Bromfenac Sodium

Names

[ Name ]:
Bromfenac Sodium

[Synonym ]:
Bromfenacsodium
BENZENEACETIC ACID, 2-AMINO-3-(4-BROMOBENZOYL)-, MONOSODIUM SALT
BENZENEACETIC ACID,2-AMINO-3-(4-BROMOBENZOYL)-, SODIUM SALT (1:1)
bromfenac sodium salt
{2-amino-3-[(4-bromophényl)carbonyl]phényl}acétate de sodium
sodium {2-amino-3-[(4-bromophenyl)carbonyl]phenyl}acetate
Sodium [2-amino-3-(4-bromobenzoyl)phenyl]acetate
Natrium-{2-amino-3-[(4-bromphenyl)carbonyl]phenyl}acetat
Bronuck
Benzeneacetic acid, 2-amino-3-(4-bromobenzoyl)-, sodium salt (1:1)
Bromfenac sodium

Biological Activity

[Description]:

Bromfenac sodium is a potent and orally active inhibitor of COX, with IC50s of 5.56 and 7.45 nM for COX-1 and COX-2, respectively. Bromfenac sodium is a brominated non-steroidal anti-inflammatory/analgesic drug (NSAID), and it is commonly used for the research of postoperative inflammation and pain following cataract surgery, and pseudophakic cystoid macular edema (CME)[1][2].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Immunology/Inflammation >> COX

[Target]

COX-1:5.56 nM (IC50)

COX-2:7.45 nM (IC50)

[In Vitro]

Bromfenac (90 μg/mL; 48 h) inhibits TGF-b1-induced extracellular matrix (ECM) synthesis and myoﬁbroblast activation in HConFs and HPFs[3]. Bromfenac (30-90 μg/mL; 48 h) decreases the protein and mRNA expression levels of FN, COL3, a-SMA, and survivin in a dose-dependent manner in HConFs and HPFs[3]. Bromfenac (30-90 μg/mL; 48 h) declines the phosphorylated protein levels of AKT, ERK1/2, and GSK-3b-S9 with dosage in HPFs and HConFs[3].

[In Vivo]

Bromfenac (0.0032-3.16%; 100 or 200 μL; rubbed onto the backs) produces significant anti-inflammatory activity at concentrations as low as 0.1% (4 h pretreatment time) or 0.32% (18h pretreatment time) in rats[2]. Bromfenac (0.032-3.16%; 100 μL; rubbed onto the paws) produces dose-related anti-inflammatory activity in rats[2]. Bromfenac (0.032-1.0%; 50 μL) is 26 times more potent than indomethacin in blocking the erythema when applied directly onto the skin area exposed to UV light in guinea pigs[2]. Bromfenac (0.0032-0.1%; 50μL; rubbed onto the uninjected paw for 4 h per day and 5 days per week) produces a dose and time dependent reduction in the paw volume of both hind limbs in rats[2]. Bromfenac (0.32%; 50μL; rubbed onto the abdomen) produces significant blockade of abdominal constriction to ACh challenge in mice[2]. Animal Model: Male Sprague-Dawley rats (150-250 g) are injected carrageenan[2] Dosage: 0.0032, 0.01, 0.032, 0.1, 0.32, 1.0, 3.16% (100 or 200 μL) Administration: Rubbed onto the backs before 1-72 h of injected carrageenan Result: Produced significant anti-inflammatory activity when applied 1, 2, and 4 h prior to carrageenan challenge at 0.32%. Applied 1 or 4 h prior to carrageenan challenge was active, but not when applied 24 h (or longer) prior to challenge at 0.2%.

[References]

[1]. Schechter BA, et, al. Use of topical bromfenac for treating ocular pain and inflammation beyond cataract surgery: a review of published studies. Clin Ophthalmol. 2019 Aug 1; 13:1439-1460.

[2]. Nolan JC, et, al. The topical anti-inflammatory and analgesic properties of bromfenac in rodents. Agents Actions. 1988 Aug; 25(1-2): 77-85.

[3]. Chen K, et, al. Bromfenac Inhibits TGF-β1-Induced Fibrotic Effects in Human Pterygium and Conjunctival Fibroblasts. Invest Ophthalmol Vis Sci. 2019 Mar 1; 60(4): 1156-1164.

Chemical & Physical Properties

[ Boiling Point ]:
562.2ºC at 760 mmHg

[ Melting Point ]:
285ºC

[ Molecular Formula ]:
C₁₅H₁₁BrNNaO₃

[ Molecular Weight ]:
356.147

[ Flash Point ]:
293.8ºC

[ Exact Mass ]:
354.981995

[ PSA ]:
83.22000

[ LogP ]:
2.13590

[ Appearance of Characters ]:
faint yellow to dark yellow

[ Vapour Pressure ]:
1.77E-13mmHg at 25°C

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
H2O: ≥5mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H400

[ Precautionary Statements ]:
P273

[ Hazard Codes ]:
N

[ Risk Phrases ]:
50

[ Safety Phrases ]:
61

[ RIDADR ]:
UN 3077 9 / PGIII

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Multiparametric assay using HepaRG cells for predicting drug-induced liver injury.

Toxicol. Lett. 236 , 16-24, (2015)

The utility of HepaRG cells as an in vitro cell-based assay system for assessing drug-induced liver injury (DILI) risk was investigated. Seventeen DILI-positive and 15 DILI-negative drugs were selecte...

Efficacy of ophthalmic nonsteroidal antiinflammatory drugs in suppressing anterior capsule contraction and secondary posterior capsule opacification.

J. Cataract Refract. Surg. 35(9) , 1614-8, (2009)

To evaluate the efficacy of ophthalmic nonsteroidal and steroidal antiinflammatory drugs in preventing anterior capsule contraction and secondary posterior capsule opacification (PCO) using an experim...

Cyclooxygenase (COX)-inhibiting drug reduces HSV-1 reactivation in the mouse eye model.

Curr. Eye Res. 34(3) , 171-6, (2009)

To examine the effects of COX inhibitors on suppressing HSV-1 reactivation in a mouse model.BALB/c mice were latently infected with HSV-1 and treated by 0.1% bromfenac Na eye drops, 0.1% pranoprofen e...