Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H12BrNO3 |
Molecular Weight | 334.165 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=C(CC(O)=O)C=CC=C1C(=O)C2=CC=C(Br)C=C2
InChI
InChIKey=ZBPLOVFIXSTCRZ-UHFFFAOYSA-N
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)
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/bromfenac-ophthlamic-solution.html | http://www.rxlist.com/xibrom-drug.htm
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/bromfenac-ophthlamic-solution.html | http://www.rxlist.com/xibrom-drug.htm
Bromfenac is a topical, nonsteroidal anti-inflammatory drug (NSAID) for ophthalmic use. It is indicated for the treatment of postoperative inflammation and reduction of ocular pain in patients who have undergone cataract surgery. The mechanism of its action is thought to be due to its ability to block prostaglandin synthesis by inhibiting cyclooxygenase 1 and 2. The most commonly reported adverse reactions in 3 to 8% of patients were anterior chamber inflammation, foreign body sensation, eye pain, photophobia and vision blurred.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24796327 |
5.56 nM [IC50] | ||
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24796327 |
7.45 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | PROLENSA Approved UseBromfenac Ophthalmic Solution, 0.09% is indicated for the treatment of postoperative inflammation and reduction of ocular pain in patients who have undergone cataract surgery. Bromfenac Ophthalmic Solution is a nonsteroidal anti-inflammatory drug (NSAID) indicated for the treatment of postoperative inflammation and reduction of ocular pain in patients who have undergone cataract extraction (1). Launch Date2013 |
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Primary | PROLENSA Approved UseBromfenac ophthalmic solution (0.07%) is indicated for the treatment of postoperative inflammation and reduction of ocular pain in patients who have undergone cataract surgery. Launch Date2013 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
58.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19049295 |
1 drop single, ocular dose: 1 drop route of administration: Ocular experiment type: SINGLE co-administered: |
BROMFENAC aqueous humor | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
313.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19049295 |
1 drop single, ocular dose: 1 drop route of administration: Ocular experiment type: SINGLE co-administered: |
BROMFENAC aqueous humor | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19049295 |
1 drop single, ocular dose: 1 drop route of administration: Ocular experiment type: SINGLE co-administered: |
BROMFENAC aqueous humor | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.2% |
unknown, unknown |
BROMFENAC plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.09 % 2 times / day steady, ophthalmic Recommended Dose: 0.09 %, 2 times / day Route: ophthalmic Route: steady Dose: 0.09 %, 2 times / day Sources: |
unhealthy, 20 years n = 1 Health Status: unhealthy Age Group: 20 years Sex: F Population Size: 1 Sources: |
Disc. AE: Corneal melt... AEs leading to discontinuation/dose reduction: Corneal melt (1 patient) Sources: |
200 mg single, oral Highest studied dose |
unhealthy, 23.7 years n = 21 Health Status: unhealthy Age Group: 23.7 years Sex: M+F Population Size: 21 Sources: |
Other AEs: Headache, Nausea... Other AEs: Headache (1 patient) Sources: Nausea (1 patient) Dizziness (2 patients) Drowsiness (1 patient) Vomiting (1 patient) Hypotension (1 patient) |
25 mg 4 times / day steady, oral Recommended Dose: 25 mg, 4 times / day Route: oral Route: steady Dose: 25 mg, 4 times / day Sources: |
unhealthy, 60 years n = 1 Health Status: unhealthy Age Group: 60 years Sex: F Population Size: 1 Sources: |
Disc. AE: Hepatitis fulminant... AEs leading to discontinuation/dose reduction: Hepatitis fulminant (grade 5, 1 patient) Sources: |
0.1 % single, ophthalmic Highest studied dose Dose: 0.1 % Route: ophthalmic Route: single Dose: 0.1 % Sources: |
unhealthy, 72.2 years (range: 24–95 years) n = 54 Health Status: unhealthy Condition: cataract Age Group: 72.2 years (range: 24–95 years) Sex: M+F Population Size: 54 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Corneal melt | 1 patient Disc. AE |
0.09 % 2 times / day steady, ophthalmic Recommended Dose: 0.09 %, 2 times / day Route: ophthalmic Route: steady Dose: 0.09 %, 2 times / day Sources: |
unhealthy, 20 years n = 1 Health Status: unhealthy Age Group: 20 years Sex: F Population Size: 1 Sources: |
Drowsiness | 1 patient | 200 mg single, oral Highest studied dose |
unhealthy, 23.7 years n = 21 Health Status: unhealthy Age Group: 23.7 years Sex: M+F Population Size: 21 Sources: |
Headache | 1 patient | 200 mg single, oral Highest studied dose |
unhealthy, 23.7 years n = 21 Health Status: unhealthy Age Group: 23.7 years Sex: M+F Population Size: 21 Sources: |
Hypotension | 1 patient | 200 mg single, oral Highest studied dose |
unhealthy, 23.7 years n = 21 Health Status: unhealthy Age Group: 23.7 years Sex: M+F Population Size: 21 Sources: |
Nausea | 1 patient | 200 mg single, oral Highest studied dose |
unhealthy, 23.7 years n = 21 Health Status: unhealthy Age Group: 23.7 years Sex: M+F Population Size: 21 Sources: |
Vomiting | 1 patient | 200 mg single, oral Highest studied dose |
unhealthy, 23.7 years n = 21 Health Status: unhealthy Age Group: 23.7 years Sex: M+F Population Size: 21 Sources: |
Dizziness | 2 patients | 200 mg single, oral Highest studied dose |
unhealthy, 23.7 years n = 21 Health Status: unhealthy Age Group: 23.7 years Sex: M+F Population Size: 21 Sources: |
Hepatitis fulminant | grade 5, 1 patient Disc. AE |
25 mg 4 times / day steady, oral Recommended Dose: 25 mg, 4 times / day Route: oral Route: steady Dose: 25 mg, 4 times / day Sources: |
unhealthy, 60 years n = 1 Health Status: unhealthy Age Group: 60 years Sex: F Population Size: 1 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Serious liver injury. Leading reason for drug removals, restrictions. | 2001 May-Jun |
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Effects of nonsteroidal anti-inflammatory drugs on experimental allergic conjunctivitis in Guinea pigs. | 2003 Dec |
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Drug-induced hepatotoxicity. | 2003 Jul 31 |
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Gateways to clinical trials. | 2003 Jun |
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Effects of topical corticosteroids and nonsteroidal anti-inflammatory drugs on prostaglandin e2-induced aqueous flare elevation in pigmented rabbits. | 2003 Nov-Dec |
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Drug-induced liver injury. | 2004 Mar 1 |
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Do preclinical testing strategies help predict human hepatotoxic potentials? | 2005 |
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Hy's law: predicting serious hepatotoxicity. | 2006 Apr |
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Hepatic disorders in patients treated with COX-2 selective inhibitors or nonselective NSAIDs: a case/noncase analysis of spontaneous reports. | 2006 Aug |
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Three cases of corneal melting after instillation of a new nonsteroidal anti-inflammatory drug. | 2006 Dec |
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Misuse and abuse of topically applied nonsteroidal anti-inflammatory drugs. | 2006 Dec |
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Ocular permeation and inhibition of retinal inflammation: an examination of data and expert opinion on the clinical utility of nepafenac. | 2006 Feb |
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Three cases of corneal melting after instillation of a new nonsteroidal anti-inflammatory drug. | 2006 Feb |
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Effects of an opioid (oxycodone/paracetamol) and an NSAID (bromfenac) on driving ability, memory functioning, psychomotor performance, pupil size, and mood. | 2006 Jun |
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A review of the use of ketorolac tromethamine 0.4% in the treatment of post-surgical inflammation following cataract and refractive surgery. | 2007 Dec |
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The systemic safety of bromfenac ophthalmic solution 0.09%. | 2007 Dec |
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Effects of topical anti-inflammatory agents in a botulinum toxin B-induced mouse model of keratoconjunctivitis sicca. | 2007 Feb |
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Effects of nonsteroidal ophthalmic drops on epithelial healing and pain in patients undergoing bilateral photorefractive keratectomy (PRK). | 2007 Nov-Dec |
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Cytotoxicity of ophthalmic solutions with and without preservatives to human corneal endothelial cells, epithelial cells and conjunctival epithelial cells. | 2008 Aug |
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Re: Pharmacokinetics and pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac. | 2008 Aug |
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Ocular pharmacokinetics of a single dose of bromfenac sodium ophthalmic solution 0.1% in human aqueous humor. | 2008 Dec |
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Development of an in vitro assay for the investigation of metabolism-induced drug hepatotoxicity. | 2008 Jan |
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Topical ophthalmic NSAIDs: a discussion with focus on nepafenac ophthalmic suspension. | 2008 Jun |
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Off-label promotion, on-target sales. | 2008 Oct 28 |
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Etiology and treatment of the inflammatory causes of cystoid macular edema. | 2009 |
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Management of ocular inflammation and pain following cataract surgery: focus on bromfenac ophthalmic solution. | 2009 |
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Evaluation of the potential for drug-induced liver injury based on in vitro covalent binding to human liver proteins. | 2009 Dec |
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Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles. | 2009 Dec 2 |
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Comparison of efficacy of bromfenac sodium 0.1% ophthalmic solution and fluorometholone 0.02% ophthalmic suspension for the treatment of allergic conjunctivitis. | 2009 Jun |
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Information about ADRs explored by pharmacovigilance approaches: a qualitative review of studies on antibiotics, SSRIs and NSAIDs. | 2009 Mar 3 |
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Effect of bromfenac ophthalmic solution on ocular inflammation following cataract surgery. | 2009 May |
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Retrospective review of the efficacy of topical bromfenac (0.09%) as an adjunctive therapy for patients with neovascular age-related macular degeneration. | 2009 Nov-Dec |
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Vitreous nonsteroidal antiinflammatory drug concentrations and prostaglandin E2 levels in vitrectomy patients treated with ketorolac 0.4%, bromfenac 0.09%, and nepafenac 0.1%. | 2009 Oct |
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Efficacy of bromfenac sodium ophthalmic solution in preventing cystoid macular oedema after cataract surgery in patients with diabetes. | 2010 Dec |
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Efficacy and safety of bromfenac for the treatment of corneal ulcer pain. | 2010 Oct |
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Use of nepafenac (Nevanac) in combination with intravitreal anti-VEGF agents in the treatment of recalcitrant exudative macular degeneration requiring monthly injections. | 2010 Oct 28 |
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Cytotoxicity of topical medications used for infection and inflammation control after cataract surgery in cultured corneal endothelial cells. | 2010 Sep |
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Difluprednate ophthalmic emulsion 0.05% (Durezol) administered two times daily for managing ocular inflammation and pain following cataract surgery. | 2010 Sep 7 |
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In vitro approach to assess the potential for risk of idiosyncratic adverse reactions caused by candidate drugs. | 2012 Aug 20 |
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A correlation between the in vitro drug toxicity of drugs to cell lines that express human P450s and their propensity to cause liver injury in humans. | 2014 Jan |
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Multiparametric assay using HepaRG cells for predicting drug-induced liver injury. | 2015 Jul 2 |
Patents
Sample Use Guides
Instill one drop into the affected eye once daily beginning 1 day prior to surgery, continued on the day of surgery, and through the first 14 days postsurgery.
Route of Administration:
Topical
ARPE-19 cells treated with 4X and 2X clinical doses of bromfenac ophthalmic solution (BOS) showed mean CV of 16.95±3.04% (p<0.001), and 28.45±2.33% (p0.05). The ΔΨM was decreased and the caspase 3 /7 activity increased in ARPE-19 cells treated with all BOS concentrations when compared to untreated ARPE 19 controls (15.15±1.05). The ΔΨM of ARPE-19 cells were 2.74±0.36 (p<0.001), 2.35±0.33 (p<0.001), 2.63±0.20 (p<0.001), 5.30±0.18 (p<0.001) and 5.22±0.15 (p<0.001) for 4X, 2X, X, X/2 and X/4 concentrations respectively. The ROS activity was significantly increased for all BOS concentrations when compared to untreated control. Caspase 3/7 activity was significantly increased for all BOS concentrations.
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Code | English |
Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C257
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NDF-RT |
N0000000160
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NDF-RT |
N0000175722
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NDF-RT |
N0000175721
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WHO-VATC |
QS01BC11
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WHO-ATC |
S01BC11
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60726
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BROMFENAC
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91714-94-2
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C65271
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7131
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CHEMBL1077
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5892
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19737
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100000088693
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C053083
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DB00963
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m2667
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240107
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Bromfenac
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)