Bromfenac

Identification

Summary

Bromfenac is an NSAID used to treat postoperative pain and inflammation of the eye.

Brand Names
Bromday, Bromsite, Prolensa, Xibrom
Generic Name
Bromfenac
DrugBank Accession Number
DB00963
Background

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 for optimizing surgical outcomes. Non-ophthalmic formulations of bromfenac were withdrawn in the US in 1998 due to cases of severe liver toxicity.2,1

Type
Small Molecule
Groups
Approved, Withdrawn
Structure
Weight
Average: 334.165
Monoisotopic: 333.000055902
Chemical Formula
C15H12BrNO3
Synonyms
  • [2-Amino-3-(4-bromo-benzoyl)-phenyl]-acetic acid
  • 2-amino-3-(4-bromobenzoyl)benzeneacetic acid
  • Bromfenac
  • Bromfenaco
  • Bromfenacum
External IDs
  • ISV-303

Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofEye inflammation••••••••••••
Management ofOcular pain••••••••••••
Contraindications & Blackbox Warnings
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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
Humans
UProstaglandin G/H synthase 1
inhibitor
Humans
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

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Bromfenac Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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.
Acetylsalicylic acidThe therapeutic efficacy of Acetylsalicylic acid can be decreased when used in combination with Bromfenac.
AlclofenacThe risk or severity of adverse effects can be increased when Bromfenac is combined with Alclofenac.
AminophenazoneThe risk or severity of adverse effects can be increased when Bromfenac is combined with Aminophenazone.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Bromfenac sodium8ECV571Y37120638-55-3PPOSVVJOVKVBPW-UHFFFAOYSA-L
International/Other Brands
Duract (Wyeth-Ayerst)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BromdaySolution / drops0.9 mg/1mLOphthalmicUnit Dose Services2010-09-20Not applicableUS flag
BromdaySolution / drops0.9 mg/1mLOphthalmicBauch & Lomb Incorporated2010-09-202014-10-31US flag
BromdaySolution / drops0.9 mg/1mLOphthalmicPhysicians Total Care, Inc.2011-09-30Not applicableUS flag
BromdaySolution / drops0.9 mg/1mLOphthalmicIsta Pharmaceuticals2010-09-202017-12-29US flag
Bromsite 0.075%Solution / drops0.76 mg/1mLOphthalmicSun Pharmaceutical Industries, Inc.2016-05-01Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-bromfenacSolution0.07 % w/vOphthalmicApotex Corporation2023-06-12Not applicableCanada flag
Auro-bromfenacSolution0.07 % w/vOphthalmicAuro Pharma IncNot applicableNot applicableCanada flag
BromfenacSolution / drops0.9 mg/1mLOphthalmicGland Pharma Limited2020-03-17Not applicableUS flag
BromfenacSolution / drops0.75 mg/1mLOphthalmicLupin Pharmaceuticals, Inc.2024-03-01Not applicableUS flag
BromfenacSolution / drops0.9 mg/1mLOphthalmicApotex Corporation2014-06-192017-07-31US flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Pred Phos - BromBromfenac sodium (0.75 mg/1mL) + Prednisolone sodium phosphate (10 mg/1mL)Solution / dropsOphthalmicImprimis Njof, Llc2018-07-02Not applicableUS flag
Pred Phos-Gati-BromBromfenac (0.75 mg/1mL) + Gatifloxacin sesquihydrate (5 mg/1mL) + Prednisolone sodium phosphate (10 mg/1mL)Solution / dropsOphthalmicImprimis Njof, Llc2018-07-022019-07-01US flag
Pred-BromBromfenac (0.75 mg/1mL) + Prednisolone acetate (10 mg/1mL)Suspension / dropsOphthalmicImprimisRx NJ2018-02-01Not applicableUS flag
Pred-BromBromfenac sodium (0.75 mg/1mL) + Prednisolone acetate (10 mg/1mL)Suspension / dropsOphthalmicImprimis Njof, Llc2018-01-05Not applicableUS flag
Pred-Gati-BromBromfenac sodium (0.75 mg/1mL) + Gatifloxacin sesquihydrate (5 mg/1mL) + Prednisolone acetate (10 mg/1mL)Suspension / dropsOphthalmicImprimis Njof, Llc2018-01-122019-07-01US flag

Categories

ATC Codes
S01BC11 — Bromfenac
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Amine / Amino acid / Amino acid or derivatives / Aniline or substituted anilines / Aromatic homomonocyclic compound / Aryl bromide / Aryl halide / Aryl ketone / Aryl-phenylketone / Benzophenone
show 20 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
organobromine compound, benzophenones, substituted aniline, aromatic amino acid (CHEBI:240107)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
864P0921DW
CAS number
91714-94-2
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

References

Synthesis Reference

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

US20070082857
General References
  1. Wan Po, AL. (2007). Postmarketing Surveillance. In Comprehensive Medicinal Chemistry II (pp. 755-777). Elsevier.
  2. Code of Federal Regulations 216.24: Drug products withdrawn or removed from the market for reasons of safety or effectiveness. [Link]
Human Metabolome Database
HMDB0015098
KEGG Drug
D07541
PubChem Compound
60726
PubChem Substance
46508121
ChemSpider
54730
BindingDB
50248104
RxNav
19737
ChEBI
240107
ChEMBL
CHEMBL1077
ZINC
ZINC000002570817
Therapeutic Targets Database
DAP000732
PharmGKB
PA448670
PDBe Ligand
27R
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Bromfenac
PDB Entries
4mjq
FDA label
Download (41.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableVitrectomy therapy1
4CompletedPreventionCataracts1
4CompletedPreventionCystoid Macular Edema Following Cataract Surgery1
4CompletedPreventionMacular Edema, Cystoid / Retinal Thickening1
4CompletedSupportive CareIntravitreal Injections (IVT) / IVI1

Pharmacoeconomics

Manufacturers
  • Ista pharmaceuticals
Packagers
  • Bausch & Lomb Inc.
  • ISTA Pharmaceuticals
Dosage Forms
FormRouteStrength
Solution / dropsOphthalmic0.9 mg/1mL
Solution / dropsOphthalmic0.75 mg/1mL
Solution / dropsOphthalmic1.035 mg/1mL
Solution / dropsOphthalmic0.805 mg/1mL
Solution / dropsOphthalmic0.76 mg/1mL
Solution / dropsOphthalmic
Suspension / dropsOphthalmic
SolutionOphthalmic0.07 % w/v
Solution / dropsOphthalmic0.7 mg/1mL
SolutionOphthalmic0.9 mg/1mL
Solution / dropsOphthalmic
Solution / dropsOphthalmic0.9 MG/ML
SolutionOphthalmic0.900 mg
SolutionConjunctival; Ophthalmic0.9 mg
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)Region
US8927606No2015-01-062024-01-16US flag
US8871813No2014-10-282024-01-16US flag
US8129431No2012-03-062025-09-11US flag
US9144609No2015-09-292024-01-16US flag
US8669290No2014-03-112024-01-16US flag
US8754131No2014-06-172024-01-16US flag
US8778999No2014-07-152029-09-03US flag
US9517220No2016-12-132033-11-11US flag
US9561277No2017-02-072024-01-16US flag
US10085958No2018-10-022032-11-19US flag

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-MSsplash10-001i-2942000000-55d5af00fe6fa398bead
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0109000000-21ef7d5e8095f307f340
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0092000000-6be713002ca82144414c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0924000000-5a7f90f463b5c2373c7a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0550-5893000000-c5e28489c7260b80ebac
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0920000000-df2748f4fbb1d707376c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9431000000-d53be57fe4b96b92c1a6
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-172.3338708
predicted
DarkChem Lite v0.1.0
[M-H]-164.6479
predicted
DeepCCS 1.0 (2019)
[M+H]+173.2787708
predicted
DarkChem Lite v0.1.0
[M+H]+167.006
predicted
DeepCCS 1.0 (2019)
[M+Na]+172.9845708
predicted
DarkChem Lite v0.1.0
[M+Na]+173.09917
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Enzymes

Kind
Protein
Organism
Humans
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48