Oxymorphone
Systematic (IUPAC) name
4,5α-epoxy-3,14-dihydroxy- 17-methylmorphinan-6-one
Identifiers
CAS number	76-41-5
ATC code	N02A
PubChem	5284604
DrugBank	APRD00158
Chemical data
Formula	C17H19NO4
Mol. mass	301.337 g/mol
Physical data
Melt. point	248–249 °C (Expression error: Unrecognised punctuation character "�" °F)
Pharmacokinetic data
Bioavailability	10% (oral)
Metabolism	hepatic
Half life	1.3 (+/-0.7) hours
Excretion	?
Therapeutic considerations
Pregnancy cat.	C(US) Image File history File links Oxymorphone. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, symbol, number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, period, block 16, 2, p Appearance colorless (gas) pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... For other uses of terms redirecting here, see US (disambiguation), USA (disambiguation), and United States (disambiguation) Motto In God We Trust(since 1956) (From Many, One; Latin, traditional) Anthem The Star-Spangled Banner Capital Washington, D.C. Largest city New York City National language English (de facto)1 Demonym American...
Legal status	Schedule I(CA) Class A(UK) Schedule II(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Controlled Drugs and Substances Act is Canadas federal drug control statute. ... Motto (Latin for From Sea to Sea) Anthem O Canada Royal anthem: God Save the Queen Capital Ottawa Largest city Toronto Official languages English, French Government Parliamentary democracy and federal constitutional monarchy  -  Monarch Queen Elizabeth II  -  Governor General Michaëlle Jean  -  Prime Minister Stephen Harper Establishment  -  Act of Union February... The Misuse of Drugs Act 1971 is an Act of Parliament, by which the United Kingdom aims to control the possession and supply of numerous drugs and drug-like substances, as listed under the Act, and to enable international co-operation against illegal drug trafficking. ... The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... For other uses of terms redirecting here, see US (disambiguation), USA (disambiguation), and United States (disambiguation) Motto In God We Trust(since 1956) (From Many, One; Latin, traditional) Anthem The Star-Spangled Banner Capital Washington, D.C. Largest city New York City National language English (de facto)1 Demonym American...
Dependence Liability	High
Routes	intravenous, intramusucular, subcutaneous, oral, rectal

Oxymorphone (Opana, Numorphan) or 14-Hydroxydihydromorphinone is a powerful semi-synthetic opioid analgesic that is derived from thebaine, and is approximately 6–8 times more potent than morphine. Clinically, it is administered as its hydrochloride salt via injection, or suppository; typically in dosages of 1 mg (injected) to 5 mg (suppository). Endo Pharmaceuticals markets oxymorphone in the United States as Opana and Opana ER. Opana is available as 5 mg and 10 mg tablets; Opana ER, an extended-release form of oxymorphone, is available as tablets in strengths of 5 mg, 10 mg, 20 mg, and 40 mg. As with other opioids, oxymorphone can cause physical dependency, and has the potential for abuse. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... Morphinone is a very strong Opiod. ... An opioid is a chemical substance that has a morphine-like action in the body. ... An analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain (achieve analgesia). ... A minor constituent of opium, thebaine or paramorphine (C19H21NO3) is chemically similar to both morphine and codeine, but produces stimulatory rather than depressant effects. ... This article is about the drug. ... In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (mostly amines). ... Four 500mg acetaminophen/paracetamol suppositories A suppository is a medicine that is inserted either into the rectum (rectal suppository) or into the vagina (vaginal suppository) where it melts. ... Endo became Endo Pharmaceuticals Inc. ... An opioid is any agent that binds to opioid receptors found principally in the central nervous system and gastrointestinal tract. ... Addiction is a compulsion to repeat a behaviour regardless of its consequences. ... Comparison of the perceived harm for various psychoactive drugs from a poll among medical psychiatrists specialized in addiction treatment[1] This article is an overview of the nontherapeutic use of alcohol and drugs of abuse. ...

Uses

Oxymorphone is indicated for the relief of moderate to severe pain and also as a preoperative medication to alleviate apprehension, maintain anesthesia, and as an obstetric analgesic. Additionally, it can be used for the alleviation of pain in patients with dyspnea associated with acute left ventricular failure and pulmonary edema.

Opana® extended-release tablets are indicated for the management of chronic pain of all or most aetiologies and are indicated only for patients already on a regular schedule of strong opioids for a prolonged period. The immediate-release Opana® tablets are recommended for management of breakthrough pain for patients on the extended-release version.

Physical characteristics

Oxymorphone HCl occurs as odorless white crystals or white to off-white powder. It will darken in color with prolonged exposure to light. One gram of oxymorphone is soluble in 4 ml of water and it is slightly soluble in alcohol and ether. The commercially available injection has a pH of 2.7–4.5.

Toxicity

In common with other opioids, oxymorphone overdosage is characterized by respiratory depression, extreme somnolence progressing to stupor or coma, skeletal muscle flaccidity, cold and clammy skin, and sometimes bradycardia and hypotension. In a severe case of overdose, apnea, circulatory collapse, cardiac arrest, and death may occur.

At equianalgesic doses oxymorphone is marginally more toxic than morphine but less so than fully synthetic opioids such as methadone and pethidine. At therapeutic doses, toxicity is primarily manifested as miosis, nausea, and possibly occasional mild involuntary muscle movements especially in the distal portions of the extremities and the shoulder area in some cases. This is most common in patients taking a number of other drugs for their condition, especially muscle relaxants and some adjuvant analgesics, and also appears to happen most often during and immediately after a significant upward titration in the single-dose and per 24 hour doses.

Instances of the body suddenly jerking bolt upright from a more relaxed sitting position is a sign of high and/or rapidly increasing serum levels of opioids and all of the above movements are likely due to the anticholinergic or anticholinergic-like effects of opioids and/or other medications prescribed at the same time, as they manifest in patients on atropine-like drugs as well. The primary risk here involves dropping objects, spilling liquids, striking body parts against walls, and potentially losing footing on flat ice surfaces.

While all this can be frightening at first, more than 85 percent of patients do not experience it at any time during treatment, and oxymorphone does not appear to induce seizures in neurologically healthy patients as does the pethidine series of opioids (pethidine, anileridine, alphaprodine, piminodine and others) nor does it have toxic metabolites which accumulate in the system as do the pethdine and methadone families of synthetic opioids. There is also no real evidence that oxymorphone significantly lowers the seizure threshold as do tramadol and some of the other synthetics mentioned above.

Brand Names

• Numorphan (suppository and injectable solution)
• Opana (tablet)
• Opana ER (extended-release tablet)

Other manufacturers and Endo themselves have also, according to reports in the mass media and professional journals over the last few years, are considering and/or currently developing a Duragesic®-style oxymorphone skin plasters and oxymorphone and hydromorphone nasal sprays.

Illicit Use

Until its removal from the United States market in the early 1970s, oxymorphone in the form of Numorphan 10 mg instant-release tablets was one of the most sought-after and well-regarded opioids of the IV drug using community. Known popularly as "blues" for their light blue color, the tablets contained very few insoluble binders—making them easy to inject—and were extremely potent when used intravenously. "Blues" were also considered to be especially euphoric; comparable to or better than heroin. Numorphan tablets, and the oxymorphone they contained, are the "blues" referred to in the film Drugstore Cowboy. Intravenous therapy or IV therapy is the giving of liquid substances directly into a vein. ... Drugstore Cowboy is a 1989 film written and directed by Gus Van Sant. ...

Oxymorphone is not a component of "T's and blues", 1970s slang for a combination of pentazocine ("T's") and pyribenzamine ("blues"). Pentazocine is a synthetically-prepared narcotic (opioid analgesic) drug used to treat mild to moderately severe pain. ... Pentazocine is a synthetically-prepared narcotic (opioid analgesic) drug used to treat mild to moderately severe pain. ... Tripellenamine (Pyribenzamine) is a first generation antihistamine. ...

The low bioavailability of oxymorphone after oral administration requires Opana® extended-release to contain up to 40 mg of oxymorphone per tablet -- almost as much as an entire case of Numorphan® ampoules; attempts to circumvent the extended-release mechanism by injecting or snorting the tablets are therefore particularly dangerous.

Chemistry

Oxymorphone is commercially produced from thebaine, which is a minor constituent of the opium poppy (Papaver somniferum) but thebaine is found in greater abundance (3%) in the roots of the oriental poppy (Papaver orientale). Oxymorphone can also be synthesized from morphine or oxycodone, and is an active metabolite of the latter drug. The structure-activity relationship of oxymorphone and its derivatives has been well-examined. Esterification of the hydroxyl groups yields stronger compounds. The acetyl ester is 2.5 times more potent and the propenyl ester six times more potent than the parent compound. If the 14-hydroxyl group is formed into the cinnamyl ester, the product is 114 times more potent. The most powerful oxymorphone derivative known is the 14-cinnamyl 3-acetyl ester, which is over 200 times more potent than morphine.^[1] A minor constituent of opium, thebaine or paramorphine (C19H21NO3) is chemically similar to both morphine and codeine, but produces stimulatory rather than depressant effects. ... Binomial name L. The opium poppy, Papaver somniferum, is the type of poppy from which opium and all refined opiates such as morphine, thebaine, codeine, papaverine, and noscapine are extracted. ... Binomial name Papaver orientale (L.) The Oriental poppy (Papaver orientale) is a perennial poppy of the genus Papaver. ... Not to be confused with oxytocin. ... Quantitative structure-activity relationship (QSAR) is the process by which chemical structure is quantitatively correlated with a well defined process, such as biological activity or chemical reactivity. ... Esterification is the general name for a chemical reaction in which two chemicals (typically an alcohol and an acid) form an ester as the reaction product. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... Acetyl is the radical of acetic acid. ... Propenyl is a chemical radical of propene (propylene). ...

See also

• Opioids
• Hydromorphone
• Oxycodone
• Drug addiction

An opioid is any agent that binds to opioid receptors found principally in the central nervous system and gastrointestinal tract. ... Hydromorphone is a drug developed in Germany in the 1920s and introduced to the mass market beginning in 1926. ... Not to be confused with oxytocin. ... Drug addiction, or dependency is the compulsive use of drugs, to the point where the user has no effective choice but to continue use. ...

References

1. ^ J Exp Ther. Pharm. (1964) 174–182.

External links