid: 456483627
Drug.IUPAC_name: 4,5α-Epoxy-3,14-dihydroxy-17-methylmorphinan-6-one
Drug.image: Oxymorphone.png
Drug.image_class: skin-invert-image
Drug.width: 170px
Drug.caption: Molecular structure of oxymorphone
Drug.image2: Oxymorphone 3D.png
Drug.image_class2: bg-transparent
Drug.tradename: Numorphan, Numorphone, Opana, others
Drug.MedlinePlus: a610022
Drug.DailyMedID: Oxymorphone
Drug.addiction_liability: High
Drug.routes_of_administration: By mouth, buccal, sublingual, intranasal, intravenous, epidural, subcutaneous, intramuscular
Drug.ATC_prefix: N02
Drug.ATC_suffix: AA11

via Wikipedia infobox

Chemical data

Formula: C17H19NO4
Molecular weight: 301.34 g/mol
IUPAC name: (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
SMILES: CN1CC[C@]23[C@@H]4C(=O)CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O
InChIKey: UQCNKQCJZOAFTQ-ISWURRPUSA-N
XLogP: 0.8
Polar surface area: 70 Å²
H-bond donors: 2
H-bond acceptors: 5
Formal charge: 0

via PubChem

Research

866 papers

Oxymorphone: a review.Supportive care in cancer : official journal of the Multinational Association of Supportive Care in Cancer · 2006
Oral oxymorphone for pain management.The Annals of pharmacotherapy · 2007
Oxymorphone and oxymorphone extended release: a pharmacotherapeutic review.Journal of opioid management · 2008
Ketorolac, Oxymorphone, Tapentadol, and Tramadol: A Comprehensive Review.Anesthesiology clinics · 2017
Clinical applications of oxymorphone.Journal of opioid management · 2013

via PubMed

Wikidata facts

Mass: 301.131

Show 5 more facts

chemical formula: C₁₇H₁₉NO₄
isomeric SMILES: CN1CC[C@]23[C@@H]4C(=O)CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O
canonical SMILES: CN1CCC23C4C(=O)CCC2(C1CC5=C3C(=C(C=C5)O)O4)O
Commons category: Oxymorphone
stylized name: oxyMORphone

Sources (5)

via Wikidata · CC0

~14 min read

Article

18 sections

Contents

Medical uses
Availability
Brands and forms
Oral dosage forms
Special populations
Side effects
Overdose
Pharmacology
Pharmacodynamics
Pharmacokinetics
Chemistry
History
Society and culture
Brand names
Abuse
Veterinary use
See also
References

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. The elimination half-life of oxymorphone is much faster intravenously, and as such, the drug is most commonly used orally. Like oxycodone, which metabolizes to oxymorphone, oxymorphone has a high abuse potential.

Oxymorphone was developed in Germany in 1914. It was patented in 1955 and approved for medical use in 1959. In June 2017 the FDA asked Endo Pharmaceuticals to remove its product from the US market. 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. Generic versions of extended-release oxymorphone, such as those manufactured by Amneal Pharmaceuticals, are still available in the US.