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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
Structure of BROMFENAC SODIUM

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

HIDE SMILES / InChI

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.56 nM [IC50]
7.45 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROLENSA

Approved Use

Bromfenac 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 Date

2013
Primary
PROLENSA

Approved Use

Bromfenac 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 Date

2013
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
58.4 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
313.8 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.4 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
0.2%
unknown, unknown
BROMFENAC plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
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)
Nausea (1 patient)
Dizziness (2 patients)
Drowsiness (1 patient)
Vomiting (1 patient)
Hypotension (1 patient)
Sources:
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

AEs

AESignificanceDosePopulation
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
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
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
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
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
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
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
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
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
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
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
Dose: 200 mg
Route: oral
Route: single
Dose: 200 mg
Sources:
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:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
by admin
on Fri Dec 15 15:17:10 GMT 2023
Edited
by admin
on Fri Dec 15 15:17:10 GMT 2023
Record UNII
8ECV571Y37
Record Status Validated (UNII)
Record Version
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Name Type Language
BROMFENAC SODIUM
MART.   ORANGE BOOK   USAN   VANDF  
USAN  
Official Name English
BROMFENAC SODIUM [ORANGE BOOK]
Common Name English
BROMFENAC SODIUM SESQUIHYDRATE
EMA EPAR  
Common Name English
BENZENEACETIC ACID, 2-AMINO-3-(4-BROMOBENZOYL)-, SODIUM SALT, HYDRATE (2:2:3)
Common Name English
BROMDAY
Brand Name English
XIBROM
Brand Name English
BROMFENAC SODIUM HYDRATE
JAN  
Common Name English
BROMSITE
Brand Name English
SODIUM (-AMINO-3-(P-BROMOBENZOYL)PHENYL)ACETATE SESQUIHYDRATE
Common Name English
BROMFENAC MONOSODIUM SALT SESQUIHYDRATE [MI]
Common Name English
BROMFENAC SODIUM HYDRATE [JAN]
Common Name English
BENZENEACETIC ACID, 2-AMINO-3-(4-BROMOBENZOYL)-, MONOSODIUM SALT, SESQUIHYDRATE
Common Name English
YELLOX
Brand Name English
BROMFENAC SODIUM [VANDF]
Common Name English
BROMFENAC MONOSODIUM SALT SESQUIHYDRATE
MI  
Common Name English
BROMFENAC SODIUM SESQUIHYDRATE [EMA EPAR]
Common Name English
AHR-10282B
Code English
BROMFENAC SODIUM [USAN]
Common Name English
BROMFENAC SODIUM [MART.]
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS YELLOX (AUTHORIZED: PAIN, POSTOPERATIVE)
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
NCI_THESAURUS C257
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
EMA ASSESSMENT REPORTS YELLOX (AUTHORIZED: OPTHALMOLOGIC SURGICAL PROCEDURES)
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C65272
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
PRIMARY
SMS_ID
100000085124
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
PRIMARY
EVMPD
SUB00874MIG
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
PRIMARY
CAS
120638-55-3
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
PRIMARY
FDA UNII
8ECV571Y37
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
PRIMARY
USAN
X-67
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
PRIMARY
ChEMBL
CHEMBL1077
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
PRIMARY
MERCK INDEX
m2667
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
PRIMARY Merck Index
DRUG BANK
DBSALT000356
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
PRIMARY
CHEBI
59176
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
PRIMARY
RXCUI
47364
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
PRIMARY RxNorm
CHEBI
140536
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID8044206
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
PRIMARY
PUBCHEM
11954316
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
PRIMARY
DAILYMED
8ECV571Y37
Created by admin on Fri Dec 15 15:17:10 GMT 2023 , Edited by admin on Fri Dec 15 15:17:10 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
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IMPURITY -> PARENT
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ACTIVE MOIETY