Oxycodone
From DrugPedia: A Wikipedia for Drug discovery
| Oxycodone
| |
| Systematic (IUPAC) name | |
| N/A | |
| Identifiers | |
| CAS number | ? |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C18H21NO4 |
| Mol. mass | 315.36364 |
| SMILES | & |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | ? |
Contents |
[edit] Description
Semisynthetic derivative of CODEINE that acts as a narcotic analgesic more potent and addicting than codeine.
Oxycodone is an opioid analgesic medication synthesized from opium-derived thebaine. It was developed in 1916 in Germany, as one of several new semi-synthetic opioids with several benefits over the older traditional opiates and opioids; morphine, diacetylmorphine (heroin) and codeine.
Currently it is best known as the main active ingredient in a number of oral medications commonly prescribed for the relief of moderate to severe pain. Oxycodone can be combined with inert binders (e.g., OxyContin); with paracetamol, also known as acetaminophen (e.g., Percocet, Endocet, Tylox, and Roxicet); with aspirin (e.g., Percodan, Endodan, Roxiprin); and with ibuprofen (Combunox). Of the oral medications containing oxycodone, OxyContin is notable for its sales; for controversies concerning its patent status and marketing; and for its potentials for hazardous use, harmful use, dependence, and diversion.
[edit] Chemistry and nomenclature
Oxycodone's chemical name is derived from codeine. The chemical structures are very similar, differing only in that
Oxycodone has a hydroxyl group at carbon-14 (codeine has just a hydrogen in its place), hence oxycodone; Oxycodone has a 7,8-dihydro feature, whereas codeine has a double bond between those two carbons; and Oxycodone has a carbonyl group (as in ketones) in place of the hydroxyl group of codeine, hence the "-one" suffix.
It is also similar to hydrocodone, differing only in that it has a hydroxyl group at carbon-14. The synonyms for oxycodone in the academic literature include "dihydrohydroxycodeinone," "Eucodal," "Eukodal," "14-hydroxydihydrocodeinone," and "Nucodan." In a UNESCO convention, the translations of "oxycodone" are oxycodone (French), oxicodona (Spanish), والأوآسيكودون (Arabic), 羟考酮 (Chinese), and оксикодон (Russian). The word "oxycodone" should not be confused with "oxandrolone," "oxazepam," "oxybutynin," "oxytocin," "Roxanol," or "Roxicet."
[edit] History
Freund and Speyer of the University of Frankfurt in Germany first synthesized oxycodone from thebaine in 1916, a few years after the German pharmaceutical company Bayer had stopped the mass production of heroin due to hazardous use, harmful use, and dependence. It was hoped that a thebaine-derived drug would retain the analgesic effects of morphine and heroin with less dependence. To some extent this was achieved, as oxycodone does not have the same immediate effect as heroin or morphine nor does it last as long.
The first clinical use of the drug was documented in 1917. It was first introduced to the US market in May 1939.
The International Narcotics Control Board estimates that 11.5 tons of oxycodone were manufactured worldwide in 1998, which grew to 75.2 tons in 2007. Of all countries, the United States had the highest total consumption of oxycodone in 2007 (82% of the world total of 51.6 tons). In addition, in 2007 the U.S. had the highest per capita consumption of oxycodone, followed by Canada, Denmark, Australia, and Norway.
[edit] OxyContin
OxyContin is the brand name of a time-release formula of oxycodone produced by the pharmaceutical company Purdue Pharma. It was approved by the U.S. Food and Drug Administration in 1995 and first introduced to the U.S. market in 1996. By 2001, OxyContin was the best-selling non-generic narcotic pain reliever in the U.S.; in 2002, over 7.2 million prescriptions were written for it, for total sales of $1.5 billion. An analysis of data from the U.S. Drug Enforcement Administration found that retail sales of oxycodone "jumped nearly six-fold between 1997 and 2005." Mundipharma distributes OxyContin in Australia, China, and Europe.
OxyContin is available in 5 mg (blue) tablets in Canada and the U.K.; 10 mg (white) in Canada, the U.S., and the U.K.; 15 mg (grey) in the U.S.; 20 mg (pink) in Canada, the U.S., and the U.K.; 30 mg (brown) in the U.S.; 40 mg (yellow) in Canada, the U.S., and the U.K.; 60 mg (red) in the U.S.; and 80 mg (green) in Canada, the U.S., and the U.K. In 2001, Purdue Pharma suspended distribution of 160 mg tablets in the U.S. because of the "possibility of illicit use of tablets of such high strength."
Slang terms for OxyContin include "Hillbilly Heroin," "Killers," "OC," "Oxy," and "Oxycotton." The word "OxyContin" should not be confused with "morphine sulfate," "MS Contin," "Oxandrin," "oxybutynin," "oxytocin," or "Roxicodone."
[edit] Lawsuits concerning generic OxyContin
Purdue has multiple patents for OxyContin, but has been involved in a series of ongoing legal battles on the validity of these patents. On June 7, 2005, the United States Court of Appeals for the Federal Circuit upheld a decision from the previous year that some of Purdue’s patents for OxyContin could not be enforced. This decision allowed and led to the immediate announcement from Endo Pharmaceuticals that they would begin launching a generic version of all four strengths of OxyContin. Purdue, however, had already made negotiations with another pharmaceutical company (IVAX Pharmaceuticals) to distribute their brand OxyContin in a generic form. This contract was severed, and as of October 2005 Watson Pharmaceuticals became the exclusive U.S. distributor of Purdue-manufactured generic versions of OxyContin tablets in 10, 20, 40, and 80 milligram dosages.
[edit] Marketing and misbranding
Critics have accused Purdue Pharma of putting profits ahead of public interest by applying "significant political pressure" to attempt to reverse South Carolina's requiring prior approval before a person with Medicaid can receive the drug; for "fail[ing] to adequately warn consumers of the risks" of OxyContin such as dependence; and for promoting the drug "aggressively" and by means such as "promotional beach hats, pedometers and swing-music CDs."
In May 2007 Purdue Pharma "agreed to pay $19.5 million" in fines relating to aggressive off-label marketing practices of OxyContin in 26 states and the District of Columbia. In specific, the company encouraged dosing more frequent than the recommended interval of 12 hours, and did not fully disclose the risk of hazardous or harmful use.
Later in May 2007 Purdue Pharma and three of its top executives pleaded guilty in a Virginia federal court to charges that they misbranded OxyContin by representing it to have "less euphoric effect and less abuse potential" than it actually has, and by claiming that people taking the drug at low doses could stop taking it suddenly without symptoms of withdrawal. The FDA had not approved these claims. The company and the executives were to pay $634 million in fines for felony and misdemeanor misbranding.
In October 2007, officials in Kentucky filed a lawsuit against Purdue Pharma for misleading health care providers and consumers "regarding the appropriate uses, risks and safety of OxyContin"; as of mid-2008, however, the case had been "consolidated with other lawsuits into a single multi-litigation suit" in a federal court in New York.
On February 1, 2006, the Federal Circuit Court of Appeals issued a decision revising its June 7, 2005, decision. This time the court vacated the lower court's "judgment that the patents-in-suit are unenforceable due to inequitable conduct," and the case was "remanded for further proceedings."
Purdue Pharma has since announced resolution of its infringement suits with Endo, Teva, IMPAX,[ and Mallinckrodt. Endo and Teva each agreed to cease selling generic forms of OxyContin. IMPAX negotiated a temporary, and potentially renewable, license. In 2008, Mallinckrodt Pharmaceuticals reintroduced generic OxyContin in the strengths of 10 mg, 20 mg, 40 mg and 80 mg, which was made possible by a temporary royalties-bearing license with Purdue Pharma that expires in 2009.
[edit] General Properties
*Molecular Weight
315.36364
*Molecular Formula
C18H21NO4
*IUPAC NAME
N/A
*Canonical Smiles
CN1CCC23C4C(=O)CCC2(C1CC5=C3C(=C(C=C5)OC)O4)O
*Isomeric Smiles
CN1CC[C@]23C4C(=O)CCC2([C@H]1CC5=C3C(=C(C=C5)OC)O4)O
*XLogP
0.3
*Topological Polar Surface Area
59
