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Oxycodone

Medical Uses and Forms: – Used for managing moderate to severe acute or chronic pain. – Improves quality of life in certain types of pain. […]

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Medical Uses and Forms:
– Used for managing moderate to severe acute or chronic pain.
– Improves quality of life in certain types of pain.
– Controlled-release tablet available for every 12 hours.
– Valid alternative to morphine for cancer pain.
– FDA approved for children with specific pain conditions.
– Available in immediate-release and controlled-release formulations.
– Various combinations with paracetamol, aspirin, ibuprofen, naloxone, naltrexone.
– Liquid solution available.
– Parenteral formulations in some regions.
– Historical use in IV and IM administrations.

Side Effects, Dependence, and Withdrawal:
– Common side effects include constipation, nausea, vomiting, dizziness.
– Chronic use may lead to serious constipation issues.
– Medications developed to address opioid-induced constipation.
– High risk of severe withdrawal symptoms with abrupt discontinuation.
– Withdrawal symptoms include anxiety, muscle pain, flu-like symptoms.
– Regular recreational or high-dose users at higher risk of severe withdrawal.
– Gradual withdrawal recommended for extended use.

Hormone Levels and Interactions:
– Chronic use can cause low sex hormone levels.
– Higher doses increase the risk of hypogonadism.
– Concurrent hypogonadism a common issue with chronic use.
– Opioid-induced low sex hormone levels a known effect.
– Regular monitoring of hormone levels recommended.
– Metabolized by CYP3A4 and CYP2D6 enzymes.
– Clearance of oxycodone can be altered by inhibitors and inducers of these enzymes.
– Natural genetic variation in these enzymes can influence oxycodone clearance.
– Ritonavir and lopinavir/ritonavir increase plasma concentrations of oxycodone.
– Rifampicin reduces plasma concentrations of oxycodone.

Pharmacology, Pharmacodynamics, and Active Metabolites:
– Equianalgesic doses of oxycodone compared to other opioids.
– Oxycodone is a selective full agonist of the μ-opioid receptor.
– Oxycodone inhibits neurotransmitter release by decreasing cAMP and opening potassium channels.
– Oxycodone’s analgesic effects are attributed to MOR activation in specific brain regions.
– Metabolites of oxycodone can also act as MOR agonists.
– Oxymorphone has higher affinity and efficacy at the MOR compared to oxycodone.
– Noroxycodone and noroxymorphone have longer half-lives and lower analgesic effects.
– Unchanged oxycodone is the main contributor to analgesia despite metabolite formation.

Chemistry, Biosynthesis, History, Metabolism, and Regulation:
– Oxycodone’s chemical structure and similarity to codeine.
– Biosynthesis methods involving microbial compound manufacturing.
– History of synthesis and development dating back to the early 20th century.
– Metabolism mainly occurs in the liver via the cytochrome P450 system.
– Oxycodone classified as a Schedule II controlled substance.
– Development, introduction, and regulation of oxycodone, including its commercial use.
– Impact of oxycodone on the opioid epidemic, including misuse, overdose deaths, and emergency room visits.

Oxycodone (Wikipedia)

Oxycodone, sold under various brand names such as Roxicodone and OxyContin (which is the extended release form), is a semi-synthetic opioid used medically for treatment of moderate to severe pain. It is highly addictive and is a commonly abused drug. It is usually taken by mouth, and is available in immediate-release and controlled-release formulations. Onset of pain relief typically begins within fifteen minutes and lasts for up to six hours with the immediate-release formulation. In the United Kingdom, it is available by injection. Combination products are also available with paracetamol (acetaminophen), ibuprofen, naloxone, naltrexone, and aspirin.

Oxycodone
Clinical data
Pronunciation/ɒksiˈkdn/
Trade namesOxyContin, Endone, others
Other namesEukodal, eucodal; dihydrohydroxycodeinone, 7,8-dihydro-14-hydroxycodeinone, 6-deoxy-7,8-dihydro-14-hydroxy-3-O-methyl-6-oxomorphine
AHFS/Drugs.comMonograph
MedlinePlusa682132
License data
Pregnancy
category
  • AU: C
Dependence
liability
High
Addiction
liability
High
Routes of
administration
By mouth, sublingual, intramuscular, intravenous, intranasal, subcutaneous, transdermal, rectal, epidural
Drug classOpioid
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityBy mouth: 60–87%
Protein binding45%
MetabolismLiver: mainly CYP3A, and, to a much lesser extent, CYP2D6 (~5%); 95% metabolized (i.e., 5% excreted unchanged)
MetabolitesNoroxycodone (25%)
Noroxymorphone (15%, free and conjugated)
Oxymorphone (11%, conjugated)
• Others (e.g., minor metabolites)
Onset of actionIRTooltip Instant release: 10–30 minutes
CRTooltip controlled release: 1 hour
Elimination half-lifeBy mouth (IR): 2–3 hrs (same t1/2Tooltip biological half-life for all ROAsTooltip routes of administration)
By mouth (CR): 4.5 hrs
Duration of actionBy mouth (IR): 3–6 hrs
By mouth (CR): 10–12 hrs
ExcretionUrine (83%)
Identifiers
  • (5R,9R,13S,14S)-4,5α-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.874 Edit this at Wikidata
Chemical and physical data
FormulaC18H21NO4
Molar mass315.369 g·mol−1
3D model (JSmol)
Melting point219 °C (426 °F)
Solubility in water166 (HCl)
  • O=C4[C@@H]5Oc1c2c(ccc1OC)C[C@H]3N(CC[C@]25[C@@]3(O)CC4)C
  • InChI=1S/C18H21NO4/c1-19-8-7-17-14-10-3-4-12(22-2)15(14)23-16(17)11(20)5-6-18(17,21)13(19)9-10/h3-4,13,16,21H,5-9H2,1-2H3/t13-,16+,17+,18-/m1/s1 checkY
  • Key:BRUQQQPBMZOVGD-XFKAJCMBSA-N checkY
  (verify)

Common side effects include euphoria, constipation, nausea, vomiting, loss of appetite, drowsiness, dizziness, itching, dry mouth, and sweating. Side effects may also include addiction and dependence, substance abuse, irritability, depression or mania, delirium, hallucinations, hypoventilation, gastroparesis, bradycardia, and hypotension. Those allergic to codeine may also be allergic to oxycodone. Use of oxycodone in early pregnancy appears relatively safe. Opioid withdrawal may occur if rapidly stopped from withdrawal. Oxycodone acts by activating the μ-opioid receptor. When taken by mouth, it has roughly 1.5 times the effect of the equivalent amount of morphine.

Oxycodone was originally produced from the opium poppy opiate alkaloid thebaine in 1916. It was first used medically in Germany in 1917. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2021, it was the 59th most commonly prescribed medication in the United States, with more than 11 million prescriptions. A number of abuse-deterrent formulations are available, such as in combination with naloxone or naltrexone.

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