Identification

Name
Bromfenac
Accession Number
DB00963  (APRD00831)
Type
Small Molecule
Groups
Approved
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 IDs
ISV-303
Product Ingredients
IngredientUNIICASInChI Key
Bromfenac sodium8ECV571Y37120638-55-3PPOSVVJOVKVBPW-UHFFFAOYSA-L
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BromdaySolution / drops0.9 mg/1mLOphthalmicUnit Dose Services2010-09-20Not applicableUs
BromdaySolution / drops0.9 mg/1mLOphthalmicIsta Pharmaceuticals2010-09-202017-12-29Us
BromdaySolution / drops0.9 mg/1mLOphthalmicBauch & Lomb Incorporated2010-09-202014-10-31Us
BromdaySolution / drops0.9 mg/1mLOphthalmicPhysicians Total Care, Inc.2011-09-30Not applicableUs
BromSite 0.075%Solution / drops0.76 mg/1mLOphthalmicSun Pharmaceutical Industries Limited2016-05-01Not applicableUs
ProlensaSolution0.07 %OphthalmicBausch & Lomb Inc2015-09-25Not applicableCanada
ProlensaSolution / drops0.7 mg/1mLOphthalmicBauch & Lomb Incorporated2013-04-05Not applicableUs
XibromSolution0.9 mg/1mLOphthalmicIsta Pharmaceuticals, Inc2005-01-052012-08-31Us
YelloxSolution / drops0.9 mg/mlOphthalmicPharma Swiss Ceska Republika S.R.O2011-05-18Not applicableEu
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BromfenacSolution / drops0.9 mg/1mLOphthalmicMylan Pharmaceuticals2011-05-112016-04-30Us
BromfenacSolution / drops1.035 mg/1mLOphthalmicPhysicians Total Care, Inc.2012-04-13Not applicableUs
BromfenacSolution / drops0.9 mg/1mLOphthalmicMylan Pharmaceuticals2011-05-112016-08-31Us
BromfenacSolution / drops1.035 mg/1mLOphthalmicHi Tech Pharmacal Co., Inc.2014-01-22Not applicableUs
BromfenacSolution / drops0.9 mg/1mLOphthalmicMylan Pharmaceuticals2011-05-112016-04-30Us
BromfenacSolution / drops0.9 mg/1mLOphthalmicBauch & Lomb Incorporated2013-10-162015-09-30Us
BromfenacSolution / drops0.9 mg/1mLOphthalmicApotex Corporation2014-06-192017-07-31Us
Bromfenac Ophthalmic Solution, 0.09%Solution / drops1.035 mg/1mLOphthalmicApotex Corporation2014-06-232017-07-31Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Pred Phos - BromBromfenac sodium (0.75 mg/1mL) + Prednisolone sodium phosphate (10 mg/1mL)Solution / dropsOphthalmicImprimis Njof, Llc2018-07-02Not applicableUs
Pred Phos-Gati-BromBromfenac (0.75 mg/1mL) + Gatifloxacin sesquihydrate (5 mg/1mL) + Prednisolone sodium phosphate (10 mg/1mL)Solution / dropsOphthalmicImprimis Njof, Llc2018-07-02Not applicableUs
Pred-BromBromfenac sodium (0.75 mg/1mL) + Prednisolone acetate (10 mg/1mL)Suspension / dropsOphthalmicImprimis Njof, Llc2018-01-05Not applicableUs
Pred-BromBromfenac (0.75 mg/1mL) + Prednisolone acetate (10 mg/1mL)Suspension / dropsOphthalmicImprimisRx NJ2018-02-01Not applicableUs
Pred-Gati-BromBromfenac sodium (0.75 mg/1mL) + Gatifloxacin sesquihydrate (5 mg/1mL) + Prednisolone acetate (10 mg/1mL)Suspension / dropsOphthalmicImprimis Njof, Llc2018-01-12Not applicableUs
Pred-Gati-BromBromfenac (0.75 mg/1mL) + Gatifloxacin hemihydrate (5 mg/1mL) + Prednisolone acetate (10 mg/1mL)Suspension / dropsOphthalmicImprimisRx NJ2018-01-01Not applicableUs
Pred-Gati-BromBromfenac (0.75 mg/1mL) + Gatifloxacin sesquihydrate (5 mg/1mL) + Prednisolone acetate (10 mg/1mL)Suspension / dropsOphthalmicImprims Njof, Llc2018-01-05Not applicableUs
International/Other Brands
Duract (Wyeth-Ayerst) / Xibrom (ISTA Pharmaceuticals)
Categories
UNII
864P0921DW
CAS number
91714-94-2
Weight
Average: 334.165
Monoisotopic: 333.000055902
Chemical Formula
C15H12BrNO3
InChI Key
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

Pharmacology

Indication

For the treatment of postoperative inflammation in patients who have undergone cataract extraction.

Associated Conditions
Pharmacodynamics

Bromfenac ophthalmic solution is a sterile, topical, nonsteroidal anti-inflammatory drug (NSAID) for ophthalmic use.

Mechanism of action

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.

TargetActionsOrganism
AProstaglandin G/H synthase 2
inhibitor
Human
UProstaglandin G/H synthase 1
inhibitor
Human
Absorption

The plasma concentration of bromfenac following ocular administration in humans is unknown.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Bromfenac Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of gastrointestinal bleeding can be increased when Bromfenac is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of gastrointestinal bleeding can be increased when Bromfenac is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of gastrointestinal bleeding can be increased when Bromfenac is combined with 4-hydroxycoumarin.
AbacavirBromfenac may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Bromfenac is combined with Abciximab.
AcarboseBromfenac may decrease the excretion rate of Acarbose which could result in a higher serum level.
AcebutololBromfenac may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Bromfenac is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Bromfenac is combined with Acemetacin.
AcenocoumarolThe risk or severity of gastrointestinal bleeding can be increased when Bromfenac is combined with Acenocoumarol.
Food Interactions
Not Available

References

Synthesis Reference

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

US20070082857
General References
Not Available
External Links
Human Metabolome Database
HMDB0015098
PubChem Compound
60726
PubChem Substance
46508121
ChemSpider
54730
ChEBI
240107
ChEMBL
CHEMBL1077
Therapeutic Targets Database
DAP000732
PharmGKB
PA448670
HET
27R
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Bromfenac
ATC Codes
S01BC11 — Bromfenac
AHFS Codes
  • 52:08.20 — Nonsteroidal Anti-inflammatory Agents
PDB Entries
4mjq
FDA label
Download (41.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Unknown StatusTreatmentDiabetic Macular Edema (DME)1
1, 2CompletedTreatmentCataracts / Ocular inflammatory conditions / Pain1
2CompletedTreatmentCataract operation1
2CompletedTreatmentCataracts1
2WithdrawnNot AvailableCystoid Macular Edema1
3CompletedPreventionCataracts / Cystoid Macular Edema / Diabetes Mellitus (DM)1
3CompletedTreatmentCataracts2
3CompletedTreatmentCataracts / Inflammatory Reaction / Pain1
3CompletedTreatmentCataracts / Postoperative Complications1
3CompletedTreatmentCataracts / Ocular inflammatory conditions2
3CompletedTreatmentConjunctivitis, Seasonal Allergic1
3CompletedTreatmentInflammatory Reaction / Pain2
3CompletedTreatmentOcular inflammatory conditions1
4Active Not RecruitingTreatmentInflammation Eye1
4CompletedNot AvailableMyopia1
4CompletedPreventionCystoid Macular Edema / Retinal Thickening1
4CompletedTreatmentAcute Pseudophakic Cystoid Macular Edema1
4CompletedTreatmentCataracts5
4CompletedTreatmentCataracts / Pseudoexfoliation Syndrome1
4CompletedTreatmentDiabetic Macular Edema (DME)1
4CompletedTreatmentDry Eye Syndrome (DES) / Ocular Comfort1
4CompletedTreatmentInflammatory Reaction / Pseudophakia1
4CompletedTreatmentIntraocular Pressure1
4CompletedTreatmentPost Operative Anterior Chamber Inflammation (Flare)1
4RecruitingPreventionCataracts1
4RecruitingTreatmentOcular inflammatory conditions / Ocular Pain / Post-surgical Inflammation / Pterygium1
Not AvailableCompletedTreatmentCataracts1
Not AvailableRecruitingTreatmentCataracts / Inflammatory Reaction / Retinal Edema1

Pharmacoeconomics

Manufacturers
  • Ista pharmaceuticals
Packagers
  • Bausch & Lomb Inc.
  • ISTA Pharmaceuticals
Dosage forms
FormRouteStrength
Solution / dropsOphthalmic0.9 mg/1mL
Solution / dropsOphthalmic1.035 mg/1mL
Solution / dropsOphthalmic0.76 mg/1mL
Solution / dropsOphthalmic
Suspension / dropsOphthalmic
SolutionOphthalmic0.07 %
Solution / dropsOphthalmic0.7 mg/1mL
SolutionOphthalmic0.9 mg/1mL
Solution / dropsOphthalmic0.9 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)
US8927606No2004-01-162024-01-16Us
US8871813No2004-01-162024-01-16Us
US8129431No2005-09-112025-09-11Us
US9144609No2004-01-162024-01-16Us
US8669290No2004-01-162024-01-16Us
US8754131No2004-01-162024-01-16Us
US8778999No2009-09-032029-09-03Us
US9517220No2013-11-112033-11-11Us
US9561277No2004-01-162024-01-16Us

Properties

State
Solid
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

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
show 5 more
Substituents
Benzophenone / Diphenylmethane / Aryl-phenylketone / Benzoyl / Aryl ketone / Aniline or substituted anilines / Bromobenzene / Halobenzene / Aryl bromide / Aryl halide
show 20 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organobromine compound, benzophenones, substituted aniline, aromatic amino acid (CHEBI:240107)

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...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
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 gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
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...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
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]

Drug created on June 13, 2005 07:24 / Updated on October 16, 2018 08:32