General
Preferred name
OXYCODONE
Synonyms
OXYCODONE HYDROCHLORIDE ()
OXYCODONE TEREPHTHALATE ()
PTI-821 ()
Pavinal ()
NSC-19043 ()
Oxycontin ()
Oxycodone cii ()
PF-00345439 ()
Proladone ()
Oxicone ()
Xtampza ER ()
Pti 821 ()
(-)-14-hydroxydihydrocodeinone ()
Oxymorphone 3-methyl ether ()
Remoxy ()
Xtampza ()
Dihydrone ()
IDS-NO-002 ()
N02AA05 ()
14-hydroxydihydrocodeinone ()
Reltebon ()
Oxylan ()
Anhydrous oxycodone hydrochloride ()
Candox ()
Dolocodon PR ()
Shortec ()
Oxaydo ()
Oxycodone hydrochloride cii ()
Leveraxo ()
Oxycodone hcl ()
Roxicodone ()
Abtard ()
Oxecta ()
Carexil ()
Lynlor ()
Oxeltra ()
Longtec ()
Endocodone ()
Oxynorm ()
Zomestine ()
Roxybond ()
Oxycodone-d6 (CRM) ()
Oxycodone-d3 ()
Oxycodone (hydrochloride) ()
P&D ID
PD009992
CAS
76-42-6
25333-72-6
124-90-3
152477-91-3
145225-02-1
Tags
drug
natural product
biased GPCR ligand
available
Approved by
PMDA
FDA
First approval
1950
Drug Status
illicit
investigational
approved
withdrawn
Drug indication
Analgesic (narcotic)
Chronic pain
Back pain
Pain
Max Phase
Phase 4
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
MOA
The full mechanism of oxycodone is not known.[Label] 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.[A178696] Oxycodone and its active metabolites, noroxycodone, oxymorphone, and noroxymorphone are opioid agonists.[A178639] These compounds passively diffuse across the blood brain barrier or may be actively transported across by an unknown mechanism.[A178696] 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.[A178696] Activation of mu opioid receptors inhibits N-type voltage operated calcium channels, inhibiting responses to pain.[A178735]
INDICATION
Oxycodone is indicated for the treatment of moderate to severe pain.[Label] There is also an extended release formulation indicated for chronic moderate to severe pain requiring continuous opioid analgesics for an extended period.[Label]
ROE
Oxycodone is mainly eliminated in the urine.[Label] Unbound noroxycodone makes up 23% of the dose recovered in urine and oxymorphone makes up <1%.[Label] conjugated oxymorphone makes up 10% of the recovered dose.[Label] Free and conjugated oxycodone makes up 8.9% of the recovered dose, noroxymorphone makes up 14%, and reduced metabolites make up 18%.[Label]
METABOLISM
Oxycodone's metabolism is hepatic 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.[A178639]; ; Oxycodone is metabolized by CYP3A4 and CYP3A5 to noroxycodone and then by CYP2D6 to noroxymorphone.[A178639] Noroxycodone and noroxymorphone are the primary circulating metabolites.[Label] Noroxycodone can also be 6-keto-reduced to alpha or beta noroxycodol.[A178639]; ; Oxycodone can be metabolized by CYP2D6 to oxymorphone and then by CYP3A4 to noroxymorphone.[A178639] Oxymorphone can also be 6-keto-reduced to alpha or beta oxymorphol.[A178639]; ; Oxycodone can also be 6-keto-reduced to alpha and beta oxycodol.[A178639]; ; The active metabolites noroxycodone, oxymorphone, and noroxymorphone can all be conjugated before elimination.[A178639]
HALF-LIFE
The apparent elimination half life of oxycodone is 3.2 hours for immediate release formulations and 4.5 hours for extended release formulations.[Label] Noroxycodone has a half life of 5.8 hours, oxymorphone has a half life of 8.8 hours, noroxymorphone has a half life of 9 hours.[A178639]
ABSORPTION
Oxycodone has an oral bioavailability of 60% to 87% that is unaffected by food.[Label]; ; 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.[Label]
DESCRIPTION
Oxycodone is an opioid drug.
(GtoPdb)
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.[Label] Oxycodone's effect on the respiratory centre is dose dependant respiratory depression.[Label] The action on the cough centre is suppression of the cough reflex.[Label] Pupils become miopic or decrease in size, peristalsis of the gastrointestinal tract slows, and muscle tone in the colon may increase causing constipation.[Label] In the cardiovascular system histamine may be released leading to pruritis, red eyes, flushing, sweating, and decreased blood pressure.[Label] Endocrine effects may include increased prolactin, decreased cortisol, and decreased testosterone.[Label] It is not yet known if the effects of opioids on the immune system are clinically significant.[Label]
TOXICITY
Patients experiencing an overdose may present with respiratory depression, sleepiness, stupor, coma, skeletal muscle flaccidity, cold sweat, constricted pupils, bradycardia, hypotension, partial or complete airway obstruction, atypical snoring, and death.[Label] Overdose should be treated by maintaining airway, ventilation, and oxygenation.[Label] Oxygen and vasopressor treatment may be necessary to treat circulatory shock and pulmonary edema and defibrillation may be required for cardiac arrest of arrhythmia.[Label] [Naloxone], [nalmefene], or [naltrexone] may be used to counteract the effects of opioids but patients should be monitored in case further doses are required.[Label]; ; The intraperitoneal LD50 in mice is 320mg/kg, the oral LD50 is 426mg/kg.[MSDS] The oral lowest dose causing toxic effects in humans is 0.14mg/kg and subcutaneously in rats it is 1.53mg/kg.[MSDS]; ; Oxycodone is pregnancy category B according to the FDA.[Label] There is a paucity of data regarding oxycodone use in pregnancy, though animal studies show no teratogenic effects.[Label] Rats given oxycodone during lactation showed smaller offspring, though after lactation, they recovered to normal size.[Label] Oxycodone is excreted in breast milk and so patients should not breastfeed while taking oxycodone due to risk of sedation and respiratory depression in infants.[Label]; ; No studies on the carcinogenicity of oxycodone have been performed.[Label] Oxycodone was genotoxic at 50mcg/mL with metabolic activation and at 400mcg/mL without.[Label] It was also clastogenic with metabolic activation at â¥1250mcg/mL.[Label] Oxycodone was not found to be genotoxic in other tests.[Label] Oxycodone does not affect reproduction and fertility in rats at doses of up to 8mg/kg/day.[Label]
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Compound Sets
16
BiasDB
ChEMBL Approved Drugs
ChEMBL Drugs
DrugBank
DrugBank Approved Drugs
DrugCentral
DrugCentral Approved Drugs
DrugMAP Approved Drugs
Guide to Pharmacology
NCATS Inxight Approved Drugs
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Other bioactive compounds
ReFrame library
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
83
Molecular Weight
315.15
Hydrogen Bond Acceptors
5
Hydrogen Bond Donors
1
Rotatable Bonds
1
Ring Count
5
Aromatic Ring Count
1
cLogP
1.05
TPSA
59.0
Fraction CSP3
0.61
Chiral centers
4.0
Largest ring
6.0
QED
0.84
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Member status
virtual
MOA
Opioid Receptor Agonists
Therapeutic Class
Analgesics
Source data
