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Oxycodone (Molecule of the Month for June 2007)

Percodan, Endodan, Roxiprin, Percocet, Endocet, Roxicet, Tylox, Combunox

Oxycodone is an opioid analgesic medication synthesized from thebaine. Its name is derived from codeine. It is effective orally and is marketed in combination with aspirin (Percodan, Endodan, Roxiprin) or paracetamol/acetaminophen (Percocet, Endocet, Roxicet, Tylox) for the relief of pain. More recently, ibuprofen has been added to oxycodone (Combunox). In the United States, oxycodone is a Schedule II controlled substance both as a single agent and in combination with products containing acetaminophen, ibuprofen or aspirin.

Percocet tablets (oxycodone with acetaminophen) are routinely prescribed for post-operative pain control. Oxycodone is also used in treatment of moderate to severe chronic pain. There is no evidence that oxycodone is more effective than any other opioid, and, in palliative care, morphine remains the gold standard. However, it can be useful as an alternative opioid if a patient has troublesome adverse effects with morphine.

Oxycodone was first synthesized in a German laboratory in 1916, a few years after the German pharmaceutical company Bayer had stopped the mass production of heroin due to addiction and abuse by both patients and physicians. It was hoped that a thebaine-derived drug would retain the analgesic effects of morphine and heroin with less of the euphoric effect which led to addiction and over-use. The introduction of OxyContin in 1995 resulted in increasing patterns of abuse. The discovery of its recreational benefits has led to an illicit underground market. Due to acts such as pharmacy diversion and "doctor shopping", the drug is widely available to those without a prescription. The increased misuse of the drug has led to a higher number of emergency department mentions and deaths associated with oxycodone. Between 1994 and 2001, there was a reported 352% increase in ER visits related to all forms of oxycodone usage. This is possibly in part due to the availability of OxyContin beginning in 1995. Despite the increased efforts by the FDA, DEA, and state/local authorities, negative publicity of the drug is not stopping its illicit use, but instead seems to be fueling the underground market. The OxyContin tablets that are most commonly diverted and abused are the 40mg tablets, which sell on the black market for approximately $15-40 per tablet. Abusers either insufflate (snort), inject, chew, or smoke the tablets - as these methods of consumption destroy the built-in time release and give the user all of the drug at once, resulting in a euphoric and blissful rush; however, this can be dangerous, as far more oxycodone is released than is medically safe.

Formal Chemical Name (IUPAC)
4, 5-epoxy-14-hydroxy-3- methoxy-17-methylmorphinan-6-one



Picture of Oxycodone 3D model

click on the picture of  Oxycodone above to interact
with the 3D model of the
Oxycodone structure
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Picture of Oxycodone

C18 H21 N O4

Update by Karl Harrison
(Molecule of the Month for June 2007 )

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