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Oxymorphone

July 24, 2017
Common Name

Oxymorphone Description

An opioid analgesic with actions and uses similar to those of morphine, apart from an absence of cough suppressant activity. It is used in the treatment of moderate to severe pain, including pain in obstetrics. It may also be used as an adjunct to anesthesia. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1092) Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source NumorphanChEMBL OpanaChEMBL 14-HydroxydihydromorphinoneHMDB DihydrohydroxymorphinoneHMDB DihydroxymorphinoneHMDB EN3202HMDB OximorphonumHMDB OxymorphineHMDB Bristol-myers squibb brand OF oxymorphone hydrochlorideMeSH Oxymorphone HCLMeSH endo Brand OF oxymorphone hydrochlorideMeSH Oxymorphone hydrochlorideMeSH endo Brand OF oxymorphine HCLMeSH

Chemical Formlia

C17H19NO4 Average Molecliar Weight

301.3371 Monoisotopic Molecliar Weight

301.131408101 IUPAC Name

(1S,5R,13R,17S)-10,17-dihydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one Traditional Name

oxymorphone CAS Registry Number

76-41-5 SMILES

[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1(O)CCC2=O

InChI Identifier

InChI=1S/C17H19NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-3,12,15,19,21H,4-8H2,1H3/t12-,15+,16+,17-/m1/s1

InChI Key

UQCNKQCJZOAFTQ-ISWURRPUSA-N Chemical Taxonomy 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
  • 1-hydroxy-2-unsubstituted benzenoids
  • Alkyl aryl ethers
  • Aralkylamines
  • Piperidines
  • Tertiary alcohols
  • Trialkylamines
  • 1,2-aminoalcohols
  • Ketones
  • Cyclic alcohols and derivatives
  • Oxacyclic compounds
  • Azacyclic compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Organopnictogen compounds

    • Substituents

  • Phenanthrene
  • Isoquinolone
  • Tetralin
  • Coumaran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Cyclic alcohol
  • Tertiary alcohol
  • 1,2-aminoalcohol
  • Ketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ether
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • morphinane alkaloid (CHEBI:7865 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

  • Drug metabolite

    • Biofunction

  • Adjuvants
  • Adjuvants, Anesthesia
  • Analgesics
  • Analgesics, Opioid
  • Narcotics
  • Opiate Agonists
  • Waste products

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point248 – 249 °CNot Available Boiling PointNot AvailableNot Available Water Solubility2.56e+01 g/LNot Available LogP0Not Available

    Predicted Properties

    Property Value Source Water Solubility25.6 mg/mLALOGPS logP1.26ALOGPS logP0.78ChemAxon logS-1.1ALOGPS pKa (Strongest Acidic)7.34ChemAxon pKa (Strongest Basic)10.93ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area70 Å2ChemAxon Rotatable Bond Count0ChemAxon Refractivity79.56 m3·mol-1ChemAxon Polarizability30.77 Å3ChemAxon Number of Rings5ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available MS

    Mass Spectrum (Electron Ionization)splash10-0udl-7932000000-89141254d526ca629dacView in MoNA

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Oxymorphone PathwaySMP00412Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01192

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01192

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-0.3 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-0.2 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01192 DrugBank Metabolite ID

    DBMET00321 Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    4447650 KEGG Compound ID

    C08019 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Oxymorphone NuGOwiki Link

    HMDB15323 Metagene Link

    HMDB15323 METLIN ID

    Not Available PubChem Compound

    5284604 PDB ID

    Not Available ChEBI ID

    194484

    Product: Pulsatilla saponin D

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    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. Gronlund J, Saari TI, Hagelberg NM, Neuvonen PJ, Olkkola KT, Laine K: Exposure to oral oxycodone is increased by concomitant inhibition of CYP2D6 and 3A4 pathways, but not by inhibition of CYP2D6 alone. Br J Clin Pharmacol. 2010 Jul;70(1):78-87. doi: 10.1111/j.1365-2125.2010.03653.x. [PubMed:20642550 ]
    2. Samer CF, Daali Y, Wagner M, Hopfgartner G, Eap CB, Rebsamen MC, Rossier MF, Hochstrasser D, Dayer P, Desmeules JA: The effects of CYP2D6 and CYP3A activities on the pharmacokinetics of immediate release oxycodone. Br J Pharmacol. 2010 Jun;160(4):907-18. doi: 10.1111/j.1476-5381.2010.00673.x. [PubMed:20590587 ]
    3. Lalovic B, Kharasch E, Hoffer C, Risler L, Liu-Chen LY, Shen DD: Pharmacokinetics and pharmacodynamics of oral oxycodone in healthy human subjects: role of circulating active metabolites. Clin Pharmacol Ther. 2006 May;79(5):461-79. [PubMed:16678548 ]
    4. Adams M, Pieniaszek HJ Jr, Gammaitoni AR, Ahdieh H: Oxymorphone extended release does not affect CYP2C9 or CYP3A4 metabolic pathways. J Clin Pharmacol. 2005 Mar;45(3):337-45. [PubMed:15703368 ]
    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. Gronlund J, Saari TI, Hagelberg NM, Neuvonen PJ, Olkkola KT, Laine K: Exposure to oral oxycodone is increased by concomitant inhibition of CYP2D6 and 3A4 pathways, but not by inhibition of CYP2D6 alone. Br J Clin Pharmacol. 2010 Jul;70(1):78-87. doi: 10.1111/j.1365-2125.2010.03653.x. [PubMed:20642550 ]
    2. Samer CF, Daali Y, Wagner M, Hopfgartner G, Eap CB, Rebsamen MC, Rossier MF, Hochstrasser D, Dayer P, Desmeules JA: The effects of CYP2D6 and CYP3A activities on the pharmacokinetics of immediate release oxycodone. Br J Pharmacol. 2010 Jun;160(4):907-18. doi: 10.1111/j.1476-5381.2010.00673.x. [PubMed:20590587 ]
    3. Lalovic B, Kharasch E, Hoffer C, Risler L, Liu-Chen LY, Shen DD: Pharmacokinetics and pharmacodynamics of oral oxycodone in healthy human subjects: role of circulating active metabolites. Clin Pharmacol Ther. 2006 May;79(5):461-79. [PubMed:16678548 ]
    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. Chamberlin KW, Cottle M, Neville R, Tan J: Oral oxymorphone for pain management. Ann Pharmacother. 2007 Jul;41(7):1144-52. Epub 2007 Jun 26. [PubMed:17595308 ]
    2. Ananthan S, Khare NK, Saini SK, Seitz LE, Bartlett JL, Davis P, Dersch CM, Porreca F, Rothman RB, Bilsky EJ: Identification of opioid ligands possessing mixed micro agonist/delta antagonist activity among pyridomorphinans derived from naloxone, oxymorphone, and hydromorphone [correction of hydropmorphone]. J Med Chem. 2004 Mar 11;47(6):1400-12. [PubMed:14998329 ]
    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. Spetea M, Nevin ST, Hosztafi S, Ronai AZ, Toth G, Borsodi A: Affinity profiles of novel delta-receptor selective benzofuran derivatives of non-peptide opioids. Neurochem Res. 1998 Sep;23(9):1211-6. [PubMed:9712193 ]
    2. Lemberg KK, Kontinen VK, Siiskonen AO, Viljakka KM, Yli-Kauhaluoma JT, Korpi ER, Kalso EA: Antinociception by spinal and systemic oxycodone: why does the route make a difference? In vitro and in vivo studies in rats. Anesthesiology. 2006 Oct;105(4):801-12. [PubMed:17006080 ]
    3. Chamberlin KW, Cottle M, Neville R, Tan J: Oral oxymorphone for pain management. Ann Pharmacother. 2007 Jul;41(7):1144-52. Epub 2007 Jun 26. [PubMed:17595308 ]
    4. Halimi G, Devaux C, Clot-Faybesse O, Sampol J, Legof L, Rochat H, Guieu R: Modulation of adenosine concentration by opioid receptor agonists in rat striatum. Eur J Pharmacol. 2000 Jun 16;398(2):217-24. [PubMed:10854833 ]
    5. Gardell LR, King T, Ossipov MH, Rice KC, Lai J, Vanderah TW, Porreca F: Opioid receptor-mediated hyperalgesia and antinociceptive tolerance induced by sustained opiate delivery. Neurosci Lett. 2006 Mar 20;396(1):44-9. Epub 2005 Dec 15. [PubMed:16343768 ]
    6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

    PMID: 17994112

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