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Suprofen

July 24, 2017
Common Name

Suprofen Description

Suprofen is only found in individuals that have used or taken this drug. It is an ibuprofen-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic. [PubChem]Suprofen binds to the cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) isoenzymes, preventing the synthesis of prostaglandins and reducing the inflammatory response. Cyclooxygenase catalyses the formation of prostaglandins and thromboxane from arachidonic acid (itself derived from the cellliar phospholipid bilayer by phospholipase A2). Prostaglandins act (among other things) as messenger moleclies in the process of inflammation. The overall reslit is a reduction in pain and inflammation in the eyes and the prevention of pupil constriction during surgery. Normally trauma to the anterior segment of the eye (especially the iris) increases endogenous prostaglandin synthesis which leads to constriction of the iris sphincter. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (+-)-2-(P-(2-Thenoyl)phenyl)propionic acidChEBI 2-(4-(2-Thenoyl)phenyl)propionsaeureChEBI 2-[4-(Thiophene-2-carbonyl)-phenyl]-propionic acidChEBI 4-(2-Thenoyl)hydratropsaeureChEBI alpha-Methyl-4-(2-thienylcarbonyl)benzeneacetic acidChEBI P-2-Thenoylhydratropic acidChEBI PROFENALChEBI SuprofeneChEBI SuprofenumChEBI SUTOPROFENChEBI (+-)-2-(P-(2-Thenoyl)phenyl)propionateGenerator 2-[4-(Thiophene-2-carbonyl)-phenyl]-propionateGenerator a-Methyl-4-(2-thienylcarbonyl)benzeneacetateGenerator a-Methyl-4-(2-thienylcarbonyl)benzeneacetic acidGenerator alpha-Methyl-4-(2-thienylcarbonyl)benzeneacetateGenerator α-methyl-4-(2-thienylcarbonyl)benzeneacetateGenerator α-methyl-4-(2-thienylcarbonyl)benzeneacetic acidGenerator P-2-ThenoylhydratropateGenerator

Chemical Formlia

C14H12O3S Average Molecliar Weight

260.308 Monoisotopic Molecliar Weight

260.05071494 IUPAC Name

2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Traditional Name

suprofen CAS Registry Number

40828-46-4 SMILES

CC(C(O)=O)C1=CC=C(C=C1)C(=O)C1=CC=CS1

InChI Identifier

InChI=1S/C14H12O3S/c1-9(14(16)17)10-4-6-11(7-5-10)13(15)12-3-2-8-18-12/h2-9H,1H3,(H,16,17)

InChI Key

MDKGKXOCJGEUJW-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic oxygen compounds Sub Class

Organooxygen compounds Direct Parent

Aryl-phenylketones Alternative Parents

  • Phenylpropanoic acids
  • Monocyclic monoterpenoids
  • Aromatic monoterpenoids
  • Thiophene carboxylic acids and derivatives
  • Benzoyl derivatives
  • Heteroaromatic compounds
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Aryl-phenylketone
  • 2-phenylpropanoic-acid
  • P-cymene
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Benzoyl
  • Thiophene carboxylic acid or derivatives
  • Benzenoid
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Thiophene
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • monocarboxylic acid (CHEBI:9362 )
  • thiophenes (CHEBI:9362 )
  • aromatic ketone (CHEBI:9362 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Cell signaling
  • Cyclooxygenase Inhibitors
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability

    • Application

  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emlisifiers

    • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point124.3 °CNot Available Boiling PointNot AvailableNot Available Water Solubility4.22e-02 g/LNot Available LogP2.2Not Available

    Predicted Properties

    Property Value Source Water Solubility0.042 mg/mLALOGPS logP3.16ALOGPS logP3.53ChemAxon logS-3.8ALOGPS pKa (Strongest Acidic)4.01ChemAxon pKa (Strongest Basic)-7.8ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area54.37 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity69.41 m3·mol-1ChemAxon Polarizability26.84 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-03di-2790000000-0cf8f983c8b216c951b3View in MoNA 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

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Suprofen PathwaySMP00101Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00870

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00870

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00870 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    5166 KEGG Compound ID

    C07320 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Suprofen NuGOwiki Link

    HMDB15008 Metagene Link

    HMDB15008 METLIN ID

    Not Available PubChem Compound

    5359 PDB ID

    Not Available ChEBI ID

    9362

    Product: Amicarbazone

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

    Enzymes

    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
    Gene Name:
    UGT2B7
    Uniprot ID:
    P16662
    Molecular weight:
    60720.15
    References
    1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
    Gene Name:
    UGT1A1
    Uniprot ID:
    P22309
    Molecular weight:
    59590.91
    References
    1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
    General function:
    Involved in peroxidase activity
    Specific function:
    Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
    Gene Name:
    PTGS2
    Uniprot ID:
    P35354
    Molecular weight:
    68995.625
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
    3. Llorens O, Perez JJ, Palomer A, Mauleon D: Differential binding mode of diverse cyclooxygenase inhibitors. J Mol Graph Model. 2002 Mar;20(5):359-71. [PubMed:11885959 ]
    General function:
    Involved in peroxidase activity
    Specific function:
    May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
    Gene Name:
    PTGS1
    Uniprot ID:
    P23219
    Molecular weight:
    68685.82
    References
    1. Loll PJ, Picot D, Ekabo O, Garavito RM: Synthesis and use of iodinated nonsteroidal antiinflammatory drug analogs as crystallographic probes of the prostaglandin H2 synthase cyclooxygenase active site. Biochemistry. 1996 Jun 11;35(23):7330-40. [PubMed:8652509 ]
    2. Bender A, Scheiber J, Glick M, Davies JW, Azzaoui K, Hamon J, Urban L, Whitebread S, Jenkins JL: Analysis of pharmacology data and the prediction of adverse drug reactions and off-target effects from chemical structure. ChemMedChem. 2007 Jun;2(6):861-73. [PubMed:17477341 ]
    3. Llorens O, Perez JJ, Palomer A, Mauleon D: Differential binding mode of diverse cyclooxygenase inhibitors. J Mol Graph Model. 2002 Mar;20(5):359-71. [PubMed:11885959 ]
    4. 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 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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
    Gene Name:
    CYP2C9
    Uniprot ID:
    P11712
    Molecular weight:
    55627.365
    References
    1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
    2. 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 ]

    PMID: 23146662

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