oxymorphone oxymorphone 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 potential to be abused. not to be confused with oxymorphazone. oxymorphoneclinical datatrade namesnumorphan, numorphone, opana, othersother names14-hydroxydihydromorphinoneahfs/drugs.commonographmedlineplusa610022license data us dailymed: oxymorphone routes ofadministrationby mouth, buccal, sublingual, intranasal, intravenous, epidural, subcutaneous, intramuscularatc coden02aa11 (who) legal statuslegal status au: s8 (controlled drug) ca: schedule i de: anlage ii (authorized trade only, not prescriptible) uk: class a us: schedule ii pharmacokinetic databioavailabilityby mouth: 10% buccal: 28% sublingual: 37.5% intranasal: 43%iv, im & it: 100%protein binding10%metabolismliver (cyp3a4, glucuronidation)elimination half-life7–9 hours duration of action: 6-8 hours orally, 4-6 hrs parenteral.excretionurine, fecesidentifiers iupac name 4,5α-epoxy-3,14-dihydroxy-17-methylmorphinan-6-one cas number76-41-5 ypubchem cid5284604iuphar/bps7094drugbankdb01192 ychemspider4447650 yunii9vxa968e0ckeggd08323 ychemblchembl963 ycomptox dashboard (epa)dtxsid5023409 echa infocard100.000.873 chemical and physical dataformulac17h19no4molar mass301.342 g·mol−13d model (jsmol)interactive image smiles cn1cc23c4c5ccc(o)c4o2c(=o)cc3(o)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 ykey:uqcnkqcjzoaftq-iswurrpusa-n y (verify) it 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. medical uses oxymorphone immediate release is indicated for the relief of moderate to severe pain, such as treatment of acute post surgical pain. for any chronic treatment of pain, clinicians should only consider long term use if there is significant clinical benefit to the patient's therapy that outweigh any potential risk. the first line treatment choices for chronic pain are non-pharmacological and non-opioid agents. oxymorphone extended-release tablets are indicated for the management of chronic pain and only for people already on a regular schedule of strong opioids for a prolonged period. immediate-release oxymorphone tablets are recommended for breakthrough pain for people on the extended-release version. compared to other opioids, oxymorphone has similar pain relieving efficacy. in the united states it is a schedule ii controlled substance with an acscn of 9652. oxymorphone er tablets should be taken on an empty stomach. availability brands and forms oxymorphone was marketed by endo pharmaceuticals, under the brand name(s) opana and opana er. opana er was withdrawn by the manufacturer in 2017 due to a fda request, making it unavailable in the us. however, both ir (immediate release) and er (extended release) formulations are still available under the generic name oxymorphone and oxymorphone er, provided by a multitude of different manufacturers. oxymorphone is also available as an injectable for inpatient use, available for iv (intravenous), im (intramuscular), and sc (subcutaneous) injection. an extended release (er) modified-release dosage form is commonly used, which modifies the pharmacokinetics of the drug. oral dosage forms oxymorphone comes in a variety of doses. ir tableter 12 hour tablet 5 mg5 mg 10 mg7.5 mg 10 mg 15 mg 20 mg 30 mg 40 mg special populations patients already suffering from debilitation are at a much higher risk of respiratory depression. nonopioid analgesics should be considered in this population. elderly patients are much more sensitive to adverse effects, such as falls, cognitive impairment and constipation, and should be monitored for such. decreased renal function associated with aging leads to decreased clearance of the drug, resulting in narrow therapeutic windows and increasing the danger of overdose. if oxymorphone is absolutely indicated, smaller initial doses should be started for this population. there is a risk of neonatal withdrawal symptom in the newborn if pregnant women take oxymorphone for a prolonged period. oxymorphone crosses the placenta and holds risk of birth defects, poor fetal growth, stillbirth, and preterm delivery. the children of mothers who are physically dependent on oxymorphone have a higher risk of similar dependence. due to these severe risks, oxymorphone is highly discouraged among this population. the amount of transfer of oxymorphone into the breast milk is not known and women are cautioned to weigh the risks and benefits before breastfeeding while on this medication. side effects the principal adverse effects of oxymorphone are similar to other opioids with constipation, nausea, vomiting, dizziness, dry mouth and drowsiness being the most common adverse effects. this drug is highly addictive as with other opioids and can lead to chemical dependence and withdrawal. overdose in common with other opioids, oxymorphone overdosage is characterized by respiratory depression, sleepiness progressing to stupor or coma, skeletal muscle weakness, cold and clammy skin, and sometimes slow heart rate and low blood pressure. in a severe case of overdose, apnea, circulatory collapse, cardiac arrest and death can occur. pharmacology pharmacodynamics oxymorphone elicits its effects by binding to and activating the μ-opioid receptor (mor) and, to a much lesser extent, the δ-opioid receptor (dor) and κ-opioid receptor (kor). its activity at the dor may augment its action at the mor. oxymorphone is 10 times more potent than morphine. the calculation of relative potency indicated that 1 mg of oxymorphone hydrochloride equaled 9.85 mg of morphine sulfate, or 1.02 mg of oxymorphone hydrochloride was equivalent to 10 mg of morphine sulfate. oxymorphone at opioid receptors affinities (ki)ratio mordorkormor:dor:kor 0.78 nm50 nm137 nm1:64:176 equianalgesic doses compoundroutedose codeinepo200 mg hydrocodonepo20–30 mg hydromorphonepo7.5 mg hydromorphoneiv1.5 mg morphinepo30 mg oxycodoneiv20 mg morphineiv10 mg oxycodonepo20 mg oxymorphonepo7–10 mg oxymorphoneiv1 mg pharmacokinetics