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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2019-01-11 19:33:59 UTC
HMDB IDHMDB0014640
Secondary Accession Numbers
  • HMDB14640
Metabolite Identification
Common NameOxycodone
DescriptionOxycodone is only found in individuals that have used or taken this drug. It is a semisynthetic derivative of codeine that acts as a narcotic analgesic more potent and addicting than codeine. [PubChem]Oxycodone acts as a weak agonist at mu, kappa, and delta opioid receptors within the central nervous system (CNS). Oxycodone primarily affects mu-type opioid receptors, which are coupled with G-protein receptors and function as modulators, both positive and negative, of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine, and noradrenaline is inhibited. Opioids such as oxycodone also inhibit the release of vasopressin, somatostatin, insulin, and glucagon. Opioids close N-type voltage-operated calcium channels (kappa-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (mu and delta receptor agonist). This results in hyperpolarization and reduced neuronal excitability.
Structure
Data?1547235239
Synonyms
ValueSource
(-)-14-HydroxydihydrocodeinoneChEBI
4,5-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-oneChEBI
4,5alpha-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-oneChEBI
dihydro-14-HydroxycodeinoneChEBI
DihydrohydroxycodeinoneChEBI
DihydroxycodeinoneChEBI
OxicodonaChEBI
OxycodonumChEBI
4,5a-Epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-oneGenerator
4,5α-epoxy-14-hydroxy-3-methoxy-17-methylmorphinan-6-oneGenerator
DihydrohydroxycondeinoneHMDB
DihydroneHMDB
PTI-821HMDB
DinarkonMeSH
OxiconumMeSH
OxyconeMeSH
OxycontinMeSH
TheocodinMeSH
EucodalMeSH
OxycodeinonMeSH
Oxycodone hydrochlorideMeSH
PancodineMeSH
Purdue frederick brand OF oxycodoneMeSH
Chemical FormulaC18H21NO4
Average Molecular Weight315.3636
Monoisotopic Molecular Weight315.147058165
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
Traditional 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
CAS Registry Number76-42-6
SMILES
[H][C@@]12OC3=C(OC)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1(O)CCC2=O
InChI Identifier
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
InChI KeyBRUQQQPBMZOVGD-XFKAJCMBSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassNot Available
Direct ParentPhenanthrenes and derivatives
Alternative Parents
Substituents
  • Phenanthrene
  • Isoquinolone
  • Tetralin
  • Coumaran
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Cyclic alcohol
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • 1,2-aminoalcohol
  • Ketone
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Alcohol
  • Organonitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point218 - 220 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.59 g/LNot Available
LogP0.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.59 g/LALOGPS
logP1.04ALOGPS
logP1.03ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)13.56ChemAxon
pKa (Strongest Basic)8.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity84.04 m³·mol⁻¹ChemAxon
Polarizability32.79 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9061000000-5297e69aa2cc5152068fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9538000000-1b9bf2a9c0682b6738c4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0009000000-d55749fa4d1f47ce2244JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00kb-0095000000-83c78e9e15857145cc78JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0090000000-ad908ecfa38c7efce138JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0390000000-88d302b8770cb7121937JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03fu-0790000000-4af50b834ee854320001JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0095000000-187a15135033fe090084JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1091000000-36b41da08ca2b913a212JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-5090000000-a251627d2dc7a2e0750cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0029000000-9ffd2b473cfe2ec06b32JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-1096000000-a01cf940a0da1fca0ffdJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-2090000000-da3286e89dfed1ee6a32JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-014i-6975000000-ecd49efa58246c903e23JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00497 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00497 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00497
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4447649
KEGG Compound IDC08018
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOxycodone
METLIN IDNot Available
PubChem Compound5284603
PDB IDNot Available
ChEBI ID7852
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General 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. [PubMed:17525040 ]
  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. [PubMed:18039433 ]

Enzymes

General function:
Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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. [PubMed:15039299 ]
General function:
Involved in monooxygenase 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 antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. 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. [PubMed:15039299 ]
General function:
Involved in monooxygenase 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular weight:
57525.03
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins
Gene Name:
OPRD1
Uniprot ID:
P41143
Molecular weight:
40412.3
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. [PubMed:17525040 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
Gene Name:
OPRM1
Uniprot ID:
P35372
Molecular weight:
44778.9
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. [PubMed:17525040 ]
  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. [PubMed:18039433 ]
  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. [PubMed:19474215 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions
Gene Name:
OPRK1
Uniprot ID:
P41145
Molecular weight:
42644.7
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. [PubMed:17525040 ]
  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. [PubMed:18039433 ]
  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. [PubMed:17467904 ]