Details
Stereochemistry | ACHIRAL |
Molecular Formula | 2C15H11BrNO3.2Na.3H2O |
Molecular Weight | 766.339 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.[Na+].[Na+].NC1=C(CC([O-])=O)C=CC=C1C(=O)C2=CC=C(Br)C=C2.NC3=C(CC([O-])=O)C=CC=C3C(=O)C4=CC=C(Br)C=C4
InChI
InChIKey=PPOSVVJOVKVBPW-UHFFFAOYSA-L
InChI=1S/2C15H12BrNO3.2Na.3H2O/c2*16-11-6-4-9(5-7-11)15(20)12-3-1-2-10(14(12)17)8-13(18)19;;;;;/h2*1-7H,8,17H2,(H,18,19);;;3*1H2/q;;2*+1;;;/p-2
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C15H12BrNO3 |
Molecular Weight | 334.165 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|---|---|
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 |
|||
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 |
---|---|---|
Acute liver failure. | 2001 May |
|
Ximelagatran: direct thrombin inhibitor. | 2006 |
|
How can 'Hy's law' help the clinician? | 2006 Apr |
|
Hy's law: predicting serious hepatotoxicity. | 2006 Apr |
|
Hepatic disorders in patients treated with COX-2 selective inhibitors or nonselective NSAIDs: a case/noncase analysis of spontaneous reports. | 2006 Aug |
|
Comparison of cyclooxygenase inhibitory activity and ocular anti-inflammatory effects of ketorolac tromethamine and bromfenac sodium. | 2006 Jun |
|
Effects of an opioid (oxycodone/paracetamol) and an NSAID (bromfenac) on driving ability, memory functioning, psychomotor performance, pupil size, and mood. | 2006 Jun |
|
Analgesic and anti-inflammatory effectiveness of nepafenac 0.1% for cataract surgery. | 2007 Dec |
|
A review of the use of ketorolac tromethamine 0.4% in the treatment of post-surgical inflammation following cataract and refractive surgery. | 2007 Dec |
|
Corneal melting and perforation in Stevens Johnson syndrome following topical bromfenac use. | 2007 Sep |
|
In vivo pharmacokinetics and in vitro pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac. | 2007 Sep |
|
Cytotoxicity of ophthalmic solutions with and without preservatives to human corneal endothelial cells, epithelial cells and conjunctival epithelial cells. | 2008 Aug |
|
24-hour evaluation of the ocular distribution of (14)C-labeled bromfenac following topical instillation into the eyes of New Zealand White rabbits. | 2008 Aug |
|
Topical ophthalmic NSAIDs: a discussion with focus on nepafenac ophthalmic suspension. | 2008 Jun |
|
Topical ocular delivery of NSAIDs. | 2008 Jun |
|
Off-label promotion, on-target sales. | 2008 Oct 28 |
|
Comparison of ketorolac 0.4% and bromfenac 0.09% at trough dosing: aqueous drug absorption and prostaglandin E2 levels. | 2008 Sep |
|
Etiology and treatment of the inflammatory causes of cystoid macular edema. | 2009 |
|
Management of ocular inflammation and pain following cataract surgery: focus on bromfenac ophthalmic solution. | 2009 |
|
Randomized controlled trial design in rheumatoid arthritis: the past decade. | 2009 |
|
Gateways to clinical trials. | 2009 Apr |
|
Evaluation of the potential for drug-induced liver injury based on in vitro covalent binding to human liver proteins. | 2009 Dec |
|
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles. | 2009 Dec 2 |
|
Topical bromfenac 0.09% vs. ketorolac 0.4% for the control of pain, photophobia, and discomfort following PRK. | 2009 Feb |
|
Concentration and dosing of ketorolac versus bromfenac. | 2009 Jul |
|
Aqueous prostaglandin E(2) of cataract patients at trough ketorolac and bromfenac levels after 2 days dosing. | 2009 Jun |
|
Comparison of efficacy of bromfenac sodium 0.1% ophthalmic solution and fluorometholone 0.02% ophthalmic suspension for the treatment of allergic conjunctivitis. | 2009 Jun |
|
Psychoactive medication and traffic safety. | 2009 Mar |
|
Cyclooxygenase (COX)-inhibiting drug reduces HSV-1 reactivation in the mouse eye model. | 2009 Mar |
|
Information about ADRs explored by pharmacovigilance approaches: a qualitative review of studies on antibiotics, SSRIs and NSAIDs. | 2009 Mar 3 |
|
Effect of bromfenac ophthalmic solution on ocular inflammation following cataract surgery. | 2009 May |
|
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 |
|
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 |
|
Ophthalmic utility of topical bromfenac, a twice-daily nonsteroidal anti-inflammatory agent. | 2009 Oct |
|
Differential effects of non-steroidal anti-inflammatory drugs on mitochondrial dysfunction during oxidative stress. | 2009 Oct 1 |
|
Efficacy of ophthalmic nonsteroidal antiinflammatory drugs in suppressing anterior capsule contraction and secondary posterior capsule opacification. | 2009 Sep |
|
Efficacy of bromfenac sodium ophthalmic solution in preventing cystoid macular oedema after cataract surgery in patients with diabetes. | 2010 Dec |
|
Ocular pharmacokinetics of 0.45% ketorolac tromethamine. | 2010 Dec 1 |
|
Non-steroidal anti-inflammatory drugs: What is the actual risk of liver damage? | 2010 Dec 7 |
|
NSAIDs in combination therapy for the treatment of chronic pseudophakic cystoid macular edema. | 2010 Feb |
|
Chem2Bio2RDF: a semantic framework for linking and data mining chemogenomic and systems chemical biology data. | 2010 May 17 |
|
Efficacy and safety of bromfenac for the treatment of corneal ulcer pain. | 2010 Oct |
|
Data-driven identification of co-morbidities associated with rheumatoid arthritis in a large US health plan claims database. | 2010 Oct 25 |
|
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 |
|
Cytotoxicity of topical medications used for infection and inflammation control after cataract surgery in cultured corneal endothelial cells. | 2010 Sep |
|
Cytotoxicity of five fluoroquinolone and two nonsteroidal anti-inflammatory benzalkonium chloride-free ophthalmic solutions in four corneoconjunctival cell lines. | 2010 Sep 20 |
|
Difluprednate ophthalmic emulsion 0.05% (Durezol) administered two times daily for managing ocular inflammation and pain following cataract surgery. | 2010 Sep 7 |
|
In vitro approach to assess the potential for risk of idiosyncratic adverse reactions caused by candidate drugs. | 2012 Aug 20 |
|
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 |
|
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.
Substance Class |
Chemical
Created
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Edited
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Record UNII |
8ECV571Y37
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Record Status |
Validated (UNII)
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Record Version |
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EMA ASSESSMENT REPORTS |
YELLOX (AUTHORIZED: PAIN, POSTOPERATIVE)
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NCI_THESAURUS |
C257
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EMA ASSESSMENT REPORTS |
YELLOX (AUTHORIZED: OPTHALMOLOGIC SURGICAL PROCEDURES)
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8ECV571Y37
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m2667
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47364
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140536
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DTXSID8044206
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11954316
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