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Bromfenac

July 24, 2017
Common Name

Bromfenac Description

Bromfenac is a nonsteroidal anti-inflammatory drug (NSAID) for ophthalmic use. Ophthalmic NSAIDs are becoming a cornerstone for the management of ocliar pain and inflammation. Their well-characterized anti-inflammatory activity, analgesic property, and established safety record have also made NSAIDs an important tool to optimize surgical outcomes. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 2-amino-3-(4-Bromobenzoyl)benzeneacetic acidChEBI [2-amino-3-(4-bromo-Benzoyl)-phenyl]-acetic acidChEBI BromfenacoChEBI BromfenacumChEBI 2-amino-3-(4-Bromobenzoyl)benzeneacetateGenerator [2-amino-3-(4-bromo-Benzoyl)-phenyl]-acetateGenerator Bromfenac sodiumHMDB XibromMeSH Sodium bromfenacMeSH Wyeth brand OF sodium bromfenacMeSH DuractMeSH

Chemical Formlia

C15H12BrNO3 Average Molecliar Weight

334.165 Monoisotopic Molecliar Weight

333.000055902 IUPAC Name

2-[2-amino-3-(4-bromobenzoyl)phenyl]acetic acid Traditional Name

bromfenac CAS Registry Number

91714-94-2 SMILES

NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(Br)C=C1

InChI Identifier

InChI=1S/C15H12BrNO3/c16-11-6-4-9(5-7-11)15(20)12-3-1-2-10(14(12)17)8-13(18)19/h1-7H,8,17H2,(H,18,19)

InChI Key

ZBPLOVFIXSTCRZ-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. Kingdom

Organic compounds Super Class

Benzenoids Class

Benzene and substituted derivatives Sub Class

Benzophenones Direct Parent

Benzophenones Alternative Parents

  • Diphenylmethanes
  • Aryl-phenylketones
  • Benzoyl derivatives
  • Aniline and substituted anilines
  • Bromobenzenes
  • Aryl bromides
  • Vinylogous amides
  • Amino acids
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Primary amines
  • Organopnictogen compounds
  • Organobromides
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Benzophenone
  • Diphenylmethane
  • Aryl-phenylketone
  • Benzoyl
  • Aryl ketone
  • Aniline or substituted anilines
  • Bromobenzene
  • Halobenzene
  • Aryl bromide
  • Aryl halide
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organopnictogen compound
  • Organobromide
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organic oxide
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • organobromine compound (CHEBI:240107 )
  • benzophenones (CHEBI:240107 )
  • substituted aniline (CHEBI:240107 )
  • aromatic amino acid (CHEBI:240107 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Analgesics

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility1.26e-02 g/LNot Available LogP3.4Not Available

    Predicted Properties

    Property Value Source Water Solubility0.013 mg/mLALOGPS logP3ALOGPS logP3.66ChemAxon logS-4.4ALOGPS pKa (Strongest Acidic)3.81ChemAxon pKa (Strongest Basic)1.59ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area80.39 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity80.26 m3·mol-1ChemAxon Polarizability29.93 Å3ChemAxon Number of Rings2ChemAxon 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

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Bromfenac PathwaySMP00102Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00963

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00963

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00963 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

    54730 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB15098 Metagene Link

    HMDB15098 METLIN ID

    Not Available PubChem Compound

    60726 PDB ID

    Not Available ChEBI ID

    240107

    Product: Berberine (chloride hydrate)

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

    Enzymes

    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. Waterbury LD, Silliman D, Jolas T: Comparison of cyclooxygenase inhibitory activity and ocular anti-inflammatory effects of ketorolac tromethamine and bromfenac sodium. Curr Med Res Opin. 2006 Jun;22(6):1133-40. [PubMed:16846546 ]
    2. Sanchez-Matienzo D, Arana A, Castellsague J, Perez-Gutthann S: Hepatic disorders in patients treated with COX-2 selective inhibitors or nonselective NSAIDs: a case/noncase analysis of spontaneous reports. Clin Ther. 2006 Aug;28(8):1123-32. [PubMed:16982289 ]
    3. Chitturi S, George J: Hepatotoxicity of commonly used drugs: nonsteroidal anti-inflammatory drugs, antihypertensives, antidiabetic agents, anticonvulsants, lipid-lowering agents, psychotropic drugs. Semin Liver Dis. 2002;22(2):169-83. [PubMed:12016548 ]
    4. Cho H, Wolf KJ, Wolf EJ: Management of ocular inflammation and pain following cataract surgery: focus on bromfenac ophthalmic solution. Clin Ophthalmol. 2009;3:199-210. Epub 2009 Jun 2. [PubMed:19668566 ]
    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. Waterbury LD, Silliman D, Jolas T: Comparison of cyclooxygenase inhibitory activity and ocular anti-inflammatory effects of ketorolac tromethamine and bromfenac sodium. Curr Med Res Opin. 2006 Jun;22(6):1133-40. [PubMed:16846546 ]
    2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

    PMID: 27738012

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