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Encyclopedia > Oxycodone
Oxycodone
Systematic (IUPAC) name
4, 5-epoxy-14-hydroxy-3- methoxy-17-methylmorphinan-6-one
Identifiers
CAS number 76-42-6
ATC code N02AA05
PubChem 5284603
DrugBank APRD00387
Chemical data
Formula C18H21NO4 
Mol. mass 315.364 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability Up to 87%
Protein binding 45%
Metabolism Hepatic (CYP450: 2D6 substrate)
Half life 3 - 4.5 hours
Excretion Urine (19% unchanged)
Therapeutic considerations
Pregnancy cat.

B/D (prolonged use or in high doses at term) Image File history File links Mergefrom. ... Percodan® is a potent opioid painkiller used to treat moderately severe to severe acute (short-term) pain. ... Oxytocin (Greek: quick birth) is a mammalian hormone that also acts as a neurotransmitter in the brain. ... Image is drawn in bkchem and GIMP. This image has been released into the public domain by the copyright holder, its copyright has expired, or it is ineligible for copyright. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula is an easy way of expressing information about the atoms that constitute a particular chemical compound. ... For other uses, see Carbon (disambiguation). ... This article is about the chemistry of hydrogen. ... General Name, symbol, number nitrogen, N, 7 Chemical series nonmetals Group, period, block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... This article is about the chemical element and its most stable form, or dioxygen. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The biological half-life of a substance is the time required for half of that substance to be removed from an organism by either a physical or a chemical process. ... The kidneys are important excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status

Controlled (S8)(AU) Schedule I(CA) Class A(UK) Schedule II(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. ... For other uses, see Australia (disambiguation). ... The Controlled Drugs and Substances Act is Canadas federal drug control statute. ... Motto (Latin for From Sea to Sea) Anthem O Canada Royal anthem: God Save the Queen Capital Ottawa Largest city Toronto Official languages English, French Government Parliamentary democracy and federal constitutional monarchy  -  Monarch Queen Elizabeth II  -  Governor General Michaëlle Jean  -  Prime Minister Stephen Harper Establishment  -  Act of Union February... The Misuse of Drugs Act 1971 is an Act of Parliament, by which the United Kingdom aims to control the possession and supply of numerous drugs and drug-like substances, as listed under the Act, and to enable international co-operation against illegal drug trafficking. ... This box:      The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... For other uses of terms redirecting here, see US (disambiguation), USA (disambiguation), and United States (disambiguation) Motto In God We Trust(since 1956) (From Many, One; Latin, traditional) Anthem The Star-Spangled Banner Capital Washington, D.C. Largest city New York City National language English (de facto)1 Demonym American...

Dependence Liability Moderate - High
Routes Oral, intramuscular, intravenous, intranasally, subcutaneous, transdermal, rectal

Oxycodone is an opioid analgesic medication synthesized from 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 and codeine. It was introduced to the pharmaceutical market as Eukodal or Eucodal and Dinarkon. Its chemical name is derived from codeine - the chemical structures are very similar, differing only in that the hydroxyl group of codeine has been oxidized to a carbonyl group (as in ketones), hence the "-one" suffix, the 7,8-dihydro-feature (codeine has a double-bond between those two carbons), and the hydroxyl group at carbon-14 (codeine has just a hydrogen in its place), hence oxycodone. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body. ... An opioid is a chemical substance that has a morphine-like action in the body. ... An analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain (achieve analgesia). ... This article does not cite any references or sources. ... A minor constituent of opium, thebaine or paramorphine (C19H21NO3) is chemically similar to both morphine and codeine, but produces stimulatory rather than depressant effects. ... This article is about the drug. ... Diacetylmorphine (INN), diamorphine (BAN), or more commonly heroin, is a semi-synthetic opioid. ... For the band, see Codeine (band). ...


In the United States, oxycodone is a Schedule II controlled substance both as a single agent and in combination with products containing paracetamol (aka acetaminophen), ibuprofen or aspirin. It was first introduced to the US market in May 1939 and is the active ingredient in a number of pain medications commonly prescribed for the relief of moderate to heavy pain, either with inert binders (oxycodone, OxyContin) or supplemental analgesics such as acetaminophen (Percocet,Endocet, Tylox, Roxicet) and aspirin (Percodan, Endodan, Roxiprin ). It is also sold in a sustained-release form by Mundipharma, and in the United States by Purdue Pharma under the trade name OxyContin (Oxycodone Continuous release) as well as generic equivalents, and instant-release forms Endone, OxyIR, OxyNorm, Percolone, OxyFAST, Supeudol, and Roxicodone. More recently, ibuprofen has been added to oxycodone (Combunox). This box:      The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... Paracetamol (INN) (IPA: ) or acetaminophen (USAN), is the active metabolite of phenacetin, a so-called coal tar analgesic. ... Acetaminophen (USAN) or paracetamol (INN), is a popular analgesic and antipyretic drug that is used for the relief of fever, headaches, and other minor aches and pains. ... Coated 200 mg ibuprofen tablets Ibuprofen (INN) (IPA: ) (from the earlier and no longer correct nomenclature iso-butyl-propanoic-phenolic acid) is a non-steroidal anti-inflammatory drug (NSAID) originally marketed as Brufen, and since then under various other trademarks (see tradenames section), most notably Advil. ... This article is about the drug. ... Look up Pain in Wiktionary, the free dictionary. ... Purdue Pharma L.P., is privately-held pharmaceutical company founded by physicians. ... Coated 200 mg ibuprofen tablets Ibuprofen (INN) (IPA: ) (from the earlier and no longer correct nomenclature iso-butyl-propanoic-phenolic acid) is a non-steroidal anti-inflammatory drug (NSAID) originally marketed as Brufen, and since then under various other trademarks (see tradenames section), most notably Advil. ...


Oxycodone is a drug subject to abuse.[1][2] The drug is included in the sections for the most strongly controlled substances that have a commonly accepted medical use, including the German Betäubungsmittelgesetz III (narcotics law), the Swiss law of the same title, UK Misuse of Drugs Act (Class A), Canadian Controlled Drugs and Substances Act (CDSA), Dutch Opium Law (List 1), Austrian Suchtmittelgesetz (Addictives Act), and others. It is also subject to international treaties controlling psychoactive drugs subject to abuse or dependence. Misuse of Drugs Act is the name of several similar national drug control laws passed by countries in the Commonwealth of Nations and by the Republic of Ireland. ...


The abuse of OxyContin and its generic equivalents has greatly increased since the introduction of the sustained-release form of oxycodone. Illegal distribution of OxyContin occurs through pharmacy diversion, physicians, "doctor shopping," faked prescriptions, and robbery, all of which divert the pharmaceutical onto the illicit market. In Australia alone during 1999 and 2000, more than 260,000 prescriptions for narcotics and codeine-based medications were written to almost 9,000 known abusers at a cost of more than $750,000 AUD.[2] Purdue Pharma and its top executives pleaded guilty to felony charges that they misbranded and misled physicians and the public by claiming OxyContin was less likely to be abused, less addictive, and less likely to cause withdrawal symptoms.[3] The company also paid millions in fines relating to aggressive off-label marketing practices in several states.[4] The concept of doctor shopping relates to a patients addiction or reliance on a certain prescription drug or other medical treatment. ...

Contents

Chemistry

Oxycodone is commercially made from thebaine, an opiate alkaloid and minor component of opium.[5] The 14' hydroxy group increases potency by about 50% over hydrocodone.[citation needed] A minor constituent of opium, thebaine or paramorphine (C19H21NO3) is chemically similar to both morphine and codeine, but produces stimulatory rather than depressant effects. ... For other uses see Opiate (disambiguation), or for the class of drugs see Opioid. ... This article is about the drug. ... Hydrocodone or dihydrocodeinone is a semi-synthetic opioid derived from two of the naturally occurring opiates, codeine and thebaine. ...

Two 5mg oxycodone/APAP tablets.
Two 5mg oxycodone/APAP tablets.

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 hydrochloride 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] Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... Paracetamol (INN) (IPA: ) or acetaminophen (USAN), is the active metabolite of phenacetin, a so-called coal tar analgesic. ... Oxymorphone (Opana, Numorphan) or 14-Hydroxydihydromorphinone is a powerful semi-synthetic opioid analgesic that is derived from thebaine, and is approximately 6–8 times more potent than morphine. ... Codeinone is a strong Opiod. ...


Other oxycodone salts used around the world include the phosphate, sulfate, pectinate, tartrate, bitartrate, citrate and iodide.


Side effects

The most commonly reported effects include constipation, fatigue, dizziness, nausea, lightheadedness, headache, dry mouth, pruritus, and diaphoresis. Some patients have also experienced loss of appetite, nervousness, euphoria, anxiety, abdominal pain, diarrhea, dyspnea, and hiccups.[6] dyspnea, and hiccups, although these symptoms appear in less than 5% of patients taking oxycodone. Rarely, the drug can cause impotence, enlarged prostate gland, and decreased testosterone secretion.[5] Constipation or irregularity, is a condition of the digestive system where a person (or animal) experiences hard feces that are difficult to egest; it may be extremely painful, and in severe cases (fecal impaction) lead to symptoms of bowel obstruction. ... Many different terms are often used to describe what is collectively known as dizziness. ... For other uses, see Nausea (disambiguation). ... Light-headedness is a common and often unpleasant sensation of dizziness and/or feeling that one may be about to faint, which may be transient, recurrent, or occasionally chronic. ... A headache (cephalgia in medical terminology) is a condition of pain in the head; sometimes neck or upper back pain may also be interpreted as a headache. ... An itch (Latin: pruritus) is a sensation felt on an area of skin that makes a person or animal want to scratch it. ... Diaphoresis is excessive sweating commonly associated with shock and other medical emergency conditions. ... Look up euphoria, euphoric in Wiktionary, the free dictionary. ... This article is about state anxiety. ... In medicine, diarrhea, also spelled diarrhoea (see spelling differences), refers to frequent loose or liquid bowel movements. ... Dyspnea (R06. ... A hiccup is an involuntary spasm of the diaphragm. ... Dyspnea (R06. ... A hiccup is an involuntary spasm of the diaphragm. ... Impotence or, more clinically, erectile dysfunction is the inability to develop or maintain an erection of the penis for satisfactory sexual intercourse regardless of the capability of ejaculation. ... Male Anatomy The prostate is a gland that is part of male mammalian sex organs. ... Testosterone is a steroid hormone from the androgen group. ...


In high doses, overdoses, or in patients not tolerant to opiates, oxycodone can cause shallow breathing, bradycardia, cold, clammy skin, apnea, hypotension, pupil dilation, circulatory collapse, respiratory arrest, and death.[6] Bradycardia, as applied to adult medicine, is defined as a resting heart rate of under 60 beats per minute, though it is seldom symptomatic until the rate drops below 50 beat/min. ... Apnea, apnoea, or apnœa (Greek απνοια, from α-, privative, πνεειν, to breathe) is a technical term for suspension of external breathing. ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... Categories: Medicine stubs | Sign (medicine) ... Respiratory arrest is the cessation of the normal tidal flow of the lungs due to paralysis of the diaphragm, collapse of the lung or any number of respiratory failures. ...


Dosage and administration

Oxycodone can be administered orally, intranasally, via intravenous/intramuscular/subcutaneous injection, or rectally. The bioavailability of oral administration averages 60-87%, with rectal administration yielding the same results. Injecting oxycodone will result in a stronger effect and quicker onset. An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... Intramuscular injection is an injection of a substance directly into a muscle. ... The subcutis is the layer of tissue directly underlying the cutis. ... Suppository casting mould A suppository is a drug delivery system that is inserted either into the rectum (rectal suppository), vagina (vaginal suppository) or urethra (urethral suppository) where it dissolves. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ...

Oxycontin tablets of varying dosage.
Oxycontin tablets of varying dosage.

Percocet tablets, oxycodone with acetaminophen (paracetamol), 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. 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. Image File history File links Oxycont. ... Image File history File links Oxycont. ... Acetaminophen (USAN) or paracetamol (INN), is a popular analgesic and antipyretic drug that is used for the relief of fever, headaches, and other minor aches and pains. ... An opioid is a chemical substance that has a morphine-like action in the body. ... This article is about the drug. ...


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 vials 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.


Roxicodone is a generically made oxycodone product designed to have an immediate release effect for rapid pain relief, and is available in 5 (white), 15 (green), and 30 (light blue) mg tablets. Generic versions of Roxicodone may differ in color from the brand name tablets. The milligram (symbol mg) is an SI unit of mass. ...


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 (not all of these dosages are marketed in the US) and, due to its sustained-release mechanism, is effective for eight to twelve hours.[6] 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. Oxycontin is made of pure oxycodone hydrochloride. Nevertheless, an 80 mg Oxycontin has a mass of approximately 260 mg (not including the navy-colored coating) due to other compounds. The milligram (symbol mg) is an SI unit of mass. ... is the 291st day of the year (292nd in leap years) in the Gregorian calendar. ... Year 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ...


The controlled (sustained)-release preparations are essential to provide a background plasma level of analgesia in anyone with persistent pain. The immediate release preparations are useful for breakthrough pain, which can break through the controlled-release baseline medication. There are no trials to show that one manufacturer produces a more effective oxycodone product than any other.


History

Oxycodone is an opiate analgesic, and as such is a variation on an ancient theme beginning with the simple consumption or smoking of the alkaloid-bearing parts of Papaver somniferum, the opium poppy, first cultivated circa 3400 BC in lower Mesopotamia. Ancient Persians, Sumerians, Assyrians, Babylonians, and Egyptians found that smoking the extract derived from the seed pods yielded a pleasurable, peaceful feeling throughout the body. The Sumerians called the poppy plant "Hul Gil" or "joy plant". Cultivation and use spread quickly to the rest of the Persian Gulf, Levant and the Arabian Peninsula, eventually reaching India and China. Image File history File links Question_book-3. ... Binomial name L. The opium poppy, Papaver somniferum, is the type of poppy from which opium and all refined opiates such as morphine, thebaine, codeine, papaverine, and noscapine are extracted. ... Mesopotamia was a cradle of civilization geographically located between the Tigris and Euphrates rivers, largely corresponding to modern-day Iraq. ... For other uses of this term see: Persia (disambiguation) The Persian Empire is the name used to refer to a number of historic dynasties that have ruled the country of Persia (Iran). ... Sumeria may refer to: A back-formation from the adjective Sumerian, often used to mean the ancient civilisation more properly known as Sumer Sumeria, a disco artist best known for the 1978 hit Golden Tears 1970 Sumeria, an asteroid discovered in 1954 by Miguel Itzigsohn Donna Sumeria, a song on... For other uses, see Assyria (disambiguation). ... Babylonia was a state in southern Mesopotamia, in modern Iraq, combining the territories of Sumer and Akkad. ... Map of the Persian Gulf. ... The Levant The Levant (IPA: ) is an imprecise geographical term historically referring to a large area in the Middle East south of the Taurus Mountains, bounded by the Mediterranean Sea on the west, and by the northern Arabian Desert and Upper Mesopotamia to the east. ... Arabia redirects here. ...


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. To some extent this was achieved, as oxycodone does not "hit" the central nervous system with the same immediate punch as heroin or morphine and it does not last as long. The subjective experience of a "high" was still reported for oxycodone, however, and it made its way into medical usage in small increments in most Western countries until the introduction of high strength preparations with inert (inactive) binders radically boosted oxycodone use.[citation needed] Bayer AG (IPA pronunciation //) (ISIN: DE0005752000, NYSE: BAY, TYO: 4863 ) is a German chemical and pharmaceutical company founded in Barmen, Germany in 1863. ... For other uses, see Heroin (disambiguation). ...


The introduction of these higher strength preparations in 1995 resulted in increasing patterns of abuse.[1] Unlike Percocet, whose potential for abuse is somewhat limited by the presence of paracetamol (acetaminophen), OxyContin and other extended release preparations, contains only oxycodone and inert filler. Abusers simply crush the tablets, then either ingest the resulting powder orally, intranasally, via intravenous, intramuscular, or subcutaneous injection (by dissolving the powder), or rectally to achieve rapid absorption into the bloodstream. The tablets' coatings are removed, and they are crushed or chopped up by abusers to disable the time-release properties of the tablet, which allows the entire dose to "hit" the abuser at once. This rapid onset of the entire dose, or "hit", is referred to as "the rush" by drug abusers. This "rush" delivers a feeling of, what is described by abusers as, a "blissful apathy" and state of well-being, accompanied by a powerful and alluring euphoria. Injection of oxycodone directly into the bloodstream produces the most intense effects. Injection of OxyContin is also particularly dangerous since it contains binders which enable the time release of the drug. The vast majority of OxyContin-related deaths are attributed to ingesting substantial quantities of oxycodone in combination with another depressant of the central nervous system such as alcohol or benzodiazepines.[8] Paracetamol (INN) (IPA: ) or acetaminophen (USAN), is the active metabolite of phenacetin, a so-called coal tar analgesic. ... Acetaminophen (USAN) or paracetamol (INN), is a popular analgesic and antipyretic drug that is used for the relief of fever, headaches, and other minor aches and pains. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... Intramuscular injection is an injection of a substance directly into a muscle. ... The subcutis is the layer of tissue directly underlying the cutis. ... Grain alcohol redirects here. ... Benzodiazepine tablets The benzodiazepines are a class of drugs with hypnotic, anxiolytic, anticonvulsant, amnestic and muscle relaxant properties. ...


Oxycodone is becoming an increasingly publicized and known drug to the general public. However, it is also widely misunderstood, and many people lack factual knowledge about the drug. 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 in some areas.[2] 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.[9] The concept of doctor shopping relates to a patients addiction or reliance on a certain prescription drug or other medical treatment. ...


The increase of these illegal methods of obtainment coincides with the increase in the illegal use of this drug. The oxycodone contained in OxyContin produces typical opiate effects, and is, by some, considered a "reasonable substitute" for heroin, so much so that OxyContin is sometimes referred to as "hillbilly heroin". The most commonly diverted dosages are the 40mg and 80mg strengths.


Clinical use

In palliative care, oxycodone is viewed as a second line opioid to morphine, like hydromorphone and fentanyl. 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.[7] However, switching to an alternative opioid can be useful if adverse effects are troublesome, although the switch can be in either direction, ie. some patients have fewer adverse effects on switching from morphine to oxycodone (or hydromorphone or fentanyl), while others do better on switching to morphine. Palliative care (from Latin palliare, to cloak) is any form of medical care or treatment that concentrates on reducing the severity of disease symptoms, rather than providing a cure. ... This article is about the drug. ... Hydromorphone is a drug developed in Germany in the 1920s and introduced to the mass market beginning in 1926. ... Fentanyl is an opioid analgesic, first synthesized by Janssen Pharmaceutica (Belgium) in the late 1950s, with a potency many times that of morphine. ... An opioid is any agent that binds to opioid receptors found principally in the central nervous system and gastrointestinal tract. ...


Oxycodone has the disadvantage of accumulating in patients with renal and hepatic impairment. In addition, and unlike morphine and hydromorphone, it is metabolised by the cytochrome P450 enzyme system in the liver, making it vulnerable to drug interactions.[6] It is metabolised to the very active (but non-analgesic) oxymorphone,[10] and some people are fast metabolisers resulting in reduced analgesic effect but increased adverse effects, while others are slow metabolisers resulting in increased toxicity without improved analgesia.[11][12] These factors make the effects of oxycodone less predictable than opioids such as morphine or hydromorphone. Hydromorphone is a drug developed in Germany in the 1920s and introduced to the mass market beginning in 1926. ...


Manufacture and patents

Formulations containing oxycodone and other analgesics.
Formulations containing oxycodone and other analgesics.

An extended-release formulation of oxycodone, OxyContin, was first introduced to the US market by Purdue Pharma in 1996. It has multiple patents for their drug OxyContin, but has recently been involved in a series of ongoing legal battles deciding on whether or not these patents are valid. 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.[13] This decision allowed and led to the immediate announcement from Endo Pharmaceutical Holdings, Inc. that they would begin launching a generic version of all four strengths of OxyContin.[14] 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 currently Watson Pharmaceuticals is the exclusive U.S. distributor of the generic versions of OxyContin tablets. The agreement stipulates that "Purdue will manufacture and supply oxycodone HCI controlled-release tablets to Watson, which will market, sell, and distribute the authorized generic product in 10, 20, 40, and 80 milligram dosages in the United States".[15] Image File history File links Question_book-3. ... Image File history File links No higher resolution available. ... Purdue Pharma L.P., is privately-held pharmaceutical company founded by physicians. ... is the 158th day of the year (159th in leap years) in the Gregorian calendar. ... Year 2005 (MMV) was a common year starting on Saturday (link displays full calendar) of the Gregorian calendar. ... The United States Court of Appeals for the Federal Circuit, or simply the Federal Circuit, was founded in 1982 to combine similar federal cases to a specialized appellate court. ...


On February 1, 2006, the Federal Circuit Court of Appeals issued a revised decision that affirmed-in-part, vacated-in-part, and remanded-in-part their prior decision.[16] The court concluded, "The trial court's judgment that the patents-in-suit are unenforceable due to inequitable conduct is vacated, and the case is remanded for further proceedings consistent with this opinion. The trial court's judgment of infringement is affirmed." Purdue Pharma has since announced resolution of its infringement suits with Endo,[17] Teva,[18] and IMPAX.[19] Endo and Teva each agreed to cease selling generic forms of OxyContin, while IMPAX negotiated a temporary, and potentially renewable, license. is the 32nd day of the year in the Gregorian calendar. ... Year 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ...


Since the drug is a controlled substance, a prescription is required to obtain it, and is shown to be most frequently prescribed in the eastern United States. Purdue Pharma also exports OxyContin to wholesale distributors in Mexico and Canada. However, they have experienced increasing levels of illicit drug trafficking with the distribution outside of the U.S. that has led to certain responsive actions. The pill exported to Mexico is stamped with the letters "EX" instead of the customary "OC," and similarly the pills to Canada read "CDN" Purdue stopped exporting to Canada in 2001, and instead Canada imports the drug from a manufacturer in England. Despite these problems, OxyContin is one of the leading opioid painkillers on the market. In 2001, OxyContin was the highest sold drug of its kind, and in 2000, over 6.5 million prescriptions were written.[20]


Regulation

Regulation of oxycodone (and opioids in general) differs according to country, with different places focusing on different parts of the "supply chain".


In Australia, a General Practitioner can prescribe for short term treatment without consulting another practitioner or government body. Ongoing treatment requires approval from their state Health Department. Only twenty tablets are normally available per prescription on the Pharmaceutical Benefits Scheme, Australia's government-funded pharmaceutical insurance system, but a patient can potentially get up to sixty tablets for as little as $4.90AUD. Prescriptions for larger quantities require prior approval from Medicare Australia. These prescriptions (i.e. for chronic pain or cancer patients) require the prescriber to have referred the patient to another medical practitioner to confirm the need for ongoing treatment with narcotic analgesics. Pharmacists must record all incoming purchases of oxycodone products, and maintain a register of all prescription sales for inspection by their state Health Department on request. In addition details of all Pharmaceutical Benefits Scheme prescriptions for oxycodone are sent to Medicare Australia. This data allows Medicare Australia to assist prescribers to identify doctor-shoppers via a telephone hotline. The Pharmaceutical Benefits Scheme or PBS is a programme of the Australian Government that provides heavily subsidised prescription drugs to residents of Australia. ... Medicare Australia is an agency of the Australian Government that administers health-related programs including Medicare, the Pharmaceutical Benefits Scheme (PBS), and others. ...


In Canada, oxycodone is a controlled substance under Schedule I of the Controlled Drugs and Substances Act (CDSA). Every person who seeks or obtains the substance without disclosing authorization to obtain such substances 30 days prior to obtaining another prescription from a practitioner is guilty of an indictable offence and liable to imprisonment for a term not exceeding seven years. Possession for purpose of trafficking is guilty of an indictable offence and liable to imprisonment for life. The Controlled Drugs and Substances Act is Canadas federal drug control statute. ...


In the United States, regulation of prescription drugs comes from several different areas. The Food and Drug Administration (FDA) approves drugs for medical use, as well as sets regulations for the marketing of drugs, including controlled substances. The Drug Enforcement Administration (DEA) on the other hand, receives its regulatory authority from the Controlled Substances Act (CSA) [21 U.S.C. §§ 801-971], which "mandates that DEA prevent, detect and investigate the diversion of legally manufactured controlled substances while, at the same time, ensuring that there are adequate supplies to meet the legitimate medical needs in the United States".[21] Part of the regulation of prescription drugs is connected to their marketing and advertising. The FDA has authority over this sector under the Food, Drug, and Cosmetic (FD&C) Act and its implementing regulations. The Division of Drug Marketing, Advertising, and Communications (DDMAC) is "responsible for regulating prescription drug advertising and promotion," and has a "mission to protect the public health by ensuring that prescription drug information is truthful, balanced, and accurately communicated".[22] Simplified, Oxycodone is a schedule II controlled substance, which means to be filled there must be a written prescription which cannot have refills, nor can it be called in to a pharmacy by a physician. FDA redirects here. ... The DEAs enforcement activities may take agents anywhere from distant countries to suburban U.S. homes. ...


In Germany, only physicians (Ärzte) can prescribe Oxycodone which is sold by Mundipharma as Oxygesic. These physicians need to have a special BtM (Betäubungsmittel/English: Controlled Substance) number. Not all physicians have BtM numbers. BtM prescriptions are handled very cautiously and the central Federal Opium Bureau (Bundesopiumstelle) records all traffic. The BtM prescription has a different appearance from a regular prescription and includes three copies; one for the prescribing physician, one for the pharmacy and one for the BOP. Currently, 100 x 40mg Oxygesic tablets cost around €410. Oxygesic is sold as 10mg, 20mg, 40mg and 80mg tablets.


In Hong Kong, oxycodone is regulated under Schedule 1 of Hong Kong's Chapter 134 Dangerous Drugs Ordinance. It can only be used legally by health professionals and for university research purposes. The substance can be given by pharmacists under a prescription. Anyone who supplies the substance without a prescription can be fined $10,000(HKD). The penalty for trafficking or manufacturing the substance is a $5,000,000 (HKD) fine and/or life imprisonment. Possession of the substance for consumption without license from the Department of Health is illegal with a $1,000,000 (HKD) fine and/or 7 years of jail time. ISO 4217 Code HKD User(s) Hong Kong Inflation 2. ...


OxyContin misbranding and fraud

A bottle of 100 Oxycodone 10/325 will often sell at a vastly inflated price compared to its purchase cost.

Critics have accused Purdue of putting profits ahead of public interest by understating or ignoring the addictive potential of the drug.[23][24][25]


On May 10, 2007, Purdue Pharma and its top three executives pled guilty to felony charges that they purposely misbranded the painkiller OxyContin with intent to mislead and defraud. The company and the three executives, Michael Friedman, Howard Udell, and Paul D. Goldenheim, will pay a total of more than $634.5 million in fines and penalties. The group also pled guilty to a misdemeanor charge of misbranding OxyContin. Purdue Pharma and the three executives have admitted that Purdue Pharma fraudulently marketed OxyContin by falsely claiming that OxyContin was less addictive, less subject to abuse, and less likely to cause withdrawal symptoms than other pain medications when there was no medical research to support these claims and without FDA approval of these claims.[26] is the 130th day of the year (131st in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ...


Purdue Pharma also settled accusations regarding its promotion of OxyContin by paying $19.5 million to 26 states and the District of Columbia. The states complained that Purdue was encouraging physicians to prescribe the 12-hour time release drug for use every 8 hours, contrary to the dosage approved by the FDA.[4] ...


References

  1. ^ a b c Seidler, Raymond (July 2002). "Prescription Drug Abuse". Current Therapeutics. Retrieved on 2008-05-18. 
  2. ^ a b Staff writer. "Drugmaker to pay $19.5 mil to settle OxyContin lawsuit", Arizona Republic, Associated Press, 2007-05-09. Retrieved on 2008-05-18. 
  3. ^ a b Oxycodone Addiction. addictionsearch.com (2007-02-08). Retrieved on 2008-05-18.
  4. ^ a b c d Rappaport, Bob (2006-09-18). Package Insert: OxyContin (PDF). Food and Drug Administration. Retrieved on 2008-05-18.
  5. ^ a b (1999) Oxford Textbook of Palliative Medicine. Oxford: Oxford University Press. ISBN 0192625667. 
  6. ^ Summary of Medical Examiner Reports on Oxycodone-Related Deaths. DEA Office of Diversion Control. United States Department of Justice. Retrieved on 2008-05-18.
  7. ^ Beardsley PM, Aceto MD, Cook CD, Bowman ER, Newman JL, Harris LS (August 2004). "Discriminative stimulus, reinforcing, physical dependence, and antinociceptive effects of oxycodone in mice, rats, and rhesus monkeys". Exp Clin Psychopharmacol 12 (3): 163–72. doi:10.1037/1064-1297.12.3.163. PMID 15301633. Retrieved on 2008-05-18. 
  8. ^ Kalso, E. (May 2005). "Oxycodone". Journal of Pain & Symptom Management 29 (5): 47-56. 
  9. ^ Gasche Y, Daali Y, Fathi M, et al (December 2004). "Codeine intoxication associated with ultrarapid CYP2D6 metabolism". N. Engl. J. Med. 351 (27): 2827–31. doi:10.1056/NEJMoa041888. PMID 15625333. 
  10. ^ Otton SV, Wu D, Joffe RT, Cheung SW, Sellers EM (April 1993). "Inhibition by fluoxetine of cytochrome P450 2D6 activity". Clin. Pharmacol. Ther. 53 (4): 401–9. PMID 8477556. 
  11. ^ Purdue Pharma L.P. v. Endo Pharms. Inc, 410 F.3d 690 (Fed.Cir. 2005-06-07).
  12. ^ Purdue Pharma (2005-06-08). "Purdue Comments on Federal Court of Appeal Decision on OxyContin Patent Litigation". Press release. Retrieved on 2008-05-18.
  13. ^ Purdue Pharma (2005-10-28). "Purdue Appoints Watson Pharmaceuticals Exclusive Distributor of Authorized Generic Versions of OxyContin Tablets". Press release. Retrieved on 2008-05-18.
  14. ^ Purdue Pharma L.P. v. Endo Pharms. Inc., 438 F.3d 1123 (Fed.Cir. 2006-02-01).
  15. ^ Purdue Pharma (2006-08-28). "Purdue Pharma L.P. Announces Resolution of OxyContin® Patent Lawsuit with Endo Pharmaceuticals". Press release. Retrieved on 2008-05-18.
  16. ^ Purdue Pharma (2006-10-16). "Purdue Pharma L.P. Announces Signing of Consent Judgment Ending OxyContin® Tablets Patent Lawsuit with Teva Pharmaceuticals". Press release. Retrieved on 2008-05-18.
  17. ^ Purdue Pharma (2007-04-02). "Purdue Pharma L.P. Announces Agreement to End OxyContin® Patent Lawsuit with IMPAX Laboratories". Press release. Retrieved on 2008-05-18.
  18. ^ OxyContin. drugpolicy.org. Drug Policy Alliance. Retrieved on 2008-05-18.
  19. ^ OxyContin FAQs. DEA Office of Diversion Control. United States Department of Justice. Retrieved on 2008-05-18.
  20. ^ Jenkins, John K. (2002-02-12). OxyContin: Balancing Risks and Benefits. Statement Before U.S. Senate Committee on Health, Education, Labor, and Pensions. Food and Drug Administration. Retrieved on 2008-05-18.
  21. ^ Bauerlein, Valerie. "Popular Painkiller Mired in Controversy" (reprint), The State, 2001-09-23. Retrieved on 2008-05-18. 
  22. ^ Rosenberg, Debra. "Drugs: Profits vs. Pain Relief" (reprint), Newsweek, 2001-07-02. Retrieved on 2008-05-18. 
  23. ^ "Editorial: Selling Drugs Legally, But Not Always Safely" (reprint), Roanoke Times, 2001-06-13. Retrieved on 2008-05-18. 
  24. ^ Chasan, Emily. "Purdue Frederick Pleads Guilty in OxyContin Case", Reuters, 2007-05-10. Retrieved on 2008-05-18. 

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The Associated Press, or AP, is an American news agency, the worlds largest such organization. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ... is the 129th day of the year (130th in leap years) in the Gregorian calendar. ... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Anno Domini (or common era), in accordance to the Gregorian calendar. ... is the 138th day of the year (139th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) was a common year starting on Monday of the Gregorian calendar in the 21st century. ... is the 39th day of the year in the Gregorian calendar. ... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Anno Domini (or common era), in accordance to the Gregorian calendar. ... is the 138th day of the year (139th in leap years) in the Gregorian calendar. ... 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For animal rights group, see Justice Department (JD) The United States Department of Justice (DOJ) is a Cabinet department in the United States government designed to enforce the law and defend the interests of the United States according to the... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Anno Domini (or common era), in accordance to the Gregorian calendar. ... is the 138th day of the year (139th in leap years) in the Gregorian calendar. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Anno Domini (or common era), in accordance to the Gregorian calendar. ... is the 138th day of the year (139th in leap years) in the Gregorian calendar. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ... Purdue Pharma L.P., is privately-held pharmaceutical company founded by physicians. ... Year 2005 (MMV) was a common year starting on Saturday (link displays full calendar) of the Gregorian calendar. ... is the 159th day of the year (160th in leap years) in the Gregorian calendar. ... For information on Wikipedia press releases, see Wikipedia:Press releases. ... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Anno Domini (or common era), in accordance to the Gregorian calendar. ... is the 138th day of the year (139th in leap years) in the Gregorian calendar. ... Purdue Pharma L.P., is privately-held pharmaceutical company founded by physicians. ... Year 2005 (MMV) was a common year starting on Saturday (link displays full calendar) of the Gregorian calendar. ... is the 301st day of the year (302nd in leap years) in the Gregorian calendar. ... For information on Wikipedia press releases, see Wikipedia:Press releases. ... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Anno Domini (or common era), in accordance to the Gregorian calendar. ... is the 138th day of the year (139th in leap years) in the Gregorian calendar. ... Purdue Pharma L.P., is privately-held pharmaceutical company founded by physicians. ... Year 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ... is the 240th day of the year (241st in leap years) in the Gregorian calendar. ... For information on Wikipedia press releases, see Wikipedia:Press releases. ... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Anno Domini (or common era), in accordance to the Gregorian calendar. ... is the 138th day of the year (139th in leap years) in the Gregorian calendar. ... Purdue Pharma L.P., is privately-held pharmaceutical company founded by physicians. ... Year 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ... is the 289th day of the year (290th in leap years) in the Gregorian calendar. ... For information on Wikipedia press releases, see Wikipedia:Press releases. ... 2008 (MMVIII) is the current year, a leap year that started on Tuesday of the Anno Domini (or common era), in accordance to the Gregorian calendar. ... is the 138th day of the year (139th in leap years) in the Gregorian calendar. ... Purdue Pharma L.P., is privately-held pharmaceutical company founded by physicians. ... 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Clonidine is a direct-acting adrenergic agonist prescribed historically as an anti-hypertensive agent. ... Cyclobenzaprine is a skeletal muscle relaxant and a central nervous system (CNS) depressant. ... Duloxetine (brand names Cymbalta, Yentreve, and in parts of Europe, Xeristar or Ariclaim) is a drug which primarily targets major depressive disorder (MDD), generalized anxiety disorder (GAD), pain related to diabetic peripheral neuropathy and in some countries stress urinary incontinence (SUI). ... Gabapentin (brand name Neurontin) is a medication originally developed for the treatment of epilepsy. ... Categories: Possible copyright violations ... Orphenadrine (Norflex®, Disipal®, Banflex®, Flexon® and others) is an anticholinergic and NMDA receptor antagonist [1]drug belonging to the ethanolamine class of antihistamines. ... Trazodone (Desyrel®, Trittico®, Thombran®, Trialodine®) is a psychoactive compound with sedative, anxiolytic, and antidepressant properties. ... Ziconotide is a non-opioid, non local anesthetic used for the amelioration of chronic pain. ...

  Results from FactBites:
 
OXYCODONE (Trade Names: Tylox®, Percodan®, OxyContin®) (776 words)
Oxycodone controlled-release tablets are prescribed for the management of moderate to severe pain when a continuous, around-the-clock analgesic is needed for an extended period of time.
Oxycodone, [4,5-epoxy-14-hydroxy-3-methoxy-17-methyl-morphinan-6-one, dihydrohydroxycodeinone] is a semi-synthetic opioid agonist derived from thebaine, a constituent of opium.
A 10 mg dose of orally-administered oxycodone is equivalent to a 10 mg dose of subcutaneously administered morphine as an analgesic in the normal population.
Oxycodone Drug Addiction Information & Treatment (2294 words)
Oxycodone controlled-release tablets are prescribed for the management of moderate to severe pain when a continuous, around-the-clock analgesic is needed for an extended period of time.
Oxycodone is a semi-synthetic opioid agonist derived from thebaine, a constituent of opium.
A 10 mg dose of orally-administered oxycodone is equivalent to a 10 mg dose of subcutaneously administered morphine as an analgesic in the normal population.
  More results at FactBites »

 
 

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