Bromfenac sodium | AHR-10282| CAS# 91714-93-1 | 91714-94-2

Bromfenac sodium
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 317352

CAS#: 91714-93-1 (sodium)

Description: Bromfenac is a non-steroidal anti-inflammatory drug (NSAID) marketed in the US as an ophthalmic solution by ISTA Pharmaceuticals for short-term, local use. Prolensa and Bromday are the once-daily formulation of bromfenac, while Xibrom was approved for twice-daily administration. Bromfenac is indicated for the treatment of ocular inflammation and pain after cataract surgery, though it may be prescribed in an off-label manner by the physician. The high degree of penetration and potency of bromfenac can be attributed to the halogenation of the molecule: by adding a bromine moiety the NSAID becomes highly lipophilic which allows for rapid, sustained drug levels in the ocular tissues.

Chemical Structure

Bromfenac sodium

CAS# 91714-93-1 (sodium)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317352
Name: Bromfenac sodium
CAS#: 91714-93-1 (sodium)
Chemical Formula: C15H11BrNNaO3
Exact Mass: 333.00
Molecular Weight: 356.151
Elemental Analysis: C, 50.59; H, 3.11; Br, 22.44; N, 3.93; Na, 6.46; O, 13.48

Price and Availability

Size	Price	Availability
10mg	USD 175	2 Weeks
25mg	USD 400	2 Weeks
50mg	USD 550	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 91714-94-2 (free base) 91714-93-1 (sodium)

Synonym: Bromfenac sodium, Prolensa, Bromday, Xibrom, AHR-10282, AHR10282, AHR 10282

IUPAC/Chemical Name: 2-Amino-3-(4-bromobenzoyl)benzeneacetic acid sodium

InChi Key: HZFGMQJYAFHESD-UHFFFAOYSA-M

InChi Code: InChI=1S/C15H12BrNO3.Na/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);/q;+1/p-1

SMILES Code: O=C(O)CC1=CC=CC(C(C2=CC=C(Br)C=C2)=O)=C1N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

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Product Data:

Product Data

Instruction:

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Biological target:	Bromfenac sodium is an inhibitor of COX, with IC50s of 5.56 and 7.45 nM for COX-1 and COX-2, respectively.
In vitro activity:	Bromfenac suppressed the TGF-β1-induced protein expression of FN (0.59 ± 0.07 folds, P = 0.008), COL3 (0.48 ± 0.08 folds, P = 0.001), and α-SMA (0.61 ± 0.03 folds, P = 0.008) in HPFs. Bromfenac also attenuated TGF-β1-induced cell migration (0.30 ± 0.07 folds, P < 0.001), cell proliferation (0.64 ± 0.03 folds, P = 0.002) and the expression levels of p-AKT (0.66 ± 0.08 folds, P = 0.032), p-ERK1/2 (0.69 ± 0.11 folds, P = 0.003), and p-GSK-3β-S9 (0.65 ± 0.10 folds, P = 0.002) in HPFs. Reference: Invest Ophthalmol Vis Sci. 2019 Mar 1;60(4):1156-1164. https://pubmed.ncbi.nlm.nih.gov/30908581/
In vivo activity:	Adult albino rats were divided into the following groups (n = 8 retinas/group): (1) intact, (2) intact and bromfenac treatment (twice a day during 7 days), (3) ONC (7 days), and (4) ONC (7 days) + bromfenac treatment (twice a day during 7 days). Quantification of Brn3a (brain-specific homeobox/POU domain protein 3A) +RGCs (retinal ganglion cells) in cross sections showed that bromfenac treatment does not accelerate ONC-induced degeneration. Cellular retinaldehyde binding protein 1 regulation indicated that bromfenac improves retinal homeostasis in injured retinas. Spectral-domain OCT showed that the thickness of the retina and the retinal nerve fiber layer at 7 days post ONC was significantly reduced in bromfenac-treated animals when compared to untreated animals. Reference: Invest Ophthalmol Vis Sci. 2016 Nov 1;57(14):6098-6106. https://pubmed.ncbi.nlm.nih.gov/27832276/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Ethanol	2.0	5.62
	Water	71.0	199.35

Preparing Stock Solutions

The following data is based on the product molecular weight 356.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Chen K, Lai K, Zhang X, Qin Z, Fu Q, Luo C, Jin X, Hu J, Liu S, Yao K. Bromfenac Inhibits TGF-β1-Induced Fibrotic Effects in Human Pterygium and Conjunctival Fibroblasts. Invest Ophthalmol Vis Sci. 2019 Mar 1;60(4):1156-1164. doi: 10.1167/iovs.18-24743. PMID: 30908581. 2. Rovere G, Nadal-Nicolás FM, Sobrado-Calvo P, García-Bernal D, Villegas-Pérez MP, Vidal-Sanz M, Agudo-Barriuso M. Topical Treatment With Bromfenac Reduces Retinal Gliosis and Inflammation After Optic Nerve Crush. Invest Ophthalmol Vis Sci. 2016 Nov 1;57(14):6098-6106. doi: 10.1167/iovs.16-20425. PMID: 27832276.
In vitro protocol:	1. Chen K, Lai K, Zhang X, Qin Z, Fu Q, Luo C, Jin X, Hu J, Liu S, Yao K. Bromfenac Inhibits TGF-β1-Induced Fibrotic Effects in Human Pterygium and Conjunctival Fibroblasts. Invest Ophthalmol Vis Sci. 2019 Mar 1;60(4):1156-1164. doi: 10.1167/iovs.18-24743. PMID: 30908581.
In vivo protocol:	1. Rovere G, Nadal-Nicolás FM, Sobrado-Calvo P, García-Bernal D, Villegas-Pérez MP, Vidal-Sanz M, Agudo-Barriuso M. Topical Treatment With Bromfenac Reduces Retinal Gliosis and Inflammation After Optic Nerve Crush. Invest Ophthalmol Vis Sci. 2016 Nov 1;57(14):6098-6106. doi: 10.1167/iovs.16-20425. PMID: 27832276.

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1: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Bromfenac. 2018 Dec 3. PMID: 30000016.

2: Sheppard JD. Topical bromfenac for prevention and treatment of cystoid macular edema following cataract surgery: a review. Clin Ophthalmol. 2016 Oct 25;10:2099-2111. doi: 10.2147/OPTH.S86971. PMID: 27822006; PMCID: PMC5087782.

3: Hoy SM. Bromfenac Ophthalmic Solution 0.07%: A Review of Its Use After Cataract Surgery. Clin Drug Investig. 2015 Aug;35(8):525-9. doi: 10.1007/s40261-015-0309-3. PMID: 26177719.

4: Jones J, Francis P. Ophthalmic utility of topical bromfenac, a twice-daily nonsteroidal anti-inflammatory agent. Expert Opin Pharmacother. 2009 Oct;10(14):2379-85. doi: 10.1517/14656560903188425. PMID: 19735215.

5: Raj N, Panigrahi A, Alam M, Gupta N. Bromfenac-induced neurotrophic keratitis in a corneal graft. BMJ Case Rep. 2022 Jul 11;15(7):e249400. doi: 10.1136/bcr-2022-249400. PMID: 35817488; PMCID: PMC9274534.

6: Saade JS, Istambouli R, AbdulAal M, Antonios R, Hamam RN. Bromfenac 0.09% for the Treatment of Macular Edema Secondary to Noninfectious Uveitis. Middle East Afr J Ophthalmol. 2021 Sep 25;28(2):98-103. doi: 10.4103/meajo.meajo_134_21. PMID: 34759667; PMCID: PMC8547661.

7: Rajpal RK, Ross B, Rajpal SD, Hoang K. Bromfenac ophthalmic solution for the treatment of postoperative ocular pain and inflammation: safety, efficacy, and patient adherence. Patient Prefer Adherence. 2014 Jun 25;8:925-31. doi: 10.2147/PPA.S46667. PMID: 25028541; PMCID: PMC4077855.

8: Wentz SM, Price F, Harris A, Siesky B, Ciulla T. Efficacy and safety of bromfenac 0.075% formulated in DuraSite for pain and inflammation in cataract surgery. Expert Opin Pharmacother. 2019 Oct;20(14):1703-1709. doi: 10.1080/14656566.2019.1645834. Epub 2019 Jul 25. PMID: 31343372.

9: Aguilar Sierra MC, Alvarado-Villacorta R, Pastrana CP. Topical Bromfenac Sodium in Femtosecond Laser-Assisted Cataract Surgery. J Curr Ophthalmol. 2020 Mar 23;32(1):32-37. doi: 10.1016/j.joco.2019.07.007. PMID: 32510011; PMCID: PMC7265276.

10: Skjodt NM, Davies NM. Clinical pharmacokinetics and pharmacodynamics of bromfenac. Clin Pharmacokinet. 1999 Jun;36(6):399-408. doi: 10.2165/00003088-199936060-00002. PMID: 10427465.

11: Gabr AF, Kamel MF, Elbarawy AA. Topical bromfenac as adjunctive treatment with intravitreal ranibizumab for diabetic macular edema. Int Ophthalmol. 2023 Apr 21. doi: 10.1007/s10792-023-02722-1. Epub ahead of print. PMID: 37083870.

12: Walters TR, Goldberg DF, Peace JH, Gow JA; Bromfenac Ophthalmic Solution 0.07% Once Daily Study Group. Bromfenac ophthalmic solution 0.07% dosed once daily for cataract surgery: results of 2 randomized controlled trials. Ophthalmology. 2014 Jan;121(1):25-33. doi: 10.1016/j.ophtha.2013.07.006. Epub 2013 Sep 8. PMID: 24021896.

13: Matsumura T, Iwasaki K, Arimura S, Takeda R, Takamura Y, Inatani M. Topical bromfenac reduces multiple inflammatory cytokines in the aqueous humour of pseudophakic patients. Sci Rep. 2021 Mar 16;11(1):6018. doi: 10.1038/s41598-021-85495-w. PMID: 33727659; PMCID: PMC7966778.

14: Sánchez-Santos I, García-Sánchez GA, Gonzalez-Salinas R, Linares-Alba MA, Rodríguez-Reyes AA, García-Santisteban R, Tirado-González V, Hernández-Piñamora E, García-Arzate D, Morales-Cantón V, Quiroz-Mercado H. Intravitreal bromfenac liposomal suspension (100 μg / 0.1 ml). A safety study in rabbit eyes. Exp Eye Res. 2020 May;194:108020. doi: 10.1016/j.exer.2020.108020. Epub 2020 Mar 21. PMID: 32209318.

15: Zhang X, Lai K, Li S, Wang J, Li J, Wang W, Ni S, Lu B, Grzybowski A, Ji J, Han H, Yao K. Drug-eluting intraocular lens with sustained bromfenac release for conquering posterior capsular opacification. Bioact Mater. 2021 Jul 23;9:343-357. doi: 10.1016/j.bioactmat.2021.07.015. PMID: 34820575; PMCID: PMC8586266.

16: Chen K, Lai K, Zhang X, Qin Z, Fu Q, Luo C, Jin X, Hu J, Liu S, Yao K. Bromfenac Inhibits TGF-β1-Induced Fibrotic Effects in Human Pterygium and Conjunctival Fibroblasts. Invest Ophthalmol Vis Sci. 2019 Mar 1;60(4):1156-1164. doi: 10.1167/iovs.18-24743. PMID: 30908581.

17: McQuay HJ, Carroll D, Frankland T, Harvey M, Moore A. Bromfenac, acetaminophen, and placebo in orthopedic postoperative pain. Clin Pharmacol Ther. 1990 Jun;47(6):760-6. doi: 10.1038/clpt.1990.105. PMID: 2357869.

18: Rovere G, Nadal-Nicolás FM, Sobrado-Calvo P, Villegas-Pérez MP, Vidal-Sanz M, Agudo-Barriuso M. Topical bromfenac transiently delays axotomy-induced retinal ganglion cell loss. Exp Eye Res. 2019 May;182:156-159. doi: 10.1016/j.exer.2019.03.023. Epub 2019 Mar 30. PMID: 30940447.

19: Patel M, Saha N, Patel S, Ahlawat P, Dharamsi A, Patel A. Development of Bromfenac Sodium Loaded Pluronic Nanomicelles: Characterization and Corneal Permeation Study. Recent Adv Drug Deliv Formul. 2022;16(1):68-78. doi: 10.2174/2667387816666220128123737. PMID: 35088685.

20: Rovere G, Nadal-Nicolás FM, Sobrado-Calvo P, García-Bernal D, Villegas-Pérez MP, Vidal-Sanz M, Agudo-Barriuso M. Topical Treatment With Bromfenac Reduces Retinal Gliosis and Inflammation After Optic Nerve Crush. Invest Ophthalmol Vis Sci. 2016 Nov 1;57(14):6098-6106. doi: 10.1167/iovs.16-20425. PMID: 27832276.

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