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MedKoo Cat#: 413967 | Name: Bromfenac Free Base
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Description:

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

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 Free Base
Bromfenac Free Base
CAS#91714-94-2 (free base)

Theoretical Analysis

MedKoo Cat#: 413967

Name: Bromfenac Free Base

CAS#: 91714-94-2 (free base)

Chemical Formula: C15H12BrNO3

Exact Mass: 333.0001

Molecular Weight: 334.17

Elemental Analysis: C, 53.91; H, 3.62; Br, 23.91; N, 4.19; O, 14.36

Price and Availability

Size Price Availability Quantity
250mg USD 285.00 2 Weeks
1g USD 550.00 2 Weeks
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Related CAS #
91714-94-2 (free base) 91714-93-1 (sodium) 120638-55-3 (sodium hydrate)
Synonym
Bromfenac Free Base; AHR10282; AHR-10282; AHR 10282
IUPAC/Chemical Name
Benzeneacetic acid, 2-amino-3-(4-bromobenzoyl)-
InChi Key
ZBPLOVFIXSTCRZ-UHFFFAOYSA-N
InChi Code
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)
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Bromfenac 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.
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/

Preparing Stock Solutions

The following data is based on the product molecular weight 334.17 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.

Recalculate based on batch purity %
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.
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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NSC-102553

NSC-102553