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Oxycodone

Note: Since these substances are related, please refer to Codeine Facts for more information on precautions, interactions, mechanism of action and effects.

Facts

Oxycodone is a semisynthetic opiate agonist derived from the opioid alkaloid, thebaine, and is similar to other phenanthrene derivatives such as hydrocodone and morphine. Oxycodone is used to control moderate to severe pain, including cancer pain, postoperative, postextractional, and postpartum pain and non-pain syndromes such as restless leg and Tourette syndromes. Oxycodone has the same potency as morphine (but considerably less side effects) and may be an alternative in users or patients who can not tolerate morphine or hydromorphone.

Listen to the correct pronunciation of the word oxycodone.

Precautions

Related information: codeine precautions

Interactions

Related information: codeine interactions

Administration

Oxycodone can be administered orally (most effective), intramuscularly, subcutaneously (skin popping), intravenously, intranasally (sniffing or snorting), rectally and transdermally (eg by skin patches).

Intravenous administration is associated with rapid onset (5 minutes) of the effects and a short duration, while rectal administration provides longer onset (30-60 minutes) of the effects and up to 3 times longer duration, although there is no difference in the potency.

Dosage

Related information: codeine dosage

Metabolism

Oxycodone is about 45% protein bound. Once absorbed, oxycodone is distributed to skeletal muscle, liver, intestinal tract, lungs, spleen, and the CNS. Oxycodone has been found in breast milk. Metabolism of oxycodone occurs in the liver with excretion principally in the urine. Oxycodone is metabolised to noroxycodone. Conversion to oxymorphone is mediated by the cytochrome P450-2D6 (CYP2D6).

Oxycodone is excreted mainly as a conjugate whereas noroxycodone mostly in an unconjugated form. The plasma half-life is 3-5 hours.

Effects

The effects start in 10-30 minutes. Peak effects occur in 60-90 minutes and last for 4-6 hours.

Oxycodone has been reported to be as effective as morphine in relieving pain when given in equianalgesic doses and to cause less nausea, vomiting and hallucinations.

Effects are up to 8 times more potent than those of codeine. Oxycodone is similar to codeine and methadone in that it retains at least one half of its analgesic activity when administered orally.

Extraction

With oxycodone tablets that may include other substances, such as paracetamol, the extraction method is the same as with codeine.

Drug testing

Following the administration of oxycodone, the following substances can be detected up to 72 hours after (depends upon the dose, its frequency, route of administration and urine excretion/dilution): oxycodone and oxymorphone.

Opioids can be detected in urine, blood, bile, hair, nails and sweat.

Chemistry

Oxycodone differs structurally from hydrocodone only in the attachment of a hydroxyl group to carbon 14 on the phenanthrene nucleus.

Oxycodone 2D molecule
NameOxycodone
Chemical name4,5-alpha-epoxy-14-hydroxy-3-methoxy-17-methyl-Morphinan-6-one
Alternative chemical namesdihydrohydroxycodeinone, 14-hydroxydihydrocodeinone
CAS Number000076-42-6
Chemical formulaC18H21NO4
Molecular weight315.40
Melting point218-220C

Oxycodone occurs as white crystalline powder (long rods or as tautomeric, strongly refringent scales). Oxycodone is well soluble in alcohol (1g of oxycodone hydrochloride in 60ml of ethyl alcohol) and chloroform, nearly soluble in ammonia, ether, water, potassium and sodium hydroxide. Oxycodone is commercially available as the hydrochloride salt or in combination preparations as the hydrochloride and the terephthalate salts. Oxycodone hydrochloride preparations should be stored in tight containers and generally should be protected from light and stored at 15-30C.

NameOxycodone hydrochloride
Chemical name4,5-alpha-epoxy-14-hydroxy-3-methoxy-17-methyl-Morphinan-6-one hydrochloride
Alternative namesdihydrohydroxycodeinone hydrochloride, 14-hydroxydihydrocodeinone hydrochloride
CAS Number124-90-3
Chemical formulaC18H21NO4.HCl
Molecular weight351.86
pHca 1.4-4 (oral solution)

Related information: 3D oxycodone molecule

Synthesis/Conversions