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Oxycodone

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Oxycodone.png
Oxycodone chemical structure


Oxycodone

4,5-α-epoxy-14-hydroxy-
3-methoxy-17-methyl-morphinan-6-one
CAS number
76-42-6
ATC code
N02AA05
Chemical formula C18H21NO4
Molecular weight 315.367
Bioavailability Up to 87% (PO)
Metabolism Hepatic
Elimination half-life 2-3 Hours
Excretion Urine
Pregnancy category B/D(prolonged use or in high doses at term)
Legal status DEA Schedule II
Routes of administration  ?

Oxycodone is a very powerful and potentially addictive opioid analgesic medication synthesized from thebaine. It is similar to codeine, but is more potent and has a higher dependence potential.

It is effective orally and is marketed in combination with aspirin (Percodan, Endodan, Roxiprin) or acetaminophen (Percocet, Endocet, Roxicet) for the relief of pain. It is also sold in a sustained-release form by Purdue Pharma under the trade name OxyContin and an instant-release form OxyIR. OxyContin is available in 10 mg, 20 mg, 40 mg, and 80 mg formulations, and, due to its sustained-release mechanism, is effective for eight to twelve hours. In the United States, oxycodone is a Schedule II controlled substance both as a single agent and in combination products containing acetaminophen or aspirin.

Chemical structure

The chemical structure of Oxycodone is the methylether of oxymorphone: 3-Methyl-oxymorphone. It could be also described as 14-Hydroxy-Codeinone.

Medical use

Oxycodone is one of the most powerful medications for pain control that can be taken orally. Percocet tablets (oxycodone with acetaminophen) are routinely prescribed for post-operative pain control. When used at recommended doses for relatively short periods (several weeks), it provides effective pain control with manageable side effects.

Constipation is the most frequently reported side effect, and occurs often enough that most physicians prescribe a laxative for use at the same time. Nausea is also common, requiring antiemetics.

Oxycodone is also used in treatment of moderate to severe chronic pain, particularly for cancer sufferers and individuals with severe back injury. Tolerance and physical dependence occurs after several months of treatment, with larger doses being required to achieve the same degree of analgesia.

According to the DEA and the companies that manufacture the drug, psychological addiction as a result of medical use is extremely rare. However, there are several lawsuits underway brought by plaintiffs who claim that they became addicted to the drug as a result of medical use.

Abuse

The introduction of OxyContin in 2000 resulted in increasing patterns of abuse. Unlike Percocet, whose potential for abuse is limited by the presence of acetaminophen, OxyContin contains only oxycodone and inert filler. Abusers crush the tablets to defeat the time-release mechanism, and have been reported to snort or inject the resulting powder to achieve rapid absorption into the bloodstream. It was once felt that "combination" opioids (those that contain one or more additional, non-narcotic ingredients) would be less subject to abuse, since, for example, the amount of acetaminophen present in large overdoses of Percocet would cause stomach upset and liver damage. However, it has been demonstrated that abusers seeking the euphoric "high" are not deterred by the gastrologic symptoms. Similar thinking also once motivated Canadian authorities to package oral methadone for use only in combination with Tang, an orange-flavored beverage powder. Surely they thought, nobody would be foolish enough to intravenously inject such a combination. The authorities were incorrect.

Oxycodone has similar effects to morphine and heroin, and appeals to the same abuse community. Armed robberies of pharmacies where the robber demanded only OxyContin, not cash, have occurred and seem to be on the rise. In some areas, particularly the eastern U.S., OxyContin has been the drug of greatest concern to enforcement authorities. Oxycodone abuse has been especially problematic in Appalachia; because of this, the drug has earned the nickname hillbilly heroin.

Because Oxycodone is highly regulated, when acquired illegally it is quite expensive. Street prices in Washington, DC, for example, have been reported to be anywhere from fifty cents to one dollar per milligram.

Like other opium derivatives, oxycodone is fatal at high doses or when combined with depressants such as alcohol. Several documented fatalities from OxyContin abuse have been made public.

On October 10, 2003, talk radio personality Rush Limbaugh made a public admission of addiction to prescription pain medication, including OxyContin, and announced his intention to pursue inpatient treatment. Also in 2003, singer/actress Courtney Love was arrested for OxyContin abuse.

Analgesics edit (http://search.academickids.com/encyclopedia/index.php?title=Template:Analgesics&action=edit)

{Paracetamol (acetaminophen) } {Tetrahydrocannabinol} {Cannabinoids} {Ketamine}

NSAIDs edit (http://search.academickids.com/encyclopedia/index.php?title=Template:NSAIDs&action=edit)

{Aspirin} {Celecoxib} {Diclofenac} {Ibuprofen} {Ketoprofen} {Ketorolac} {Naproxen} {Rofecoxib} {Indomethacin}

Opioids edit (http://search.academickids.com/encyclopedia/index.php?title=Template:Opioids&action=edit)

{Alfentanil} {Buprenorphine} {Carfentanil} {Codeine} {Codeinone} {Dextropropoxyphene} {Dihydrocodeine} {Endorphin} {Fentanyl} {Heroin} {Hydrocodone} {Hydromorphone} {Methadone} {Morphine} {Morphinone} {Oxycodone} {Oxymorphone} {Pethidine} {Remifentanil} {Sufentanil} {Tramadol}

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