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Oxycodone is made, commercially, from thebaine, an opiate alkaloid and minor component of opium[3]. The 14′ hydroxy group increases potency by about 50% over hydrocodone.[citation needed]
The chemical structure of oxycodone is the methylether of oxymorphone: 3-methyl-oxymorphone. It could also be described as 14-hydroxy-7,8-dihydro-codeinone. It is principally supplied as its hydrochloride salt: oxycodone hydrochloride. The terephtalate salt of oxycodone is present in some formulations such as Percodan as 7.6 per cent of the weight of the oxycodone salts content of the product, viz. 5 mg of oxycodone in Percodan is 4.62 mg hydrocloride and 0.38 mg terephtlalate. There does not appear to be a significant difference in the action of the salts. The hydrochloride-terephtalate mixture appears to be part of the original formulation of Percodan by its German manufacturers from more than 75 years ago.[citation needed]
Other oxycodone salts used around the world include the phosphate, sulphate, pectinate, tartrate, bitartrate, citrate and iodide.
Oxycodone can be administered orally, intranasally, via intravenous/intramuscular/subcutaneous injection, or rectally. The bioavailability of intranasal administration averages 60-87%, with rectal administration yielding the same results. Injecting oxycodone will result in a stronger effect and quicker onset.[4] Similar to codeine and hydrocodone, oxycodone requires demethylation by the cytochrome CYP2D6 enzyme in order to become activated and any analgesic effect to occur .[5]
Two 5mg oxycodone/APAP tablets
Oxycontin tablets of varying dose
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. Both immediate-release and sustained-release oxycodone are now available (OxyNorm and OxyContin in the UK). There are no comparative trials showing that oxycodone is more effective than any other opioid.[6] In palliative care, morphine remains the gold standard.[7] However, it can be useful as an alternative opioid if a patient has troublesome adverse effects with morphine.
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). It is also sold in a sustained-release form by Mundipharma, and in the US by Purdue Pharma under the trade name OxyContin (the name is actually short for Oxycodone Continuous release) as well as generic equivalents, and instant-release forms Endone, OxyIR, OxyNorm, Percolone, OxyFAST, Supeudol, and Roxicodone. OxyNorm is available in 5, 10 and 20mg gelcapsules, and favoured among IV injecting opioid users because they contain only 2 inert binders, buth unsoluble, making it easy to prepare them for injection. OxyNorm is also available as 10mg/ml concentrated liquid in 100ml bottles in some countries, and OxyNorm 1ml injection ampoules of 10mg/ml are currently in their trial stage by the CFK. Roxicodone is available in 20 (white), 40 (green), and 80 (light blue) mg tablets. OxyContin was briefly available in: 5 (white), 10 (white), 15 (pink), 20 (pink), 30 (yellow), 40 (yellow), 45 (yellow), 60 (beige), 80 (green) and 160 (blue) mg tablets.[8] (although note that not all of these dosages are marketed in the USA) and, due to its sustained-release mechanism, is effective for eight to twelve hours. The 160 mg tablets were removed from sale due to problems with overdose, but have been re-introduced for limited use under strict medical supervision. On October 18, 2006, the FDA gave approval for three new dosage strengths, 15mg, 30mg, and 45mg.[9] OxyNorm is available in 5, 10, and 20 mg capsules and tablets; also as a 1 mg/1 ml liquid in 250 ml bottles and as a 10 mg/1 ml concentrated liquid in 100 ml bottles. Available in Europe and other areas outside the United States, Proladone® suppositories contain 15 mg of oxycodone pectinate and other suppository strengths under this and other trade names are less frequently encountered. Injectable oxycodone hydrochloride or tartrate is available in ampoules and multi-dose phials in many European countries and to a lesser extent various places in the Pacific Rim. For this purpose, the most common trade names are Eukodol and Eucodol.
Nausea, drowsiness, constipation, lightheadedness, rash or itchiness, dizziness, and emotional mood disorders are the most frequently reported side effects. Other side effects can also include dry mouth and slightly decreased testosterone levels in men. Oxycodone accumulates in patients with renal or liver impairment, and dose reductions may be needed.
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