What is oxycodone and what is its primary medical use?

Oxycodone is a semi-synthetic opioid medication primarily used to treat moderate to severe acute or chronic pain when other treatments are insufficient. It is available under brand names like Roxicodone and OxyContin.

What are some of the common brand names associated with oxycodone?

Oxycodone is sold under various brand names, including Roxicodone for immediate-release formulations and OxyContin for its extended-release form. Other brand names mentioned include Longtec and Shortec.

What is the addictive potential and abuse liability of oxycodone?

Oxycodone is known to be highly addictive and is frequently abused as a drug. Its high potential for dependence and substance abuse is a significant concern.

How is oxycodone typically administered, and what are its available formulations?

Oxycodone is usually taken orally and is available in both immediate-release and controlled-release formulations. In some regions, like the UK, it can also be administered via injection. Other routes of administration include sublingual, intramuscular, intravenous, intranasal, subcutaneous, transdermal, rectal, and epidural.

What is the typical onset and duration of pain relief for immediate-release oxycodone?

For the immediate-release formulation, pain relief typically begins within 10 to 30 minutes and lasts for up to six hours. Peak plasma levels are usually reached within 30 to 60 minutes.

What other medications are commonly combined with oxycodone in prescription products?

Oxycodone is available in combination products with other medications such as paracetamol (acetaminophen), ibuprofen, naloxone, naltrexone, and aspirin. These combinations can offer synergistic effects or mitigate side effects.

What are some common side effects associated with oxycodone use?

Common side effects include euphoria, constipation, nausea, vomiting, loss of appetite, drowsiness, dizziness, itching, dry mouth, and sweating. These effects are typical of opioid medications.

Beyond common side effects, what are some less common but potentially serious side effects of oxycodone?

Less common side effects can include addiction, dependence, substance abuse, irritability, depression, mania, delirium, hallucinations, hypoventilation, gastroparesis, bradycardia, and hypotension. These indicate more significant physiological or psychological impacts.

What is the risk of opioid withdrawal if oxycodone is stopped abruptly?

There is a high risk of experiencing severe withdrawal symptoms if a patient who has become physically dependent on oxycodone discontinues the medication abruptly. Gradual tapering is the medically recommended approach for withdrawal to mitigate these symptoms.

What are the symptoms of oxycodone withdrawal?

Symptoms of oxycodone withdrawal can include anxiety, panic attacks, nausea, insomnia, muscle pain, muscle weakness, fevers, and flu-like symptoms, similar to withdrawal from other opioids.

Can oxycodone use during pregnancy be considered safe?

The source indicates that oxycodone use in early pregnancy appears relatively safe. However, it is always crucial to consult a healthcare provider regarding medication use during pregnancy.

What happens to hormone levels with chronic oxycodone use?

Chronic use of oxycodone, particularly at higher doses, can lead to hypogonadism, which is a reduction in sex hormone levels. The specific impact on testosterone levels is noted as unknown.

What are the symptoms of an oxycodone overdose?

An overdose of oxycodone can cause shallow breathing, slowed heart rate, cold and clammy skin, pauses in breathing, low blood pressure, constricted pupils, circulatory collapse, respiratory arrest, and potentially death. These are serious signs requiring immediate medical attention.

How does oxycodone's analgesic effect compare to morphine?

When taken orally, oxycodone is approximately 1.5 times more potent in its analgesic effect compared to an equivalent amount of morphine. This means a lower dose of oxycodone may provide similar pain relief.

When and where was oxycodone first synthesized?

Oxycodone was first synthesized from thebaine in Germany in 1916 by Martin Freund and Edmund Speyer.

When was oxycodone first used medically?

The first documented medical use of oxycodone occurred in Germany in 1917, one year after its synthesis.

What is the mechanism of action for oxycodone?

Oxycodone acts by activating the mu-opioid receptor (MOR), which is the primary biological target responsible for its pain-relieving effects. This receptor activation modulates pain signaling pathways.

How is oxycodone metabolized in the body?

Oxycodone is metabolized in the liver primarily by the enzymes CYP3A4 and, to a lesser extent, CYP2D6. This complex metabolic process results in several metabolites, some of which are also pharmacologically active.

What are the main metabolites of oxycodone?

The primary metabolites of oxycodone are noroxycodone (accounting for about 70% of a dose), noroxymorphone, and oxymorphone. These are formed through N-demethylation and O-demethylation processes.

What is the bioavailability of oral oxycodone?

The bioavailability of oral oxycodone ranges from 60% to 87%. This indicates that a substantial portion of the ingested dose is absorbed and becomes available in the bloodstream.

What is the elimination half-life of immediate-release and controlled-release oxycodone?

The elimination half-life for immediate-release oxycodone is typically 2-3 hours, while the controlled-release formulation has a slightly longer half-life of about 4.5 hours. This difference influences dosing frequency.

What is the duration of action for immediate-release and controlled-release oxycodone?

Immediate-release oxycodone provides pain relief for 3-6 hours, whereas controlled-release formulations like OxyContin are designed to last for 10-12 hours, allowing for less frequent dosing.

What is the chemical name for oxycodone?

The IUPAC name for oxycodone is (5R,9R,13S,14S)-4,5α-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one.

What is the chemical formula and molar mass of oxycodone?

The chemical formula for oxycodone is C18H21NO4, and its molar mass is approximately 315.369 g/mol.

How does oxycodone's interaction with the mu-opioid receptor (MOR) affect neurotransmitter release?

When oxycodone binds to the MOR, it triggers intracellular signaling that inhibits neurotransmitter release by reducing cyclic AMP (cAMP) production, closing calcium channels, and opening potassium channels. This mechanism underlies its pain-relieving effects.

What is the significance of CYP3A4 and CYP2D6 in oxycodone metabolism?

CYP3A4 and CYP2D6 are crucial liver enzymes responsible for metabolizing oxycodone. Inhibitors or inducers of these enzymes can significantly alter oxycodone's plasma concentrations and its therapeutic or toxic effects.

How does genetic variation in CYP enzymes affect oxycodone's efficacy and toxicity?

Genetic polymorphisms in CYP2D6 and CYP3A4 can lead to variations in how individuals metabolize oxycodone, influencing its analgesic effects and the risk of toxicity. This contributes to the wide differences observed in patient responses.

What is the role of noroxycodone and oxymorphone as active metabolites of oxycodone?

Noroxycodone and oxymorphone are active metabolites of oxycodone that also bind to mu-opioid receptors. Oxymorphone, in particular, has a higher affinity for the MOR than oxycodone itself and contributes significantly to the overall analgesic effect.

What are the legal classifications of oxycodone in different countries?

Oxycodone is classified as a Schedule II controlled substance in the United States, Class A in the UK, and Schedule I under the UN Single Convention on Narcotic Drugs. It holds various controlled substance classifications in other nations, reflecting its potential for abuse.

What was the historical significance of the drug Skophedal (containing oxycodone)?

Skophedal, a combination product including oxycodone, was developed in Germany and used by the Wehrmacht as a battlefield analgesic. It was noted for providing deep analgesia, euphoria, and tranquilization, and was reportedly favored over other opiates for its reduced sedation at equianalgesic doses.

How did Purdue Pharma's development of OxyContin impact the use and perception of oxycodone?

Purdue Pharma developed OxyContin, an extended-release formulation, which was approved in 1995. Marketed as a breakthrough pain reliever, it became widely used but also significantly contributed to the opioid epidemic due to its high potential for abuse and addiction.

What are the concerns regarding the 12-hour dosing schedule of OxyContin?

Concerns exist that the 12-hour dosing schedule for OxyContin may wear off prematurely for many patients, leading to withdrawal symptoms and potentially fostering addiction. Critics argue this schedule was promoted by Purdue Pharma despite evidence of its inadequacy for some individuals.

What is the relationship between oxycodone and the opioid epidemic in the United States?

Oxycodone, particularly through the widespread use and abuse of OxyContin, has been a significant factor in the opioid epidemic in the United States. It has been linked to a substantial number of overdose deaths and widespread addiction issues.

How has the reformulation of OxyContin attempted to address abuse?

Purdue Pharma reformulated OxyContin using a polymer to make the pills more difficult to crush or dissolve, aiming to reduce non-medical use and abuse. The FDA subsequently approved labeling for this reformulated version as abuse-resistant.

What is the chemical structure difference between oxycodone and codeine?

Oxycodone differs from codeine chemically by having a hydroxy group at carbon-14, a 7,8-dihydro feature instead of a double bond, and a carbonyl group replacing codeine's hydroxyl group at position 6. These structural modifications affect its properties.

Can oxycodone be detected in biological fluids?

Yes, oxycodone and its metabolites can be measured in biological fluids like blood or urine. This testing is used for monitoring drug clearance, detecting non-medical use, confirming poisoning, or in forensic investigations.

What is the role of the mu-opioid receptor (MOR) in oxycodone's effects?

Oxycodone is a full agonist of the MOR, meaning it binds to and activates this receptor. This activation is the primary mechanism through which oxycodone exerts its analgesic effects and contributes to the reward pathways associated with its use and potential for addiction.

How does oxycodone's potency compare to morphine when administered intravenously?

When administered intravenously, 10 mg of oxycodone is considered equianalgesic to 10 mg of morphine, indicating similar potency via this route. This contrasts with oral administration, where oxycodone is generally considered more potent.

What are the potential neurological consequences of severe oxycodone overdose?

Severe oxycodone overdose, particularly due to prolonged hypoxia resulting from suppressed breathing, can lead to ischemic damage to the brain and spinal cord infarction. These are serious neurological complications.

What is the significance of the 1961 Single Convention on Narcotic Drugs regarding oxycodone?

The 1961 Single Convention on Narcotic Drugs categorized oxycodone under Schedule I, establishing strict international controls. These controls limit its use to medical and scientific purposes and mandate medical prescriptions for its distribution.

How does the non-medical use of oxycodone in Australia compare to other countries?

By 2015, a significant majority (91%) of injecting drug users sampled in Australia reported using oxycodone, with a notable percentage having injected it recently. This indicates a substantial problem with non-medical use in Australia, similar to trends observed elsewhere.

What is the primary concern regarding the long-term effects of constipation caused by oxycodone?

Chronic constipation induced by oxycodone can become severe and has been linked to life-threatening conditions such as bowel perforations. Managing this side effect is crucial for patients on long-term opioid therapy.

What is the IUPAC name for oxycodone?

The IUPAC name for oxycodone is (5R,9R,13S,14S)-4,5α-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one.

What is the primary enzyme responsible for the N-demethylation of oxycodone?

The primary enzyme responsible for the N-demethylation of oxycodone, converting it to noroxycodone, is CYP3A4. This pathway accounts for a significant portion of its metabolism.

What is the primary enzyme responsible for the O-demethylation of oxycodone?

The O-demethylation of oxycodone to oxymorphone is predominantly carried out by the CYP2D6 enzyme. This metabolic step is important as oxymorphone is an active metabolite.

What is the clinical relevance of oxycodone's lack of immunosuppressive activity compared to morphine?

Unlike morphine, oxycodone has not shown immunosuppressive activity in vitro. The clinical significance of this difference is not fully clarified but might relate to immune system responses during long-term treatment.

How does the bioavailability of intranasal oxycodone compare to oral administration?

Intranasal administration of oxycodone has a bioavailability of approximately 77%, which is comparable to oral administration. However, intranasal use achieves faster peak plasma levels (Tmax).

What are the potential issues with chronic opioid use regarding hormone levels?

Chronic use of opioids like oxycodone can lead to hypogonadism, characterized by reduced sex hormone levels. This condition can have various implications for a patient's overall health and well-being.

What is the role of naloxone when combined with oxycodone?

When combined with oxycodone, naloxone is typically formulated in managed-release tablets to deter abuse and to counteract opioid-induced constipation. Naloxone acts as an opioid antagonist.

What is the historical context of oxycodone's use during World War I?

During World War I, intravenous and intramuscular administrations of oxycodone were commonly used in Germany for postoperative pain management of soldiers, highlighting its early application in military medicine.

What is the significance of the "Miracle Drug of the 1930s" designation for oxycodone in Europe?

The designation "Miracle Drug of the 1930s" for oxycodone in Europe reflects its perceived high efficacy and widespread positive reception during that decade, particularly for its potent analgesic and euphoric properties.

Oxycodone Wiki: Oxycodone: A Comprehensive Pharmacological Overview

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Defining Oxycodone

Opioid Analgesic

Oxycodone is a semi-synthetic opioid medication primarily utilized for the medical management of moderate to severe pain. It is recognized for its efficacy but also carries a significant risk of addiction and abuse.

Potency and Formulation

It is approximately 1.5 times more potent than morphine when administered orally. Available in immediate-release (IR) and extended-release (ER) formulations, it caters to different pain management needs.

Legal Classification

Globally and nationally, oxycodone is classified as a controlled substance (e.g., Schedule II in the US, Class A in the UK) due to its high potential for dependence and abuse.

Medical Applications

Pain Management

Oxycodone is prescribed for moderate to severe acute or chronic pain when alternative treatments are insufficient. Its controlled-release forms are particularly noted for managing cancer pain and pain following major surgery.

Formulation Variety

Available forms include immediate-release tablets and oral solutions, as well as extended-release formulations designed for sustained pain relief over 10-12 hours. Combination products with paracetamol, ibuprofen, naloxone, or aspirin are also common.

Off-Label Use

While primarily for pain, oxycodone formulations (often with naloxone) are sometimes used off-label for severe, refractory restless legs syndrome.

Adverse Effects Profile

Common Side Effects

Frequently reported effects include euphoria, constipation, nausea, vomiting, drowsiness, dizziness, dry mouth, and sweating. Respiratory depression is a significant risk, especially at higher doses.

Dependence and Withdrawal

High potential for physical dependence and addiction exists. Abrupt cessation can lead to severe withdrawal symptoms, including anxiety, insomnia, muscle pain, and flu-like symptoms. Gradual tapering is medically advised.

Serious Risks

Overdose can result in respiratory arrest, coma, and death. Chronic use can lead to hypogonadism. Opioid-induced constipation can become severe, potentially causing bowel perforation.

Pharmacological Mechanisms

Receptor Agonism

Oxycodone functions as a potent and selective full agonist primarily at the μ-opioid receptor (MOR). This interaction modulates neurotransmitter release, influencing pain perception and reward pathways.

Metabolism and Metabolites

Metabolized extensively in the liver by CYP3A4 and CYP2D6 enzymes. Key metabolites include noroxycodone and oxymorphone, which also exhibit MOR activity, though oxycodone itself accounts for the majority of the analgesic effect.

Major metabolic pathways:

N-demethylation to noroxycodone (via CYP3A4).
O-demethylation to oxymorphone (via CYP2D6).
6-Ketoreduction to oxycodols.

Noroxycodone and noroxymorphone have lower blood-brain barrier penetration, limiting their central analgesic contribution despite potential receptor affinity.

Pharmacokinetics

Oral bioavailability ranges from 60-87%. Onset of action for IR forms is 10-30 minutes, with peak plasma levels around 30-60 minutes. Elimination half-life is approximately 4.5 hours for ER formulations.

Key Pharmacokinetic Parameters
Parameter	Value
Bioavailability (Oral)	60–87%
Protein Binding	45%
Tmax (IR)	0.5–1 hour
Tmax (ER)	~3 hours
Half-life (IR)	2–3 hours
Half-life (ER)	4.5 hours
Excretion	Primarily via urine (83%)

Historical Context

Synthesis and Early Use

First synthesized in Germany in 1916 from thebaine. It saw medical application during World War I and was introduced to the US market in 1939. Initially lauded as a significant advancement in pain relief.

Regulatory Milestones

Classified under international drug control conventions and national laws (e.g., US Controlled Substances Act Schedule II). Its formulation history includes the development of extended-release versions like OxyContin in the 1990s.

Societal Impact

Oxycodone's widespread use and abuse have been central to the opioid crisis in various countries, leading to significant public health challenges, legal actions against manufacturers, and regulatory reforms.

Legal and Regulatory Status

International Controls

Subject to international treaties like the Single Convention on Narcotic Drugs (1961), classifying it under Schedule I, mandating strict controls for medical and scientific purposes only.

United States Regulations

Classified as a Schedule II controlled substance under the Controlled Substances Act, indicating a high potential for abuse but accepted medical use with severe restrictions.

UK Classification

Designated as a Class A drug under the Misuse of Drugs Act 1971, reflecting the highest level of control and penalties for illicit activities.

Australian Scheduling

Listed as Schedule 8 (Controlled Drug) in the Poisons Standard, requiring significant restrictions on manufacture, supply, and use to mitigate abuse and dependence.

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References

Analgesic Expert Group. Therapeutic Guidelines: Analgesic. Version 4. Melbourne: Therapeutic Guidelines Ltd, 2007.

William S Burroughs 1952 letter to Allen Ginsburg concerning Eukodal, in Collected Correspondance, pp 141â2

Misuse of Drugs Act (Cap. 185, 2008 Rev. Ed.) (Singapore), section 6(1).

A full list of references for this article are available at the Oxycodone Wikipedia page

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Professional Guidance

This document was generated by an AI and is intended solely for informational and educational purposes, targeting an audience with advanced academic backgrounds. The content is derived from publicly available data and may not be exhaustive or entirely current.

This is not medical advice. The information presented herein should not substitute for professional medical consultation, diagnosis, or treatment. Always consult with a qualified healthcare provider for any health concerns or before making any decisions related to your health or treatment. Reliance on any information provided in this document is solely at your own risk.

The creators assume no responsibility for errors, omissions, or actions taken based on the information provided.

Oxycodone: A Pharmacological Deep Dive

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Defining Oxycodone ℹ️

💊 Opioid Analgesic

📈 Potency and Formulation

⚖️ Legal Classification

Medical Applications ⚕️

🩹 Pain Management

🔄 Formulation Variety

❓ Off-Label Use

Adverse Effects Profile ⚠️

😵 Common Side Effects

🔗 Dependence and Withdrawal

💔 Serious Risks

Pharmacological Mechanisms ⚙️

🎯 Receptor Agonism

🧪 Metabolism and Metabolites

⏳ Pharmacokinetics

Historical Context 📜

💡 Synthesis and Early Use

🏛️ Regulatory Milestones

🌍 Societal Impact

Legal and Regulatory Status ⚖️

📜 International Controls

🇺🇸 United States Regulations

🇬🇧 UK Classification

🇦🇺 Australian Scheduling

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References

📜 References

Feedback & Support 👍

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Important Disclaimer ⚠️

📜 Professional Guidance

Dive in with Flashcard Learning!

Defining Oxycodone

Opioid Analgesic

Potency and Formulation

Legal Classification

Medical Applications

Pain Management

Formulation Variety

Off-Label Use

Adverse Effects Profile

Common Side Effects

Dependence and Withdrawal

Serious Risks

Pharmacological Mechanisms

Receptor Agonism

Metabolism and Metabolites

Pharmacokinetics

Historical Context

Synthesis and Early Use

Regulatory Milestones

Societal Impact

Legal and Regulatory Status

International Controls

United States Regulations

UK Classification

Australian Scheduling

Teacher's Corner

True or False?

Test Your Knowledge!

Gamer's Corner

Discover other topics to study!

References

Feedback & Support

Important Disclaimer

Professional Guidance