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Identification
NameBromfenac
Accession NumberDB00963  (APRD00831)
TypeSmall Molecule
GroupsApproved
Description

Bromfenac is a nonsteroidal anti-inflammatory drug (NSAID) for ophthalmic use. Ophthalmic NSAIDs are becoming a cornerstone for the management of ocular 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
Thumb
Synonyms
[2-Amino-3-(4-bromo-benzoyl)-phenyl]-acetic acid
2-amino-3-(4-Bromobenzoyl)benzeneacetic acid
Bromfenaco
Bromfenacum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bromdaysolution/ drops.9 mg/mLophthalmicIsta Pharmaceuticals, Inc2010-09-20Not applicableUs
Bromdaysolution/ drops.9 mg/mLophthalmicPhysicians Total Care, Inc.2011-09-30Not applicableUs
Bromdaysolution/ drops.9 mg/mLophthalmicUnit Dose Services2010-09-20Not applicableUs
Prolensasolution/ drops.7 mg/mLophthalmicBausch & Lomb Incorporated2013-04-08Not applicableUs
Prolensasolution0.07 %ophthalmicBausch & Lomb Inc2015-09-25Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bromfenacsolution/ drops.9 mg/mLophthalmicMylan Pharmaceuticals, Inc.2011-05-11Not applicableUs
Bromfenacsolution/ drops.9 mg/mLophthalmicApotex Corp2014-06-19Not applicableUs
Bromfenacsolution/ drops1.035 mg/mLophthalmicPhysicians Total Care, Inc.2012-04-13Not applicableUs
Bromfenacsolution/ drops1.035 mg/mLophthalmicHi Tech Pharmacal Co., Inc.2014-01-22Not applicableUs
Bromfenacsolution/ drops.9 mg/mLophthalmicMylan Pharmaceuticals, Inc.2011-05-11Not applicableUs
Bromfenacsolution/ drops.9 mg/mLophthalmicMylan Pharmaceuticals, Inc.2011-05-11Not applicableUs
Bromfenac Ophthalmic Solution, 0.09%solution/ drops1.035 mg/mLophthalmicApotex Corp.2014-06-23Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DuractWyeth-Ayerst
XibromISTA Pharmaceuticals
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Bromfenac sodium
120638-55-3
Thumb
  • InChI Key: PPOSVVJOVKVBPW-UHFFFAOYSA-L
  • Monoisotopic Mass: 763.995695148
  • Average Mass: 766.339
DBSALT000356
Categories
UNII864P0921DW
CAS number91714-94-2
WeightAverage: 334.165
Monoisotopic: 333.000055902
Chemical FormulaC15H12BrNO3
InChI KeyInChIKey=ZBPLOVFIXSTCRZ-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-[2-amino-3-(4-bromobenzoyl)phenyl]acetic acid
SMILES
NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(Br)C=C1
Taxonomy
DescriptionThis compound 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
  • Phenylacetate
  • Acetophenone
  • Substituted aniline
  • Aryl ketone
  • Benzoyl
  • Halobenzene
  • Bromobenzene
  • Aniline
  • Primary aromatic amine
  • Aryl halide
  • Aryl bromide
  • Vinylogous amide
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organobromide
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of postoperative inflammation in patients who have undergone cataract extraction.
PharmacodynamicsBromfenac ophthalmic solution is a sterile, topical, nonsteroidal anti-inflammatory drug (NSAID) for ophthalmic use.
Mechanism of actionThe 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.
Related Articles
AbsorptionThe plasma concentration of bromfenac following ocular administration in humans is unknown.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Bromfenac Action PathwayDrug actionSMP00102
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9133
Blood Brain Barrier+0.8403
Caco-2 permeable+0.5999
P-glycoprotein substrateNon-substrate0.7803
P-glycoprotein inhibitor INon-inhibitor0.663
P-glycoprotein inhibitor IINon-inhibitor0.8983
Renal organic cation transporterNon-inhibitor0.921
CYP450 2C9 substrateNon-substrate0.8624
CYP450 2D6 substrateNon-substrate0.898
CYP450 3A4 substrateNon-substrate0.7483
CYP450 1A2 substrateNon-inhibitor0.7326
CYP450 2C9 inhibitorNon-inhibitor0.6515
CYP450 2D6 inhibitorNon-inhibitor0.9003
CYP450 2C19 inhibitorNon-inhibitor0.8688
CYP450 3A4 inhibitorNon-inhibitor0.8927
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7996
Ames testNon AMES toxic0.88
CarcinogenicityNon-carcinogens0.7301
BiodegradationNot ready biodegradable0.9618
Rat acute toxicity2.5564 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9747
hERG inhibition (predictor II)Non-inhibitor0.8313
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Ista pharmaceuticals
Packagers
Dosage forms
FormRouteStrength
Solution/ dropsophthalmic.9 mg/mL
Solution/ dropsophthalmic1.035 mg/mL
Solutionophthalmic0.07 %
Solution/ dropsophthalmic.7 mg/mL
Prices
Unit descriptionCostUnit
Xibrom 0.09% Solution 5ml Bottle289.59USD bottle
Xibrom 0.09% Solution 2.5ml Bottle148.56USD bottle
Xibrom 0.09% eye drops68.57USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8129431 No2005-09-112025-09-11Us
US8669290 No2004-01-162024-01-16Us
US8754131 No2004-01-162024-01-16Us
US8778999 No2009-09-032029-09-03Us
US8871813 No2004-01-162024-01-16Us
US8927606 No2004-01-162024-01-16Us
US9144609 No2004-01-162024-01-16Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP3.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0126 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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Shirou Sawa, “Aqueous solution preparation containing aminoglycoside antibiotic and bromfenac.” U.S. Patent US20070082857, issued April 12, 2007.

US20070082857
General ReferencesNot Available
External Links
ATC CodesS01BC11
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (41.5 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
PrednisoloneThe risk or severity of adverse effects can be increased when Bromfenac is combined with Prednisolone.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular Weight:
68995.625 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular Weight:
68995.625 Da
References
  1. 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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 24, 2016 02:49