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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:40:58 UTC
HMDB IDHMDB0015098
Secondary Accession Numbers
  • HMDB15098
Metabolite Identification
Common NameBromfenac
DescriptionBromfenac, also known as bromfenac sodium or xibrom, belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. Bromfenac is a drug which is used for the treatment of postoperative inflammation in patients who have undergone cataract extraction. Bromfenac ophthalmic solution is a sterile, topical, nonsteroidal anti-inflammatory drug (NSAID) for ophthalmic use. Bromfenac is a moderately basic compound (based on its pKa). In humans, bromfenac is involved in bromfenac action pathway. Bromfenac is a potentially toxic compound. The mechanism of its action is thought to be due to its ability to block prostaglandin synthesis by inhibiting cyclooxygenase 1 and 2. Prostaglandins have been shown in many animal models to be mediators of certain kinds of intraocular inflammation. In studies performed in animal eyes, prostaglandins have been shown to produce disruption of the blood-aqueous humor barrier, vasodilation, increased vascular permeability, leukocytosis, and increased intraocular pressure.
Structure
Data?1582753258
Synonyms
ValueSource
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
XibromHMDB
Sodium bromfenacHMDB
Wyeth brand OF sodium bromfenacHMDB
DuractHMDB
ISV-303MeSH
Chemical FormulaC15H12BrNO3
Average Molecular Weight334.165
Monoisotopic Molecular Weight333.000055902
IUPAC Name2-[2-amino-3-(4-bromobenzoyl)phenyl]acetic acid
Traditional Namebromfenac
CAS Registry Number91714-94-2
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 KeyZBPLOVFIXSTCRZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzophenones
Direct ParentBenzophenones
Alternative Parents
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
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.013 g/LNot Available
LogP3.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity80.26 m³·mol⁻¹ChemAxon
Polarizability29.93 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2942000000-55d5af00fe6fa398beadSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-5391000000-a985cfcf083f34c1b155Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0039000000-8bc362a4cdf601ba45d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0292000000-5eada8c7771779cb0353Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0540-2950000000-5f5aed8a6d28056c567aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-0059000000-17d7c340ec08a0adaba2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001r-1298000000-1d237d5738d709e7bf6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zgi-3892000000-27126ed6eaa7f4fe957eSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00963 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00963 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00963
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54730
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBromfenac
METLIN IDNot Available
PubChem Compound60726
PDB IDNot Available
ChEBI ID240107
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot 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 ]