Description

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summary

Oxycodone is an opioid used in the management of moderate to severe pain.

Brand Names

Endocet, Endodan Reformulated May 2009, Nalocet, Oxaydo, Oxy.IR, Oxycontin, Oxyneo, Percocet, Prolate, Rivacocet, Roxicet, Roxicodone, Targin, Targiniq, Xolox, Xtampza

Generic Name

Oxycodone

DrugBank Accession Number

DB00497

Background

Oxycodone is a semisynthetic opioid analgesic derived from thebaine in Germany in 1917.³ It is currently indicated as an immediate release product for moderate to severe pain and as an extended-release product for chronic moderate to severe pain requiring continuous opioid analgesics for an extended period.^Label The first oxycodone containing product, Percodan, was approved by the FDA on April 12, 1950.⁵

Type

Small Molecule

Groups

Approved, Illicit, Investigational

Structure

Similar Structures

Weight

Average: 315.3636
Monoisotopic: 315.147058165

Chemical Formula

C₁₈H₂₁NO₄

Synonyms

• Dihydrohydroxycodeinone
• Dihydroxycodeinone
• Oxicodona
• Oxycodone
• Oxycodonum

External IDs

• IDS-NO-002
• N02AA05
• NSC-19043
• PF-00345439
• PTI-821

PHARMACOLOGY

Indication

Oxycodone is indicated for the treatment of moderate to severe pain.There is also an extended-release formulation indicated for chronic moderate to severe pain requiring continuous opioid analgesics for an extended period

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Associated Conditions

• Severe Pain
• Severe, Chronic Pain
• Acute, moderate Pain
• Chronic, moderate Pain
• Severe Pain, Acute

Contraindications & Blackbox Warnings

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Pharmacodynamics

Oxycodone acts directly on a number of tissues not related to its analgesic effect. These tissues include the respiratory centre in the brain stem, the cough centre in the medulla, muscles of the pupils, gastrointestinal tract, cardiovascular system, endocrine system, and immune system.Oxycodone’s effect on the respiratory centre is dose dependant respiratory depression. The action on the cough centre is suppression of the cough reflex.Pupils become miopic or decrease in size, peristalsis of the gastrointestinal tract slows, and muscle tone in the colon may increase causing constipation.In the cardiovascular system histamine may be released leading to pruritis, red eyes, flushing, sweating, and decreased blood pressure.Endocrine effects may include increased prolactin, decreased cortisol, and decreased testosterone. It is not yet known if the effects of opioids on the immune system are clinically significant.

Mechanism of action

The full mechanism of oxycodone is not known,Under conditions of inflammation or hyperalgesia, opioid receptors in the heart, lungs, liver, gastrointestinal tract, and reproductive system are upregulated and transported to nerve terminals.Oxycodone and its active metabolites, noroxycodone, oxymorphone, and noroxymorphone are opioid agonists. These compounds passively diffuse across the blood brain barrier or may be actively transported across by an unknown mechanism. Oxycodone and its active metabolites can selectively bind to the mu opioid receptor, but also the kappa and delta opioid receptors in the central nervous system and periphery, and induce a G protein coupled receptor signalling pathway. Activation of mu opioid receptors inhibits N-type voltage operated calcium channels, inhibiting responses to pain.

TARGET	ACTIONS	ORGANISM
AMu-type opioid receptor	agonist	Humans
AKappa-type opioid receptor	agonist	Humans
ADelta-type opioid receptor	agonist	Humans

Absorption

Oxycodone has an oral bioavailability of 60% to 87% that is unaffected by food.

The area under the curve is 135ng/mL*hr, maximum plasma concentration is 11.5ng/mL, and time to maximum concentration is 5.11hr in patients given a 10mg oral immediate release dose of oxycodone.

Volume of distribution

2.6L/kg.

Protein binding

45%.Oxycodone is primarily bound to serum albumin and to a lesser degree alpha1-acid glycoprotein.

Metabolism

Oxycodone’s hepatic metabolism is extensive and completed by 4 main reactions. CYP3A4 and 3A5 perform N-demethylation, CYP2D6 performs O-demethylation, unknown enzymes perform 6-keto-reduction, and unknown enzymes perform conjugation.

Oxycodone is metabolized by CYP3A4 and CYP3A5 to noroxycodone and then by CYP2D6 to noroxymorphone.Noroxycodone and noroxymorphone are the primary circulating metabolites. Noroxycodone can also be 6-keto-reduced to alpha or beta noroxycodol.

Oxycodone can be metabolized by CYP2D6 to oxymorphone and then by CYP3A4 to noroxymorphone.Oxymorphone can also be 6-keto-reduced to alpha or beta oxymorphol.

Oxycodone can also be 6-keto-reduced to alpha and beta oxycodol.

The active metabolites noroxycodone, oxymorphone, and noroxymorphone can all be conjugated before elimination.

 

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