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Oxycodone is a semi-synthetic opioid, synthesized from tebaine, an opioid alkaloid contained in a Persian poppy and one of the many alkaloids contained in an opium poppy. It is a moderately strong opioid analgesic and is usually prescribed to relieve moderate to severe pain. Oxycodone was developed in 1917 in Germany as one of several semisynthetic opioids in an attempt to create a compound that exceeds existing opioids in some ways.

Systematic (IUPAC) name: (5R, 9R, 13S, 14S) -4,5α-epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
    Trade names: Roxicodone, OxyContin, Oxecta, OxyIR, Endone, Oxynorm, OxyNEO
    Category of the drug during pregnancy:
    Australia: C
    USA: B (no risk in animal studies)
    The risk of addiction: high
    Methods of administration: oral, intramuscular, intravenous, intranasal, subcutaneous, transdermal, rectal, epidural [1]
    Legal status
    Australia: S8 (controlled substance)
    Canada: List I
    Denmark: Anlage III (prescription only)
    UK: Class A
    USA: List II
    ℞ (prescription only)
    Bioavailability: 60-87% [2]
    Protein binding: 45% [2]
    Metabolism: liver, first of all, CYP3A and, to a lesser extent, CYP2D6 to oxymorphone Biological half-life: 2-4 hours.
    Excretion: urine (83%)
    Synonyms: dihydrohydroxycodeinone, 14-hydroxydihydrocodeinone, 6-deoxy-7,8-dihydro-14-hydroxy-3-O-methyl-6-oxomorphine [3]
    Formula: C18H21NO4
    Molar mass: 315.364 g / mol
    Solubility in HCl water: 166 mg / ml (20 ° C)

Oxycodone is available as a single-ingredient drug in immediate release and controlled release forms. In the UK, parenteral formulas of 10 mg / ml and 50 mg / ml are available for intravenous / intramuscular administration. Also available are combined formulas in the form of immediate-release drugs, with non-narcotic ingredients, such as nonsteroidal anti-inflammatory drugs (NSAIDs) and paracetamol (acetaminophen); The combination with naloxone is available in controlled release tablets. In the case of injection, naloxone removes the symptoms of opioid withdrawal and blocks the effect of the drug.


Medical use

Oxycodone has been used in clinical practice since 1916 to control acute or chronic pain from moderate to moderately severe. It has been found that this drug improves the quality of life in people with many types of pain. Experts are divided regarding its use in non-cancer-related chronic pain, since most opioids have a great potential for developing addiction and can also create paradoxical pain sensitivity. Oxycodone is available as a controlled-release tablet designed to be taken every 12 hours. A 2006 review found that controlled-release oxycodone is comparable to instant-release oxycodone, morphine and hydromorphone, in the management of moderate to severe cancer pain, with fewer side effects than morphine. The author concluded that controlled release oxycodone is an alternative to morphine and first-line drugs for cancer pain. In 2014, the European Palliative Care Association recommended oral oxycodone as an alternative to second-line oral morphine for the treatment of cancer pain. In the US, sustained-release oxycodone is approved for use in children under 11 years of age. Approved indications for use include pain relief for cancer, trauma, or pain due to major surgery in children who have already received opioids that can tolerate a dose of at least 20 mg of oxycodone per day; this is an alternative to Duragesic (fentanyl), the only other post-release opioid analgesic approved for use in children.



In the United States, oxycodone is approved for oral use only, is available as tablets and oral solutions. In the United Kingdom, oxycodone is also approved for intravenous (IV) and intramuscular (VM) use. During the First World War, when oxycodone was first used in Germany, it was widely used by explosives and VMs for the treatment of postoperative pain in Union State soldiers.

Oxycodone appears to have a significant antidepressant effect.


Side effects

The main side effects of oxycodone include euphoria, constipation, fatigue, dizziness, nausea, vomiting, dry mouth, anxiety, itching and sweating. 6) Less common side effects (observed in less than 5% of patients) include loss of appetite, nervousness, abdominal pain, diarrhea, urinary retention, shortness of breath and hiccups. When taken in high doses, overdose, or in some people who are not tolerant of opioids, oxycodone can cause shallow breathing, bradycardia, cooling and moisturizing of the skin, shortness of breath, hypotension, miosis, heart failure, respiratory arrest, and death. In order to reduce side effects, a combination of oxycodone with naloxone in controlled-release tablets was developed.


Addiction, addiction and withdrawal syndrome

The main side effects of oxycodone include euphoria, constipation, fatigue, dizziness, nausea, vomiting, dry mouth, anxiety, itching and sweating. Less common side effects (observed in less than 5% of patients) include loss of appetite, nervousness, abdominal pain, diarrhea, urinary retention, shortness of breath and hiccups. When taken in high doses, overdose, or in some people who are not tolerant of opioids, oxycodone can cause shallow breathing, bradycardia, cooling and moisturizing of the skin, shortness of breath, hypotension, miosis, heart failure, respiratory arrest, and death. In order to reduce side effects, a combination of oxycodone with naloxone in controlled-release tablets was developed.

Addiction, addiction and withdrawal syndrome

The risk of severe withdrawal symptoms increases if the patient becomes physically dependent on the drug and suddenly stops taking it. According to the rules of medicine, if the drug was taken regularly for a long period of time, it should be stopped gradually, not abruptly. People who regularly use oxycodone recreationally or at doses higher than prescribed have an even higher risk of severe withdrawal symptoms. Symptoms of withdrawal of oxycodone, like other opiates, may include “anxiety, panic attacks, nausea, insomnia, muscle aches, muscle weakness, fever, and other flu-like symptoms.” Withdrawal symptoms were also reported in newborns whose mothers took oxycodone during pregnancy, either orally or injecting. eight)
Hormonal imbalance

As with other opiates, the chronic use of oxycodone (particularly in higher doses) often causes hypogonadism or hormonal imbalance at the same time.

Detection in biological fluids

Oxycodone and / or its major metabolites can be detected in the blood or urine, in order to track their elimination from the body, the possibility of abuse, to confirm the diagnosis of poisoning or help forensic examination in the investigation of death. Many commercial opiate screening tests cross-react with oxycodone and its metabolites, but chromatographic methods can easily distinguish oxycodone from other opiates.

Mechanism of action

In 1997, a group of Australian researchers suggested (based on a study in rats) that oxycodone acts on kappa-opioid receptors, unlike morphine, which acts on mu-opioid receptors. Further studies by this group of scientists have shown that the drug appears to be a κ2b opioid agonist. However, this conclusion was challenged primarily on the basis that oxycodone produces effects characteristic of μ-opioid agonists, mainly because oxycodone is metabolized in the liver to oxymorphone as a metabolite, which is more powerful an opioid agonist with a stronger / higher binding affinity for the mu-opioid receptors compared to oxycodone. A study conducted in 2006 by a group of Japanese scientists showed that, presumably, the effect of oxycodone is mediated by different receptors in different situations. In particular, in diabetic mice, the κ-opioid receptors appear to be involved in the antinociceptive effects of oxycodone, while in non-diabetic mice, these effects appear to be primarily responsible for the μ1-opioid receptors. After oxycodone binds to opioid receptors, the G-protein complex is released, which inhibits the release of neurotransmitters by the cell by reducing the amount of cAMP produced, closing Ca ++ channels and opening K channels.


After taking a dose of normal oral oxycodone, peak plasma levels of the drug are reached in about one hour; in contrast, after taking a dose of oxycontin (a controlled release oral preparation), peak plasma levels of oxycodone are observed after about 3 hours.


Oxycodone in the blood is distributed in skeletal muscle, liver, gastrointestinal tract, lungs, spleen and brain. Conventional oral medications begin to reduce pain within 10–15 minutes when taken on an empty stomach; OxyContin begins to reduce pain within one hour.


Oxycodone is metabolized to a and β oxycodol; Oxymorphone, and then in α and β Oxymorphol and noroxymorphone; and noroxycodone, then α and β noroxycodol and noroxymorphone (N-desmethyloxycodone). (14-methoxymetopone, which, in turn, becomes 14-hydroxydihydromorphone). These metabolites act only in the human body. The rabbits were found six metabolites oxycodone (14 gidroksidigidromorfinon, 14 gilroksidigidrokodein, 14 gidroksidigidrokodeinon N-oxide {oxycodone N-oxide}, 14 gidroksidigidroizokodein, 14 gidroksidigidrokodeine N-oxide and noroksikodon), some of which are believed to are to some extent active metabolites, although research using traditional oral oxycodone has shown that only oxycodone, and not its metabolites, is primarily responsible for the opioid effects of the drug on the brain. Oxycodone is metabolized by the cytochrome P450 enzyme system in the liver, which makes it vulnerable to interactions with other drugs. Some people have a fast metabolism, which leads to a decrease in the analgesic effect, but an increase in adverse effects, while other people have a slower metabolism, which leads to an increase in toxicity without increasing analgesia. The dose of oxycontin should be reduced in patients with reduced liver function.
Excretion from the body

Oxycodone and its metabolites are mainly excreted in the urine and sweat; thus, it accumulates in patients with impaired renal function.

Dosage and administration

Oxycodone can be administered orally, intranasally, intravenously, intramuscularly or subcutaneously, or rectally. The oral bioavailability of oxycodone on average is 60-87%, with rectal administration the same results are observed; with intranasal administration, bioavailability varies in individuals with an average of 46%.

Morphine equivalent

When administered orally, 20 mg of immediate release oxycodone is equivalent to 30 mg of morphine. Oxycodone sustained release is two times more potent than oral morphine.


The chemical name oxycodone is derived from codeine. The chemical structures of these substances are very similar, differing only in the fact that oxycodone has a hydroxyl group on carbon-14 (codeine has only hydrogen at this place). Oxycodone has its 7,8-dihydro function. Codeine has a double bond between the two carbon atoms; and oxycodone has a carbonyl group (as in ketones) instead of a hydroxyl group in codeine. Oxycodone is also similar to hydrocodone, differing only in the fact that it has a hydroxyl group on carbon-14. Extended names for oxycodone in the scientific literature include “dihydrohydroxycodeinone”, “Eucodal”, “Eukodal”, “14-hydroxydihydrocodeinone” and “Nucodan”. In the UNESCO convention, translations of the word “oxycodone” are oxycodon (Dutch), oxycodone (French), oxicodona (Spanish), الأوكسيكودون (Arabic), 羟 考 酮 (Chinese) and oxycodone (Russian). “Oxycodone” should not be confused with “oxandrolone”, “oxazepam”, “oxybutinin”, “oxytocin” or “Roxanol”. From the point of view of biosynthesis, oxycodone is naturally found in the nectar extracts of the plant from the family of orchids; together with other opioids: 3- {2- {3- {3-benzyloxypropyl} -3-indole and 7,8-didehydro 4,5-epoxy-3,6-D-morphinan. Oxycodone is sold in the form of various salts, most often in the form of the hydrochloride salt. The conversion rate of the free base of various salts: hydrochloride (0.896), bitartrate (0.667), tartrate (0.750), samfosulfonat (0.576), pectinate (0.588), phenylpropionate (0.678), sulfate, (0.887), phosphate (0.763) and polyethylene terephthalate ( 0.792). Hydrochloride is the basis of most American oxycodone products, while bitartrate, tartrate, pectinate, terephthalate, and phosphate salts are also available in European products. Iodomethane and hydroiodide are mentioned in old European editions.


Freund and Speyer from the University of Frankfurt in Germany first synthesized oxycodone from thebaine in 1916, several years after the German pharmaceutical company Bayer stopped mass production of heroin because of the dangers associated with its use and the development of addiction. It was hoped that the drug from tebaine would have an analgesic effect, by analogy with morphine and heroin, but would be less addictive. To some extent, this has been achieved, since oxycodone does not have the same immediate effect as heroin or morphine, and does not act so long. The first clinical use of the drug was recorded in 1917, a year after it was first developed. It was first marketed in the United States in May 1939. In early 1928, Merck introduced a combination preparation containing scopolamine, oxycodone and ephedrine, called SEE, denoting the first letters of the ingredients in German, which was later renamed Scophedal (SCOPolamine, EFEDRIN and YUKODAL). This combination is essentially an analogue of oxycodone from the Twilight Sleep morphine-based preparation, with the addition of ephedrine to reduce the effects on the circulatory and respiratory systems. In the personal notes of Adolf Hitler’s doctor, Dr. Theodore Morell, it says that Hitler was injected with Eukodal (oxycodone). In the early 1960s, the United States government classified oxycodone as a drug from Schedule II. In 1995, the FDA approved OxyContin, a sustained-release oxycodone form.


The International Narcotics Control Board estimated that in 1998, 11.5 short tons (23,000 pounds) of oxycodone were produced worldwide. 18) By 2007, this figure had risen to 75.2 tons (150,400 pounds). The United States accounted for 82% of oxycodone consumption in 2007 (51.6 tons). Canada, Germany, Australia and France combined accounted for 13% of oxycodone consumption in 2007. In 2010, 1.3 tons of oxycodone was illegally manufactured. This accounted for 0.8% of consumption. These illegal pills were subsequently withdrawn by the US Drug Enforcement Administration, according to the International Narcotics Control Board. The Council also reported production of 122.5 tons in 2010. This number has decreased from a record 135.9 tons in 2009.


Legal status

Oxycodone is governed by the international drug conventions. In addition, the regulation of oxycodone is subject to national laws, which differ in different countries. The 1931 Convention on the Limitation of the Production and Regulation of the Distribution of Narcotic Drugs of the League of Nations included oxycodone. The United Nations Single Convention on Narcotic Drugs, which replaced the 1931 agreement, categorized oxycodone in Schedule I. The global drug restrictions from Schedule I include “restrictions solely on the medical and scientific goals of production, export, import, distribution, trade, use and storage” these drugs; “Requirements of a prescription from a doctor for the sale of [these] drugs to individuals”; and “preventing the accumulation of” these drugs “above the norm necessary.


Oxycodone is included in Appendix I (of the Single Convention on Narcotic Drugs) of the Commonwealth Narcotic Drugs Act 1967. It is also included in Appendix 8 of the Australian Standard for Universal Drug and Poison Planning (“Poison Standard”), which means that it is a “controlled drug … that must be available for use, but requires a restriction of production, supply, distribution, ownership and use to reduce abuse, misuse and physical or physical ihologicheskuyu dependence. “


Oxycodone is a regulated substance in accordance with Schedule I of the Law on Controlled and Psychotropic Substances.
Canada – Legislative Changes

In February 2012, a law was passed in Ontario to expand the existing drug tracking system for publicly funded drugs, including privately insured. This database will function in order to detect and track a patient’s attempts to get a prescription from several doctors or from several pharmacies. Similar legislation has been proposed in other provinces, and some, such as Nova Scotia, already have legislation in place to monitor the use of prescription drugs. These changes coincided with other changes in Ontario legislation aimed at controlling the abuse of painkillers and highly addictive substances, such as oxycodone. As of February 29, 2012, a law was passed in Ontario by which oxycodone was excluded from the list of drugs for public use. This was the first case of drug exclusion due to its addictive properties. The new law prohibits the discharge of OxyNeo, with the exception of some patients under the exclusive access program, including palliative care, as well as in other extenuating circumstances. Patients who have already been prescribed oxycodone will receive coverage for another year for OxyNeo, and after that, the drug will be banned if the patient is not in the exclusive access program. A significant amount of legislative activity arises from the decision of Purdue Pharma in 2011 to begin modifying the formula Oxycontin, to make it more difficult to crush or inject. The new formula OxyNeo is designed to prevent such use and retains its effectiveness as a painkiller. With the introduction of the Drug Safety and Awareness Act, Ontario seeks to focus on addiction, especially in monitoring and identifying problems with prescription opioids, as well as on education of patients, doctors and pharmacists. This law, introduced in 2010, is committed to creating a single database to fulfill this intent. Both the public and the medical community reacted positively to the legislation, although concerns were expressed regarding the effects of legislative changes. Since laws are largely governed by the provinces, many say that a national strategy is needed to prevent smuggling across provincial borders. As of 2015, since 2012, Purdue Pharma’s OxyNEO, a drug resistant to abuse, has been approved throughout Canada and six generic versions of oxycontin for prescription sales. In June 2015, then-Federal Health Minister Rona Ambrose announced that within three years all oxycodone products sold in Canada should be protected from unauthorized access. Some experts warn that generic manufacturers cannot have technological capabilities for this purpose, perhaps giving Purdue Pharma a monopoly on the market for this opiate.

Canada: litigation

Across Canada, several lawsuits were filed against the Purdue group of companies and their affiliates. The plaintiffs argue that pharmaceutical manufacturers do not comply with quality standards. These claims refer to earlier court decisions in the United States that decree Purdue is responsible for unlawful marketing and trademark marking practices. Since 2007, Purdue has paid more than € 650 million in resolving disputes or paying criminal fines.


The drug is included in Appendix III of the Anti-Drug Act (Betäubungsmittelgesetz or BtMG). The law only allows doctors, dentists, and veterinarians (Ärzte, Zahnärzte und Tierärzte) and the federal government to regulate prescriptions (for example, requiring reporting).

Hong Kong

Oxycodone is regulated in accordance with Part I of Annex 1, Chapter 134, on the Dangerous Drugs Ordinance in Hong Kong.


Oxycodone is a prohibited substance in Japan. Its import and export is strictly limited to specially authorized organizations that have prior authorization to import it. One of the leaders of Toyota, who claimed he did not know about the law, was arrested for importing oxycodone to Japan.


Oxycodone is listed as a drug class of the Singapore Anti-Drug Abuse Act, which means that crimes related to this drug mean the most serious level of punishment. The conviction for the unauthorized manufacture of the drug is associated with a minimum punishment of 10 years in prison and corporal punishment of 5 blows with a cane, and the maximum penalty of life imprisonment or 30 years in prison and 15 blows with a cane. The minimum and maximum fines for unauthorized drug trafficking, respectively, entail 5 years ’imprisonment and 5 strikes with a cane and 20 years imprisonment and 15 strikes with a cane.

Great Britain

Oxycodone is a Class A Drug Abuse Act. For class A drugs that are “considered to be the most capable of causing harm,” non-prescription is punishable up to seven years in prison, an unlimited fine or two penalties at once. Illegal sale of the drug is punishable up to life imprisonment, an unlimited fine, or two penalties at once. In addition, oxycodone is listed on Drugs, according to the 2001 Drug Abuse Regulations, which “provides for certain exceptions to the provisions of the Anti-Drug Abuse Act of 1971”.


According to the Controlled Substances Act, adopted in 1971 by President Richard Nixon, oxycodone is a controlled substance from Schedule II, either alone or as part of a multi-component drug. The DEA number for oxycodone, both for sale and for use in the production of other opioids – ACSCN 9143. In 2013, the following annual total production quotas were approved: 131.5 metric tons for sale, compared with 153.75 in 2012 and 10.25 metric tons for the production of other opioids, unchanged from last year.




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