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 Non-ophthalmic formulations of bromfenac were withdrawn in the US in 1998 due to cases of severe liver toxicity.2,1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- Approved, Withdrawn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
Structure for Bromfenac (DB00963)
- 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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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Eye inflammation •••••••••••• Management of Ocular pain •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism AProstaglandin G/H synthase 2 inhibitorHumans UProstaglandin G/H synthase 1 inhibitorHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Bromfenac Action Pathway Drug action - Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAceclofenac The risk or severity of adverse effects can be increased when Bromfenac is combined with Aceclofenac. Acemetacin The risk or severity of adverse effects can be increased when Bromfenac is combined with Acemetacin. Acetylsalicylic acid The therapeutic efficacy of Acetylsalicylic acid can be decreased when used in combination with Bromfenac. Alclofenac The risk or severity of adverse effects can be increased when Bromfenac is combined with Alclofenac. Aminophenazone The risk or severity of adverse effects can be increased when Bromfenac is combined with Aminophenazone. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Bromfenac sodium 8ECV571Y37 120638-55-3 PPOSVVJOVKVBPW-UHFFFAOYSA-L - International/Other Brands
- Duract (Wyeth-Ayerst)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bromday Solution / drops 0.9 mg/1mL Ophthalmic Unit Dose Services 2010-09-20 Not applicable US 
Bromday Solution / drops 0.9 mg/1mL Ophthalmic Physicians Total Care, Inc. 2011-09-30 Not applicable US Bromday Solution / drops 0.9 mg/1mL Ophthalmic Ista Pharmaceuticals 2010-09-20 2017-12-29 US Bromday Solution / drops 0.9 mg/1mL Ophthalmic Bauch & Lomb Incorporated 2010-09-20 2014-10-31 US Bromsite 0.075% Solution / drops 0.76 mg/1mL Ophthalmic Sun Pharmaceutical Industries, Inc. 2016-05-01 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-bromfenac Solution 0.07 % w/v Ophthalmic Apotex Corporation 2023-06-12 Not applicable Canada 
Auro-bromfenac Solution 0.07 % w/v Ophthalmic Auro Pharma Inc Not applicable Not applicable Canada Bromfenac Solution / drops 0.9 mg/1mL Ophthalmic Aurobindo Pharma Limited 2022-03-18 Not applicable US Bromfenac Solution / drops 0.9 mg/1mL Ophthalmic Bauch & Lomb Incorporated 2013-10-16 2015-09-30 US Bromfenac Solution / drops 1.035 mg/1mL Ophthalmic Alembic Pharmaceuticals Limited 2022-11-10 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Pred Phos - Brom Bromfenac sodium (0.75 mg/1mL) + Prednisolone sodium phosphate (10 mg/1mL) Solution / drops Ophthalmic Imprimis Njof, Llc 2018-07-02 Not applicable US Pred Phos-Gati-Brom Bromfenac (0.75 mg/1mL) + Gatifloxacin sesquihydrate (5 mg/1mL) + Prednisolone sodium phosphate (10 mg/1mL) Solution / drops Ophthalmic Imprimis Njof, Llc 2018-07-02 2019-07-01 US Pred-Brom Bromfenac (0.75 mg/1mL) + Prednisolone acetate (10 mg/1mL) Suspension / drops Ophthalmic ImprimisRx NJ 2018-02-01 Not applicable US Pred-Brom Bromfenac sodium (0.75 mg/1mL) + Prednisolone acetate (10 mg/1mL) Suspension / drops Ophthalmic Imprimis Njof, Llc 2018-01-05 Not applicable US Pred-Gati-Brom Bromfenac (0.75 mg/1mL) + Gatifloxacin hemihydrate (5 mg/1mL) + Prednisolone acetate (10 mg/1mL) Suspension / drops Ophthalmic ImprimisRx NJ 2018-01-01 Not applicable US
Categories
- ATC Codes
- S01BC11 — Bromfenac
- Drug Categories
- Agents causing hyperkalemia
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
- Antirheumatic Agents
- Benzene Derivatives
- Central Nervous System Agents
- Cyclooxygenase Inhibitors
- Hydrocarbons, Brominated
- Hydrocarbons, Halogenated
- Ketones
- Nephrotoxic agents
- Ophthalmologicals
- Peripheral Nervous System Agents
- Selective Cyclooxygenase 2 Inhibitors (NSAIDs)
- Sensory Organs
- Sensory System Agents
- 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
- Wan Po, AL. (2007). Postmarketing Surveillance. In Comprehensive Medicinal Chemistry II (pp. 755-777). Elsevier.
- Code of Federal Regulations 216.24: Drug products withdrawn or removed from the market for reasons of safety or effectiveness. [Link]
- External Links
- Human Metabolome Database
- HMDB0015098
- KEGG Drug
- D07541
- PubChem Compound
- 60726
- PubChem Substance
- 46508121
- ChemSpider
- 54730
- BindingDB
- 50248104
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Vitrectomy therapy 1 4 Completed Prevention Cataracts 1 4 Completed Prevention Cystoid Macular Edema Following Cataract Surgery 1 4 Completed Prevention Macular Edema, Cystoid / Retinal Thickening 1 4 Completed Supportive Care Intravitreal Injections (IVT) / IVI 1
Pharmacoeconomics
- Manufacturers
- Ista pharmaceuticals
- Packagers
- Bausch & Lomb Inc.
- ISTA Pharmaceuticals
- Dosage Forms
Form Route Strength Solution / drops Ophthalmic 0.9 mg/1mL Solution / drops Ophthalmic 1.035 mg/1mL Solution / drops Ophthalmic 0.805 mg/1mL Solution / drops Ophthalmic 0.76 mg/1mL Solution / drops Ophthalmic Suspension / drops Ophthalmic Solution Ophthalmic 0.07 % w/v Solution / drops Ophthalmic 0.7 mg/1mL Solution Ophthalmic 0.9 mg/1mL Solution / drops Ophthalmic Solution / drops Ophthalmic 0.9 MG/ML Solution Ophthalmic 0.900 mg Solution Conjunctival; Ophthalmic 0.9 mg - Prices
Unit description Cost Unit Xibrom 0.09% Solution 5ml Bottle 289.59USD bottle Xibrom 0.09% Solution 2.5ml Bottle 148.56USD bottle Xibrom 0.09% eye drops 68.57USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US8927606 No 2015-01-06 2024-01-16 US US8871813 No 2014-10-28 2024-01-16 US US8129431 No 2012-03-06 2025-09-11 US US9144609 No 2015-09-29 2024-01-16 US US8669290 No 2014-03-11 2024-01-16 US US8754131 No 2014-06-17 2024-01-16 US US8778999 No 2014-07-15 2029-09-03 US US9517220 No 2016-12-13 2033-11-11 US US9561277 No 2017-02-07 2024-01-16 US US10085958 No 2018-10-02 2032-11-19 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 3.4 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0126 mg/mL ALOGPS logP 3 ALOGPS logP 3.66 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 3.81 Chemaxon pKa (Strongest Basic) 1.59 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 80.39 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 80.26 m3·mol-1 Chemaxon Polarizability 29.93 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9133 Blood Brain Barrier + 0.8403 Caco-2 permeable + 0.5999 P-glycoprotein substrate Non-substrate 0.7803 P-glycoprotein inhibitor I Non-inhibitor 0.663 P-glycoprotein inhibitor II Non-inhibitor 0.8983 Renal organic cation transporter Non-inhibitor 0.921 CYP450 2C9 substrate Non-substrate 0.8624 CYP450 2D6 substrate Non-substrate 0.898 CYP450 3A4 substrate Non-substrate 0.7483 CYP450 1A2 substrate Non-inhibitor 0.7326 CYP450 2C9 inhibitor Non-inhibitor 0.6515 CYP450 2D6 inhibitor Non-inhibitor 0.9003 CYP450 2C19 inhibitor Non-inhibitor 0.8688 CYP450 3A4 inhibitor Non-inhibitor 0.8927 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7996 Ames test Non AMES toxic 0.88 Carcinogenicity Non-carcinogens 0.7301 Biodegradation Not ready biodegradable 0.9618 Rat acute toxicity 2.5564 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9747 hERG inhibition (predictor II) Non-inhibitor 0.8313
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-001i-2942000000-55d5af00fe6fa398bead Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0109000000-21ef7d5e8095f307f340 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0092000000-6be713002ca82144414c Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0924000000-5a7f90f463b5c2373c7a Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0550-5893000000-c5e28489c7260b80ebac Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0920000000-df2748f4fbb1d707376c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-9431000000-d53be57fe4b96b92c1a6 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 172.3338708 predictedDarkChem Lite v0.1.0 [M-H]- 164.6479 predictedDeepCCS 1.0 (2019) [M+H]+ 173.2787708 predictedDarkChem Lite v0.1.0 [M+H]+ 167.006 predictedDeepCCS 1.0 (2019) [M+Na]+ 172.9845708 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.09917 predictedDeepCCS 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
- 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]
- 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]
- 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
- 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]
- 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
- 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 February 20, 2024 23:55