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)
| 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 |
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 |
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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 |
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 Health Status: unhealthy Age Group: 23.7 years Sex: M+F 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 |
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) Health Status: unhealthy Age Group: 72.2 years (range: 24–95 years) Sex: M+F 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 |
| Drowsiness | 1 patient | 200 mg single, oral Highest studied dose |
unhealthy, 23.7 years Health Status: unhealthy Age Group: 23.7 years Sex: M+F Sources: |
| Headache | 1 patient | 200 mg single, oral Highest studied dose |
unhealthy, 23.7 years Health Status: unhealthy Age Group: 23.7 years Sex: M+F Sources: |
| Hypotension | 1 patient | 200 mg single, oral Highest studied dose |
unhealthy, 23.7 years Health Status: unhealthy Age Group: 23.7 years Sex: M+F Sources: |
| Nausea | 1 patient | 200 mg single, oral Highest studied dose |
unhealthy, 23.7 years Health Status: unhealthy Age Group: 23.7 years Sex: M+F Sources: |
| Vomiting | 1 patient | 200 mg single, oral Highest studied dose |
unhealthy, 23.7 years Health Status: unhealthy Age Group: 23.7 years Sex: M+F Sources: |
| Dizziness | 2 patients | 200 mg single, oral Highest studied dose |
unhealthy, 23.7 years Health Status: unhealthy Age Group: 23.7 years Sex: M+F 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 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >100 uM] | ||||
| no [IC50 >100 uM] | ||||
| no [IC50 >100 uM] | ||||
| no [IC50 >100 uM] | ||||
| no [IC50 >133 uM] | ||||
| no [IC50 >133 uM] | ||||
Page: 128.0 |
no | |||
| weak [IC50 77 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Multiparametric assay using HepaRG cells for predicting drug-induced liver injury. | 2015-07-02 |
|
| 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. | 2014-01 |
|
| In vitro approach to assess the potential for risk of idiosyncratic adverse reactions caused by candidate drugs. | 2012-08-20 |
|
| Non-steroidal anti-inflammatory drugs: What is the actual risk of liver damage? | 2010-12-07 |
|
| Ocular pharmacokinetics of 0.45% ketorolac tromethamine. | 2010-12-01 |
|
| Efficacy of bromfenac sodium ophthalmic solution in preventing cystoid macular oedema after cataract surgery in patients with diabetes. | 2010-12 |
|
| Use of nepafenac (Nevanac) in combination with intravitreal anti-VEGF agents in the treatment of recalcitrant exudative macular degeneration requiring monthly injections. | 2010-10-28 |
|
| Data-driven identification of co-morbidities associated with rheumatoid arthritis in a large US health plan claims database. | 2010-10-25 |
|
| Efficacy and safety of bromfenac for the treatment of corneal ulcer pain. | 2010-10 |
|
| Cytotoxicity of five fluoroquinolone and two nonsteroidal anti-inflammatory benzalkonium chloride-free ophthalmic solutions in four corneoconjunctival cell lines. | 2010-09-20 |
|
| Difluprednate ophthalmic emulsion 0.05% (Durezol) administered two times daily for managing ocular inflammation and pain following cataract surgery. | 2010-09-07 |
|
| Cytotoxicity of topical medications used for infection and inflammation control after cataract surgery in cultured corneal endothelial cells. | 2010-09 |
|
| Chem2Bio2RDF: a semantic framework for linking and data mining chemogenomic and systems chemical biology data. | 2010-05-17 |
|
| NSAIDs in combination therapy for the treatment of chronic pseudophakic cystoid macular edema. | 2010-02 |
|
| Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles. | 2009-12-02 |
|
| Evaluation of the potential for drug-induced liver injury based on in vitro covalent binding to human liver proteins. | 2009-12 |
|
| Retrospective review of the efficacy of topical bromfenac (0.09%) as an adjunctive therapy for patients with neovascular age-related macular degeneration. | 2009-11-10 |
|
| Differential effects of non-steroidal anti-inflammatory drugs on mitochondrial dysfunction during oxidative stress. | 2009-10-01 |
|
| Vitreous nonsteroidal antiinflammatory drug concentrations and prostaglandin E2 levels in vitrectomy patients treated with ketorolac 0.4%, bromfenac 0.09%, and nepafenac 0.1%. | 2009-10 |
|
| Ophthalmic utility of topical bromfenac, a twice-daily nonsteroidal anti-inflammatory agent. | 2009-10 |
|
| Efficacy of ophthalmic nonsteroidal antiinflammatory drugs in suppressing anterior capsule contraction and secondary posterior capsule opacification. | 2009-09 |
|
| Concentration and dosing of ketorolac versus bromfenac. | 2009-07 |
|
| Aqueous prostaglandin E(2) of cataract patients at trough ketorolac and bromfenac levels after 2 days dosing. | 2009-06 |
|
| Comparison of efficacy of bromfenac sodium 0.1% ophthalmic solution and fluorometholone 0.02% ophthalmic suspension for the treatment of allergic conjunctivitis. | 2009-06 |
|
| Effect of bromfenac ophthalmic solution on ocular inflammation following cataract surgery. | 2009-05 |
|
| Gateways to clinical trials. | 2009-04 |
|
| Information about ADRs explored by pharmacovigilance approaches: a qualitative review of studies on antibiotics, SSRIs and NSAIDs. | 2009-03-03 |
|
| Psychoactive medication and traffic safety. | 2009-03 |
|
| Cyclooxygenase (COX)-inhibiting drug reduces HSV-1 reactivation in the mouse eye model. | 2009-03 |
|
| Topical bromfenac 0.09% vs. ketorolac 0.4% for the control of pain, photophobia, and discomfort following PRK. | 2009-02 |
|
| 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 |
|
| Ocular pharmacokinetics of a single dose of bromfenac sodium ophthalmic solution 0.1% in human aqueous humor. | 2008-12 |
|
| Off-label promotion, on-target sales. | 2008-10-28 |
|
| Comparison of ketorolac 0.4% and bromfenac 0.09% at trough dosing: aqueous drug absorption and prostaglandin E2 levels. | 2008-09 |
|
| Cytotoxicity of ophthalmic solutions with and without preservatives to human corneal endothelial cells, epithelial cells and conjunctival epithelial cells. | 2008-08 |
|
| 24-hour evaluation of the ocular distribution of (14)C-labeled bromfenac following topical instillation into the eyes of New Zealand White rabbits. | 2008-08 |
|
| Re: Pharmacokinetics and pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac. | 2008-08 |
|
| Topical ophthalmic NSAIDs: a discussion with focus on nepafenac ophthalmic suspension. | 2008-06 |
|
| Topical ocular delivery of NSAIDs. | 2008-06 |
|
| Effects of nonsteroidal ophthalmic drops on epithelial healing and pain in patients undergoing bilateral photorefractive keratectomy (PRK). | 2008-01-01 |
|
| Development of an in vitro assay for the investigation of metabolism-induced drug hepatotoxicity. | 2008-01 |
|
| Analgesic and anti-inflammatory effectiveness of nepafenac 0.1% for cataract surgery. | 2007-12 |
|
| A review of the use of ketorolac tromethamine 0.4% in the treatment of post-surgical inflammation following cataract and refractive surgery. | 2007-12 |
|
| The systemic safety of bromfenac ophthalmic solution 0.09%. | 2007-12 |
|
| Corneal melting and perforation in Stevens Johnson syndrome following topical bromfenac use. | 2007-09 |
|
| In vivo pharmacokinetics and in vitro pharmacodynamics of nepafenac, amfenac, ketorolac, and bromfenac. | 2007-09 |
|
| Bromfenac ophthalmic solution 0.09% (Xibrom) for postoperative ocular pain and inflammation. | 2007-09 |
|
| Topical bromfenac sodium for long-term management of vernal keratoconjunctivitis. | 2007 |
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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on
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864P0921DW
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Validated (UNII)
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NCI_THESAURUS |
C257
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CFR |
21 CFR 216.24
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NDF-RT |
N0000000160
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N0000175722
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N0000175721
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WHO-VATC |
QS01BC11
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S01BC11
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60726
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BROMFENAC
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C65271
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7131
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CHEMBL1077
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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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Bromfenac
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ACTIVE MOIETY |
| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Biological Half-life | PHARMACOKINETIC |
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