Oxycodone

Identification

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, Roxybond, 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
Weight
Average: 315.3636
Monoisotopic: 315.147058165
Chemical Formula
C18H21NO4
Synonyms
  • (-)-14-Hydroxydihydrocodeinone
  • 4,5-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
  • 4,5alpha-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
  • 4,5α-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-one
  • Dihydro-14-hydroxycodeinone
  • 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.Label There is also an extended release formulation indicated for chronic moderate to severe pain requiring continuous opioid analgesics for an extended period.Label

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofSevere acute pain••••••••••••
Management ofSevere chronic pain••••••••••••
Management ofSevere pain•••••••••••••••••••• •••••••• •••••••
Used in combination to manageSevere painMixture Product in combination with: Acetaminophen (DB00316), Ibuprofen (DB01050), Naproxen (DB00788)••••••••••••
Management ofModerate acute pain••••••••••••
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.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

Mechanism of action

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.3 Oxycodone and its active metabolites, noroxycodone, oxymorphone, and noroxymorphone are opioid agonists.1 These compounds passively diffuse across the blood brain barrier or may be actively transported across by an unknown mechanism.3 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.3 Activation of mu opioid receptors inhibits N-type voltage operated calcium channels, inhibiting responses to pain.4

TargetActionsOrganism
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.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

Volume of distribution

2.6L/kg.Label

Protein binding

45%.Label Oxycodone is primarily bound to serum albumin and to a lesser degree alpha1-acid glycoprotein.2

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.1

Oxycodone is metabolized by CYP3A4 and CYP3A5 to noroxycodone and then by CYP2D6 to noroxymorphone.1 Noroxycodone and noroxymorphone are the primary circulating metabolites.Label Noroxycodone can also be 6-keto-reduced to alpha or beta noroxycodol.1

Oxycodone can be metabolized by CYP2D6 to oxymorphone and then by CYP3A4 to noroxymorphone.1 Oxymorphone can also be 6-keto-reduced to alpha or beta oxymorphol.1

Oxycodone can also be 6-keto-reduced to alpha and beta oxycodol.1

The active metabolites noroxycodone, oxymorphone, and noroxymorphone can all be conjugated before elimination.1

Hover over products below to view reaction partners

Route of elimination

Oxycodone and its metabolites are 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

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.1

Clearance

Total plasma clearance is 1.4L/min in adults.Label

Adverse Effects
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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 ≥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

Pathways
PathwayCategory
Oxycodone Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Oxycodone is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Oxycodone can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Oxycodone can be increased when combined with Abatacept.
AbirateroneThe metabolism of Oxycodone can be decreased when combined with Abiraterone.
AcalabrutinibThe metabolism of Oxycodone can be decreased when combined with Acalabrutinib.
Food Interactions
  • Avoid alcohol.
  • Take with or without food. Food does not significantly affect absorption.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Oxycodone hydrochlorideC1ENJ2TE6C124-90-3MUZQPDBAOYKNLO-RKXJKUSZSA-N
Oxycodone terephthalateM04XWV43UF124133-68-2BTEYIHUKHHAVAN-KDKWOIFOSA-N
Product Images
International/Other Brands
Oxanest / OxyIR
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act Oxycodone CRTablet, extended release40 mgOralTEVA Canada Limited2012-11-262020-06-11Canada flag
Act Oxycodone CRTablet, extended release5 mgOralTEVA Canada Limited2012-11-262020-06-11Canada flag
Act Oxycodone CRTablet, extended release20 mgOralTEVA Canada Limited2012-11-262020-06-11Canada flag
Act Oxycodone CRTablet, extended release80 mgOralTEVA Canada Limited2012-11-262020-06-11Canada flag
Act Oxycodone CRTablet, extended release10 mgOralTEVA Canada Limited2012-11-262020-06-11Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-oxycodone CRTablet, extended release60 mgOralApotex Corporation2012-11-27Not applicableCanada flag
Apo-oxycodone CRTablet, extended release20.0 mgOralApotex Corporation2012-11-26Not applicableCanada flag
Apo-oxycodone CRTablet, extended release40 mgOralApotex Corporation2012-11-26Not applicableCanada flag
Apo-oxycodone CRTablet, extended release15 mgOralApotex Corporation2012-11-27Not applicableCanada flag
Apo-oxycodone CRTablet, extended release5.0 mgOralApotex Corporation2012-11-26Not applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Apo-oxycodone/acetOxycodone hydrochloride (5 mg) + Acetaminophen (325 mg)TabletOralApotex Corporation2009-04-15Not applicableCanada flag
APOKLISIOxycodone hydrochloride (10 MG) + Naloxone hydrochloride (5 MG)Tablet, extended releaseOralNeopharmed Gentili S.P.A.2020-10-132022-06-24Italy flag
APOKLISIOxycodone hydrochloride (5 MG) + Naloxone hydrochloride (2.5 MG)Tablet, extended releaseOralNeopharmed Gentili S.P.A.2020-10-132022-06-24Italy flag
APOKLISIOxycodone hydrochloride (10 MG) + Naloxone hydrochloride (5 MG)Tablet, extended releaseOralNeopharmed Gentili S.P.A.2020-05-282024-03-03Italy flag
APOKLISIOxycodone hydrochloride (10 MG) + Naloxone hydrochloride (5 MG)Tablet, extended releaseOralNeopharmed Gentili S.P.A.2020-05-282024-03-03Italy flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Oxycodone HydrochlorideOxycodone hydrochloride (20 mg/1mL)Solution, concentrateOralMallinckrodt2009-06-022011-10-31US flag
Oxycodone HydrochlorideOxycodone hydrochloride (20 mg/1mL)Solution, concentrateOralPhysicians Total Care, Inc.2006-01-012011-07-31US flag
Oxycodone HydrochlorideOxycodone hydrochloride (20 mg/1mL)Solution, concentrateOral8282696752013-09-232013-09-23US flag
Oxycodone HydrochlorideOxycodone hydrochloride (20 mg/1mL)Solution, concentrateOralMallinckrodt2009-06-022011-10-31US flag
Oxycodone HydrochlorideOxycodone hydrochloride (5 mg/1)CapsuleOralPhysicians Total Care, Inc.2006-05-082013-01-11US flag

Categories

ATC Codes
N02AA56 — Oxycodone and naltrexoneN02AA05 — OxycodoneN02AA55 — Oxycodone and naloxoneN02AJ18 — Oxycodone and acetylsalicylic acidN02AJ17 — Oxycodone and paracetamolN02AJ19 — Oxycodone and ibuprofen
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenanthrenes and derivatives
Sub Class
Not Available
Direct Parent
Phenanthrenes and derivatives
Alternative Parents
Isoquinolones and derivatives / Tetralins / Coumarans / Anisoles / Alkyl aryl ethers / Aralkylamines / Piperidines / Tertiary alcohols / Trialkylamines / 1,2-aminoalcohols
show 7 more
Substituents
1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Carbonyl group / Coumaran
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heteropentacyclic compound (CHEBI:7852)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
CD35PMG570
CAS number
76-42-6
InChI Key
BRUQQQPBMZOVGD-XFKAJCMBSA-N
InChI
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
IUPAC Name
(1S,5R,13R,17S)-17-hydroxy-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-one
SMILES
COC1=C2O[C@H]3C(=O)CC[C@@]4(O)[C@H]5CC(C=C1)=C2[C@@]34CCN5C

References

Synthesis Reference

Bao-Shan Huang, Yansong Lu, Ben-Yi Ji, Aris P Christodoulou, "Preparation of oxycodone from codeine." U.S. Patent US6008355, issued March, 1990.

US6008355
General References
  1. DePriest AZ, Puet BL, Holt AC, Roberts A, Cone EJ: Metabolism and Disposition of Prescription Opioids: A Review. Forensic Sci Rev. 2015 Jul;27(2):115-45. [Article]
  2. Leow KP, Wright AW, Cramond T, Smith MT: Determination of the serum protein binding of oxycodone and morphine using ultrafiltration. Ther Drug Monit. 1993 Oct;15(5):440-7. [Article]
  3. Ruan X, Mancuso KF, Kaye AD: Revisiting Oxycodone Analgesia: A Review and Hypothesis. Anesthesiol Clin. 2017 Jun;35(2):e163-e174. doi: 10.1016/j.anclin.2017.01.022. Epub 2017 Mar 14. [Article]
  4. Andrade A, Denome S, Jiang YQ, Marangoudakis S, Lipscombe D: Opioid inhibition of N-type Ca2+ channels and spinal analgesia couple to alternative splicing. Nat Neurosci. 2010 Oct;13(10):1249-56. doi: 10.1038/nn.2643. Epub 2010 Sep 19. [Article]
  5. FDA Approved Drug Products: Percodan [Link]
  6. FDA Approved Drug Products: XTAMPZA ER (oxycodone) extended-release capsules, for oral use, CII [Link]
Human Metabolome Database
HMDB0014640
KEGG Drug
D05312
KEGG Compound
C08018
PubChem Compound
5284603
PubChem Substance
46508908
ChemSpider
4447649
BindingDB
50370595
RxNav
7804
ChEBI
7852
ChEMBL
CHEMBL656
ZINC
ZINC000000403533
Therapeutic Targets Database
DAP000283
PharmGKB
PA450741
PDBe Ligand
OOX
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Oxycodone
PDB Entries
7u63
FDA label
Download (238 KB)
MSDS
Download (23.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentConstipation / Postoperative pain1
4Active Not RecruitingTreatmentOocyte Retrieval / Postoperative pain1
4Active Not RecruitingTreatmentOxycodone / Pharmacogenomics / Pharmacokinetics1
4Active Not RecruitingTreatmentPain, Labor1
4Active Not RecruitingTreatmentPostoperative pain1

Pharmacoeconomics

Manufacturers
  • Mallinckrodt inc
  • Purdue pharma lp
  • Roxane laboratories inc
  • Actavis totowa llc
  • Avanthi inc
  • Corepharma llc
  • Kv pharmaceutical co
  • Sun pharmaceutical industries inc
  • Tyco healthcare mallinckrodt
  • Vintage pharmaceuticals inc
  • Xanodyne pharmaceuticals inc
  • Endo Pharmaceuticals
Packagers
  • 4uOrtho LLC
  • Actavis Group
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apotex Inc.
  • Apotheca Inc.
  • Athlon Pharmaceuticals Inc.
  • Atley Pharmaceuticals
  • Barr Pharmaceuticals
  • Blenheim Pharmacal
  • Bristol-Myers Squibb Co.
  • Bryant Ranch Prepack
  • Caraco Pharmaceutical Labs
  • Cardinal Health
  • Chattem Chemicals Inc.
  • Cody Laboratories Inc.
  • Core Pharmaceuticals
  • Corepharma LLC
  • D.M. Graham Laboratories Inc.
  • DAVA Pharmaceuticals
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Dorx LLC
  • DSM Corp.
  • Endo Pharmaceuticals Inc.
  • Endogen
  • Ethex Corp.
  • Forest Pharmaceuticals
  • Glenmark Generics Ltd.
  • Global Pharmaceuticals
  • Impax Laboratories Inc.
  • Ivax Pharmaceuticals
  • Janssen-Ortho Inc.
  • KV Pharmaceutical Co.
  • KVK-Tech Inc.
  • Lake Erie Medical and Surgical Supply
  • Lannett Co. Inc.
  • Lehigh Valley Technologies Inc.
  • Major Pharmaceuticals
  • Mallinckrodt Inc.
  • Mckesson Corp.
  • Metrics Inc.
  • Midlothian Labs
  • Mikart Inc.
  • Mylan
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • Ortho-McNeil-Janssen Pharmaceuticals Inc.
  • P F Laboratories Inc.
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
  • Purdue Pharma LP
  • Qualitest
  • Quality Care
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Rhodes Pharmaceutical LP
  • Roxane Labs
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • Sun Pharmaceutical Industries Ltd.
  • Superior Pharmeceuticals
  • Teva Pharmaceutical Industries Ltd.
  • Ther-Rx Corp.
  • Victory Pharma
  • Vindex Pharmaceuticals Inc.
  • Vintage Pharmaceuticals Inc.
  • Vistapharm Inc.
  • Watson Pharmaceuticals
  • WraSer Pharmaceuticals
  • Xanodyne Pharmaceuticals Inc.
Dosage Forms
FormRouteStrength
Tablet, extended releaseOral5 mg
Tablet, extended releaseOral20.0 mg
Tablet, extended releaseOral40 mg
Tablet, extended releaseOral5.0 mg
Tablet, extended releaseOral80.0 mg
Tablet, extended releaseOral20 MG
Capsule, extended releaseOral
Tablet, effervescentOral
Tablet, extended releaseOral
TabletOral5.000 mg
TabletOral40.000 mg
SolutionIntramuscular; Intravenous; Subcutaneous10 mg
SolutionIntramuscular; Intravenous; Subcutaneous20 mg
SolutionIntravenous10.000 mg
Injection, solutionParenteral10 MG/ML
Injection, solutionParenteral50 MG/ML
TabletOral7.5 mg/1
SolutionIntravenous; Subcutaneous10 mg
Tablet, multilayer, extended releaseOral20 mg
Tablet, extended releaseOral
CapsuleOral
Capsule, gelatin coatedOral
TabletOral
Tablet, coatedOral
CapsuleOral5 mg/1
SolutionOral100 mg/5mL
SolutionOral20 mg/1mL
Solution, concentrateOral20 mg/1mL
TabletOral10 mg/1
TabletOral15 mg/1
TabletOral20 mg/1
TabletOral30 mg/1
TabletOral40 mg/1
TabletOral5 mg/1
TabletOral80 mg/1
Tablet, film coated, extended releaseOral10 mg/1
Tablet, film coated, extended releaseOral20 mg/1
Tablet, film coated, extended releaseOral40 mg/1
Tablet, film coated, extended releaseOral80 mg/1
Tablet, film coatedOral
Tablet, extended releaseOral10 mg/1
Tablet, extended releaseOral20 mg/1
Tablet, extended releaseOral40 mg/1
Tablet, extended releaseOral80 mg/1
Injection, solutionIntravenous; Subcutaneous10.00 mg/mL
TabletOral10.00 mg
Tablet, film coated, extended releaseOral15 mg/1
Tablet, film coated, extended releaseOral160 mg/1
Tablet, film coated, extended releaseOral30 mg/1
Tablet, film coated, extended releaseOral60 mg/1
Tablet, film coated, extended releaseOral10 mg
Tablet, film coated, extended releaseOral40 mg
Tablet, film coated, extended releaseOral5 mg
Tablet, film coated, extended releaseOral80.00 mg
Tablet, delayed releaseOral15 mg
Tablet, delayed releaseOral30 mg
Tablet, delayed releaseOral60 mg
Tablet, delayed releaseOral80 mg
Tablet, film coatedOral10 mg
Tablet, film coatedOral20 mg
Tablet, film coatedOral40 mg
Tablet, film coatedOral5 mg
Tablet, film coatedOral80 mg
Tablet, film coated, extended releaseOral10.0 mg
Tablet, film coated, extended releaseOral20 mg
Tablet, film coated, extended releaseOral60 mg
Tablet, film coated, extended releaseOral80 mg
Tablet, extended releaseOral120 MG
Tablet, extended releaseOral15 mg
Tablet, extended releaseOral30 mg
Tablet, extended releaseOral60 mg
Injection
Solution
Solution; syrupOral
CapsuleOral
Injection, solutionParenteral
CapsuleOral10 mg
Injection, solutionIntravenous; Subcutaneous
CapsuleOral20 mg
CapsuleOral5 mg
SolutionOral
SolutionOral10 mg/ml
Solution, concentrateOral10 mg/ml
SolutionOral1 mg/ml
Injection, solutionIntravenous9 mg/ml
Tablet, extended releaseOral30 MG/15MG
SolutionOral1 g
SolutionOral0.1 g
SolutionIntravenous; Subcutaneous9 mg
Tablet, extended releaseOral10 mg
Tablet, extended releaseOral20 mg
Tablet, extended releaseOral80 mg
SolutionOral
ConcentrateOral20 mg/1mL
SolutionOral5 mg/5mL
Tablet, coatedOral15 mg/1
Tablet, coatedOral30 mg/1
Tablet, coatedOral5 mg/1
TabletOral20 mg
SuppositoryRectal10 mg
TabletOral10 mg
SuppositoryRectal20 mg
TabletOral5 mg
Tablet, extended releaseOral10 MG/5MG
Tablet, extended releaseOral20 MG/10MG
Tablet, extended releaseOral40 MG/20MG
Tablet, extended releaseOral5 MG/2.5MG
Tablet, film coated, extended releaseOral5 mg
Tablet, film coated, extended releaseOral10 mg
Tablet, film coated, extended releaseOral20 mg
Tablet, film coated, extended releaseOral2.5 mg
Tablet, film coated, extended releaseOral
Capsule, extended releaseOral
Capsule, extended releaseOral13.5 mg/1
Capsule, extended releaseOral18 mg/1
Capsule, extended releaseOral27 mg/1
Capsule, extended releaseOral36 mg/1
Capsule, extended releaseOral9 mg/1
Prices
Unit descriptionCostUnit
Oxycodone hcl powder53.64USD g
Roxicodone 5 mg/5ml Solution 500ml Bottle53.0USD bottle
Roxicodone 20 mg/ml Concentrate 30ml Bottle46.99USD bottle
OxyCODONE HCl 20 mg/ml Concentrate 30ml Bottle33.99USD bottle
Oxycontin 60 mg tablet17.08USD tablet
OxyCONTIN 80 mg 12 Hour tablet14.36USD tablet
Oxycontin 20 mg tablet11.87USD tablet
Oxycontin 80 mg tablet11.53USD tablet
OxyCONTIN 60 mg 12 Hour tablet10.57USD tablet
Oxycontin 40 mg tablet9.45USD tablet
OxyCODONE HCl 80 mg 12 Hour tablet8.33USD tablet
OxyCONTIN 40 mg 12 Hour tablet7.68USD tablet
Oxycontin 10 mg tablet6.89USD tablet
Oxycontin 30 mg tablet6.59USD tablet
OxyCONTIN 30 mg 12 Hour tablet5.8USD tablet
Roxicodone 30 mg tablet5.19USD tablet
Oxycontin 80 mg Sustained-Release Tablet4.69USD tablet
OxyCODONE HCl 40 mg 12 Hour tablet4.38USD tablet
OxyCONTIN 20 mg 12 Hour tablet4.27USD tablet
Oxycontin 60 mg Sustained-Release Tablet3.55USD tablet
Oxycontin 15 mg tablet3.22USD tablet
Supeudol 20 mg Suppository2.95USD suppository
Roxicodone 15 mg tablet2.83USD tablet
Oxycodone hcl 10 mg tablet2.82USD tablet
Endocet 10-650 mg tablet2.7USD tablet
Endocet 7.5-325 mg tablet2.54USD tablet
Oxycontin 40 mg Sustained-Release Tablet2.54USD tablet
OxyCONTIN 10 mg 12 Hour tablet2.53USD tablet
Supeudol 10 mg Suppository2.33USD suppository
Roxicodone intensol 20 mg/ml2.3USD ml
Endocet 7.5-500 mg tablet2.22USD tablet
Oxycodone-apap 2.5-325 mg tablet2.05USD tablet
Percodan 4.5-0.38-325 mg tablet1.98USD tablet
Oxycontin 30 mg Sustained-Release Tablet1.96USD tablet
Endocet 10-325 mg tablet1.87USD tablet
Endocet 5-325 tablet1.82USD tablet
Percodan tablet1.62USD tablet
Oxycontin 20 mg Sustained-Release Tablet1.46USD tablet
Dazidox 20 mg tablet1.44USD tablet
Oxycodone hcl 30 mg tablet1.41USD tablet
Oxycontin 15 mg Sustained-Release Tablet1.19USD tablet
Endodan 4.83-325 mg tablet1.18USD tablet
Oxycodone hcl 20 mg tablet1.1USD tablet
Oxycontin 10 mg Sustained-Release Tablet0.98USD tablet
Oxycodone hcl 15 mg tablet0.9USD tablet
Oxycodone hcl 5 mg tablet0.81USD tablet
Dazidox 10 mg tablet0.75USD tablet
Oxy-Ir 20 mg Tablet0.74USD tablet
OxyCODONE HCl 5 mg capsule0.71USD capsule
Oxycontin 5 mg Sustained-Release Tablet0.7USD tablet
Endocet 5-325 mg tablet0.6USD tablet
Roxicodone 5 mg tablet0.56USD tablet
Oxyir 5 mg capsule0.52USD capsule
Oxy-Ir 10 mg Tablet0.43USD tablet
Pms-Oxycodone 20 mg Tablet0.42USD tablet
Supeudol 20 mg Tablet0.42USD tablet
Oxycodone 5 mg tablet0.36USD tablet
Pms-Oxycodone 10 mg Tablet0.24USD tablet
Supeudol 10 mg Tablet0.24USD tablet
Pms-Oxycodone 5 mg Tablet0.14USD tablet
Supeudol 5 mg Tablet0.14USD tablet
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Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5508042No1996-04-162013-04-16US flag
CA2098738No1999-08-172012-11-25Canada flag
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US8309060No2012-11-132023-11-20US flag
US8808741No2014-08-192027-08-24US flag
US9073933No2015-07-072025-03-30US flag
US9060976No2015-06-232022-08-06US flag
US6488963No2002-12-032017-06-24US flag
US7674800No2010-03-092025-03-30US flag
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US8337888No2012-12-252022-08-06US flag
US7776314No2010-08-172025-04-19US flag
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US8372432No2013-02-122029-03-11US flag
US8668929No2014-03-112029-03-11US flag
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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)219http://www.chemspider.com/Chemical-Structure.4447649.html
water solubility166mg/mLhttp://www.chemspider.com/Chemical-Structure.4447649.html
logP0.7https://www.ncbi.nlm.nih.gov/pubmed/8159633
Predicted Properties
PropertyValueSource
Water Solubility5.59 mg/mLALOGPS
logP1.04ALOGPS
logP1.03Chemaxon
logS-1.8ALOGPS
pKa (Strongest Acidic)13.57Chemaxon
pKa (Strongest Basic)8.77Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area59 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity84.04 m3·mol-1Chemaxon
Polarizability32.79 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9924
Blood Brain Barrier+0.9885
Caco-2 permeable+0.7774
P-glycoprotein substrateSubstrate0.8996
P-glycoprotein inhibitor IInhibitor0.539
P-glycoprotein inhibitor IINon-inhibitor0.9122
Renal organic cation transporterNon-inhibitor0.5413
CYP450 2C9 substrateNon-substrate0.822
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.7796
CYP450 1A2 substrateNon-inhibitor0.9327
CYP450 2C9 inhibitorNon-inhibitor0.9431
CYP450 2D6 inhibitorNon-inhibitor0.5131
CYP450 2C19 inhibitorNon-inhibitor0.882
CYP450 3A4 inhibitorNon-inhibitor0.8714
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9691
Ames testNon AMES toxic0.7337
CarcinogenicityNon-carcinogens0.9557
BiodegradationNot ready biodegradable0.9746
Rat acute toxicity3.0638 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9402
hERG inhibition (predictor II)Non-inhibitor0.9279
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0a4i-9061000000-5297e69aa2cc5152068f
Mass Spectrum (Electron Ionization)MSsplash10-014i-6975000000-ecd49efa58246c903e23
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0009000000-d55749fa4d1f47ce2244
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00kb-0095000000-83c78e9e15857145cc78
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0090000000-ad908ecfa38c7efce138
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0006-0390000000-88d302b8770cb7121937
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03fu-0790000000-4af50b834ee854320001
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0019000000-3c9e0fee79279f0b7eb4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0009000000-c10852c5f068ec4b62cb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kb-0096000000-520b0f991c64584a00e1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0009000000-9646653e177e728a059e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0apj-0092000000-eb164162596c0dfa97d2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0079000000-2eb48234d6f13fe68a38
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-175.4179916
predicted
DarkChem Lite v0.1.0
[M-H]-175.5842916
predicted
DarkChem Lite v0.1.0
[M-H]-178.83537
predicted
DeepCCS 1.0 (2019)
[M+H]+175.8588916
predicted
DarkChem Lite v0.1.0
[M+H]+175.8760916
predicted
DarkChem Lite v0.1.0
[M+H]+181.2884
predicted
DeepCCS 1.0 (2019)
[M+Na]+175.4991916
predicted
DarkChem Lite v0.1.0
[M+Na]+175.9775916
predicted
DarkChem Lite v0.1.0
[M+Na]+189.12598
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. Ordonez Gallego A, Gonzalez Baron M, Espinosa Arranz E: Oxycodone: a pharmacological and clinical review. Clin Transl Oncol. 2007 May;9(5):298-307. [Article]
  2. Riley J, Eisenberg E, Muller-Schwefe G, Drewes AM, Arendt-Nielsen L: Oxycodone: a review of its use in the management of pain. Curr Med Res Opin. 2008 Jan;24(1):175-92. [Article]
  3. Dietis N, Guerrini R, Calo G, Salvadori S, Rowbotham DJ, Lambert DG: Simultaneous targeting of multiple opioid receptors: a strategy to improve side-effect profile. Br J Anaesth. 2009 Jul;103(1):38-49. doi: 10.1093/bja/aep129. Epub 2009 May 27. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 Da
References
  1. Ordonez Gallego A, Gonzalez Baron M, Espinosa Arranz E: Oxycodone: a pharmacological and clinical review. Clin Transl Oncol. 2007 May;9(5):298-307. [Article]
  2. Riley J, Eisenberg E, Muller-Schwefe G, Drewes AM, Arendt-Nielsen L: Oxycodone: a review of its use in the management of pain. Curr Med Res Opin. 2008 Jan;24(1):175-92. [Article]
  3. Nielsen CK, Ross FB, Lotfipour S, Saini KS, Edwards SR, Smith MT: Oxycodone and morphine have distinctly different pharmacological profiles: radioligand binding and behavioural studies in two rat models of neuropathic pain. Pain. 2007 Dec 5;132(3):289-300. Epub 2007 Apr 30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Opioid receptor activity
Specific Function
G-protein coupled receptor that functions as receptor for endogenous enkephalins and for a subset of other opioids. Ligand binding causes a conformation change that triggers signaling via guanine n...
Gene Name
OPRD1
Uniprot ID
P41143
Uniprot Name
Delta-type opioid receptor
Molecular Weight
40368.235 Da
References
  1. Ordonez Gallego A, Gonzalez Baron M, Espinosa Arranz E: Oxycodone: a pharmacological and clinical review. Clin Transl Oncol. 2007 May;9(5):298-307. [Article]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Lalovic B, Phillips B, Risler LL, Howald W, Shen DD: Quantitative contribution of CYP2D6 and CYP3A to oxycodone metabolism in human liver and intestinal microsomes. Drug Metab Dispos. 2004 Apr;32(4):447-54. [Article]
  2. DePriest AZ, Puet BL, Holt AC, Roberts A, Cone EJ: Metabolism and Disposition of Prescription Opioids: A Review. Forensic Sci Rev. 2015 Jul;27(2):115-45. [Article]
  3. Stamer UM, Zhang L, Book M, Lehmann LE, Stuber F, Musshoff F: CYP2D6 genotype dependent oxycodone metabolism in postoperative patients. PLoS One. 2013;8(3):e60239. doi: 10.1371/journal.pone.0060239. Epub 2013 Mar 28. [Article]
  4. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Lalovic B, Phillips B, Risler LL, Howald W, Shen DD: Quantitative contribution of CYP2D6 and CYP3A to oxycodone metabolism in human liver and intestinal microsomes. Drug Metab Dispos. 2004 Apr;32(4):447-54. [Article]
  2. DePriest AZ, Puet BL, Holt AC, Roberts A, Cone EJ: Metabolism and Disposition of Prescription Opioids: A Review. Forensic Sci Rev. 2015 Jul;27(2):115-45. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Lalovic B, Phillips B, Risler LL, Howald W, Shen DD: Quantitative contribution of CYP2D6 and CYP3A to oxycodone metabolism in human liver and intestinal microsomes. Drug Metab Dispos. 2004 Apr;32(4):447-54. [Article]
  2. DePriest AZ, Puet BL, Holt AC, Roberts A, Cone EJ: Metabolism and Disposition of Prescription Opioids: A Review. Forensic Sci Rev. 2015 Jul;27(2):115-45. [Article]
  3. Naito T, Takashina Y, Yamamoto K, Tashiro M, Ohnishi K, Kagawa Y, Kawakami J: CYP3A5*3 affects plasma disposition of noroxycodone and dose escalation in cancer patients receiving oxycodone. J Clin Pharmacol. 2011 Nov;51(11):1529-38. doi: 10.1177/0091270010388033. Epub 2011 Jan 5. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Leow KP, Wright AW, Cramond T, Smith MT: Determination of the serum protein binding of oxycodone and morphine using ultrafiltration. Ther Drug Monit. 1993 Oct;15(5):440-7. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:
References
  1. Leow KP, Wright AW, Cramond T, Smith MT: Determination of the serum protein binding of oxycodone and morphine using ultrafiltration. Ther Drug Monit. 1993 Oct;15(5):440-7. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48