Oxycodone ~ From Wikipedia, the free encyclopedia

Posted: September 8, 2010 in Uncategorized

Not to be confused with oxytocin, oxandrolone, hydrocodone, or oxazepam.
Oxycodone
Systematic (IUPAC) name
(5R,9R,13S,14S)-4,5α-epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
Identifiers
CAS number 76-42-6
ATC code N02AA05
N02AA55 (in combinations)
PubChem CID 5284603
DrugBank DB00497
ChemSpider 4447649
Chemical data
Formula C18H21NO4
Mol. mass 315.364 g/mol
SMILES eMolecules & PubChem
Synonyms dihydrohydroxycodeinone, 14-hydroxydihydrocodeinone, 6-deoxy-7,8-dihydro-14-hydroxy-3-O-methyl-6-oxomorphine[1]
Pharmacokinetic data
Bioavailability Up to 87%
Protein binding 45%
Metabolism Hepatic (CYP450: 2D6 substrate)
Half-life 3 – 4.5 hr
Excretion Urine (19% unchanged)
Therapeutic considerations
Pregnancy cat. B/D (prolonged use or in high doses at term)
Legal status Controlled (S8) (AU) Schedule I (CA) ? (UK) Schedule II (US)
Dependence Liability Moderate – High
Routes oral, intramuscular, intravenous, intranasal, subcutaneous, transdermal, rectal, epidural[2]
YesY(what is this?) (verify)

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 in an attempt to improve on the existing opiates: morphine, diacetylmorphine (heroin), and codeine.[2]

Oxycodone oral medications are generally prescribed for the relief of moderate to severe pain. Currently it is formulated as single ingredient products or compounded products. Some common examples of compounding are oxycodone with acetaminophen/paracetamol or NSAIDs such as ibuprofen. The formulations are available as generics but are also made under various brand names.

OxyContin is Purdue Pharma’s brand for time-release single-ingredient oxycodone oral medication. The manufacturing rights to time-released generic oxycodone are under dispute.

Contents

History

Freund and Speyer of the University of Frankfurt in Germany first synthesized oxycodone from thebaine in 1916,[9] 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.[6] It was first introduced to the US market in May 1939..

The International Narcotics Control Board estimates that 11.5 tons[clarification needed] of oxycodone were manufactured worldwide in 1998, which grew to 75.2 tons in 2007.[10] Of all countries, the United States had the highest total consumption of oxycodone in 2007 (82% of the world total of 51.6 tons).[10] In addition, in 2007 the U.S. had the highest per capita consumption of oxycodone, followed by Canada, Denmark, Australia, and Norway.[10]

Clinical use

In a 2008 review written by authors who “are members of advisory boards and speaker panels for Mundipharma,” prolonged-release oxycodone (i.e., OxyContin) was found to be superior to placebo in randomized controlled trials concerning diabetic neuropathy, postherpetic neuralgia, osteoarthritis, ambulatory laparoscopic tubal ligation surgery, unilateral total knee arthroplasty, and abdominal/gynaecological surgery.[47]

In 2001, the European Association for Palliative Care recommended that oral hydromorphone or oxycodone, “if available in both normal release and modified release formulations for oral administration,” be second-line alternatives to oral morphine for cancer pain.[48] There is no evidence that any opioids are superior to morphine in relieving the pain of cancer, and no controlled trials have shown oxycodone to be superior to morphine.[49] However, switching to an alternative opioid can be useful if adverse effects are troublesome, although the switch can be in either direction, i.e. some patients have fewer adverse effects on switching from morphine to oxycodone and vice versa.

Illicit use and diversion

Canada

A study at St. Michael’s Hospital and the Institute for Clinical Evaluative Sciences (ICES) in Toronto, found that deaths from opioid pain relievers nearly doubled from 13.7 deaths per million residents in 1991 to 27.2 deaths per million residents in 2004.[72]

United States

Instances of recreational use and diversion of OxyContin have increased in the U.S. beginning in the late 1990s.[73] The slang term hillbilly heroin for OxyContin refers to the occurrence of the “earliest reported cases of Oxycontin abuse” in the U.S. in rural areas such as Appalachia.[74] Diversion of OxyContin in the U.S. may occur through “fraudulent prescriptions, doctor shopping, over-prescribing, and pharmacy theft.”[73]

A 2003 study by the Government Accountability Office found four factors that may have contributed to the illicit use and distribution of OxyContin in the U.S.:[11]

  • OxyContin contains a large amount of oxycodone compared with other types of oxycodone containing pills.
  • OxyContin’s warning label said to not crush the controlled-release tablets because of the potential for rapid release of oxycodone, which led to many people crushing the tablets and injecting or snorting the drug.
  • By 2001, sales of OxyContin in the U.S. exceeded $1 billion per year.
  • People who received prescriptions for OxyContin from across the United States and almost all socioeconomic status have perceived a “profit potential” in selling the pills to drug dealers (e.g., 20 mg of OxyContin could be bought for $2 but sold for $5-20)[citation needed].

A study published in 2005 examined the prevalence of opiate analgesic use among “recreational drug users and street addicts” as perceived by “key informants”[who?] throughout the U.S.; the authors found that non-clinical use of opiates was increasing in general, but that of the drugs studied use of OxyContin “was mentioned most frequently.”[75] Purdue Pharma has attempted to reformulate the 10–40 mg strengths of OxyContin to prevent the release of a high percentage of the oxycodone by crushing; however, in 2008 a joint panel convened by the U.S. Food and Drug Administration was “concerned that abusers could find a way to manipulate the new formulation.”[76]

One investigation in Boston found that OxyContin was a “gateway” drug for heroin, which addicts turned to as cheaper alternative.[77]

Other countries

The illegal use of OxyContin began in Australia in the early 2000s. By 2007, 51% of a national sample of injection drug users in Australia had reported using oxycodone, and 27% had injected it in the last six months.[78]

Hazardous use, harmful use, and diversion of OxyContin in the U.K. commenced in the early- to mid-2000s.[79] The first known death due to OxyContin overdose in the U.K. occurred in 2002.[80]

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