Bromfenac

Last updated
Bromfenac
Bromfenac.svg
Clinical data
Trade names Bromday, Prolensa (US), Yellox (EU)
AHFS/Drugs.com Monograph
MedlinePlus a611018
License data
Routes of
administration 		Eye drops
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding 99.8%
Metabolism CYP2C9
Metabolites Lactam, others
Elimination half-life 1.4 hours in aqueous humour
Excretion 82% urine, 13% faeces
Identifiers
  • 2-[2-amino-3-(4-bromobenzoyl)phenyl]acetic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C15H12BrNO3
Molar mass 334.169 g·mol−1
3D model (JSmol)
Melting point 284 to 286 °C (543 to 547 °F) (bromfenac sodium·1.5H2O)
  • O=C(c1ccc(Br)cc1)c2cccc(c2N)CC(=O)O
  • 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) Yes check.svgY
  • Key:ZBPLOVFIXSTCRZ-UHFFFAOYSA-N Yes check.svgY
   (verify)

Bromfenac is a nonsteroidal anti-inflammatory drug (NSAID) [1] marketed in the US as an ophthalmic solution (brand names Prolensa and Bromday, [2] prior formulation brand name Xibrom, which has since been discontinued) 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. In the European Union, the brand name is Yellox. Bromfenac is indicated for the treatment of ocular inflammation and pain after cataract surgery. [3]

Contents

Medical uses

Bromfenac is indicated for the treatment of postoperative ocular inflammation following cataract extraction. [4] [5]

The drug has been shown to reduce macular edema and thickness of the retina (an indicator for inflammation) and improve visual acuity after surgery. [6]

Contraindications

Bromfenac is contraindicated for people with adverse reactions to NSAIDs, such as asthma or rashes. [3] [7]

Side effects

Bromfenac eye drops are generally well tolerated. Comparatively common side effects in clinical studies included abnormal sensations in eye (0.5% of people treated with bromfenac), mild to moderate erosion of the cornea (0.4%), eye pruritus (0.4%), eye pain (0.3%) and redness (0.3%). Serious side effects such as corneal perforation were not reported in studies but only during post-marketing in less than one patient in 1000. [3] [7]

Interactions

No systematic interaction studies have been performed. There are no known cases of interactions with antibiotic eye drops. [3] [7] Blood plasma levels remain very low during bromfenac therapy, so interactions with drugs taken by mouth are unlikely.

Pharmacology

Mechanism of action

As an NSAID, bromfenac works by inhibiting prostaglandin synthesis by blocking the cyclooxygenase (COX) enzymes. It preferably acts on COX-2 and only has a low affinity for COX-1. [7]

Pharmacokinetics

Bromfenac lactam, the main metabolite in urine Bromfenac cyclic amide.svg
Bromfenac lactam, the main metabolite in urine

Bromfenac is well absorbed through the cornea and reaches highest concentrations in the aqueous humour after 150 to 180 minutes, with a biological half-life of 1.4 hours and high drug levels being maintained for at least 12 hours. It is mainly concentrated in the aqueous humour and conjunctiva, and much less in the lens and vitreous body. [3] [7]

Concentrations in the blood plasma are too low to be measured quantitatively. 99.8% of the substance are bound to plasma proteins. The enzyme mainly responsible for metabolization of bromfenac is CYP2C9, and metabolites include the lactam and several conjugated compounds. 82% are excreted via the urine, and 13% via the faeces. [3] [7]

Compared to amfenac, the halogenation of bromfenac's chemical structure (the bromine atom at C4) increases its penetration into ocular tissues, and increases its potency for COX enzyme inhibition. [6] [8]

Chemical structures of diclofenac, bromfenac, nepafenac, and amfenac. Brom vs Amf.jpg
Chemical structures of diclofenac, bromfenac, nepafenac, and amfenac.

Chemistry

Along with indomethacin, diclofenac and others, bromfenac belongs to the acetic acid group of NSAIDs. It is used in form of bromfenac sodium · 1.5 H2O (CAS number: 120638-55-3 ), which is soluble in water, methanol and aqueous bases, insoluble in chloroform and aqueous acids, and melts at 284 to 286 °C (543 to 547 °F) under decomposition. [9]

History

For ophthalmic use, bromfenac has been prescribed more than 20,000,000 times across the world. [7] As an eye drop, it has been available since 2000, starting in Japan where it was sold as Bronuck. [10] It was first FDA approved for use in the United States in 2005, and it was marketed as Xibrom, twice-daily. [11] In October 2010 Bromday received FDA approval as a new, once-daily formulation.[ citation needed ] More recently, in 2013, Prolensa has also been approved by the FDA. [11] Bromfenac eye drops have been marketed in the European Union since 2011, [7] and are available on worldwide markets with agreements from Bausch & Lomb, [7] Croma-Pharma, and other companies.[ citation needed ]

Bromfenac was formerly marketed in the United States by Wyeth-Ayerst in an oral formulation called Duract for short-term relief of pain (less than 10 days at a time). It was brought to market in July 1997, and was withdrawn 22 June 1998, following numerous reports of hepatotoxicity in patients who had taken the medication for longer than the recommended 10-day period. [12] [13]

Related Research Articles

<span class="mw-page-title-main">Diclofenac</span> Nonsteroidal anti-inflammatory drug


Diclofenac, sold under the brand name Voltaren, among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain and inflammatory diseases such as gout. It is taken by mouth or rectally in a suppository, used by injection, or applied to the skin. Improvements in pain last for as much as eight hours. It is also available in combination with misoprostol in an effort to decrease stomach problems.

<span class="mw-page-title-main">Prednisolone</span> Chemical compound (steroid medication)

Prednisolone is a corticosteroid, a steroid hormone used to treat certain types of allergies, inflammatory conditions, autoimmune disorders, and cancers. Some of these conditions include adrenocortical insufficiency, high blood calcium, rheumatoid arthritis, dermatitis, eye inflammation, asthma, and multiple sclerosis. It can be taken by mouth, injected into a vein, used topically as a skin cream, or as eye drops. It differs from the similarly named prednisone in having a hydroxyl at the 11th carbon instead of a ketone.

Carbachol, also known as carbamylcholine and sold under the brand name Miostat among others, is a cholinomimetic drug that binds and activates acetylcholine receptors. Thus it is classified as a cholinergic agonist. It is primarily used for various ophthalmic purposes, such as for treating glaucoma, or for use during ophthalmic surgery. It is generally administered as an ophthalmic solution.

<span class="mw-page-title-main">Dry eye syndrome</span> Medical condition

Dry eye syndrome, also known as keratoconjunctivitis sicca, is the condition of having dry eyes. Symptoms include dryness in the eye, irritation, redness, discharge, blurred vision, and easily fatigued eyes. Symptoms range from mild and occasional to severe and continuous. Dry eye syndrome can lead to blurred vision, instability of the tear film, increased risk of damage to the ocular surface such as scarring of the cornea, and changes in the eye including the neurosensory system.

<span class="mw-page-title-main">Meloxicam</span> Nonsteroidal anti-inflammatory drug (NSAID)

Meloxicam, sold under the brand name Mobic among others, is a nonsteroidal anti-inflammatory medication (NSAID) used to treat pain and inflammation in rheumatic diseases and osteoarthritis. It is used by mouth or by injection into a vein. It is recommended that it be used for as short a period as possible and at a low dose.

<span class="mw-page-title-main">Ketorolac</span> Nonsteroidal anti-inflammatory drug (NSAID; analgesic)

Ketorolac, sold under the brand names Toradol, and Biorolac among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain. Specifically it is recommended for moderate to severe pain. Recommended duration of treatment is less than six days, and in Switzerland not more than two days. It is used by mouth, by nose, by injection into a vein or muscle, and as eye drops. Effects begin within an hour and last for up to eight hours.

<span class="mw-page-title-main">Latanoprost</span> Chemical compound

Latanoprost, sold under the brand name Xalatan among others, is a medication used to treat increased pressure inside the eye. This includes ocular hypertension and open-angle glaucoma. Latanaprost is applied as eye drops to the eyes. Onset of effects is usually within four hours, and they last for up to a day.

<span class="mw-page-title-main">Artificial tears</span> Eye drops for relieving dryness and irritation in the eye

Artificial tears are lubricating eye drops used to relieve dryness and irritation of the ocular surface. Dry eye syndrome is a common ocular surface disorder and is characterized by disruption of the tear film and increased inflammation.

<span class="mw-page-title-main">Corneal cross-linking</span> Surgical procedure

Corneal cross-linking (CXL) with riboflavin (vitamin B2) and UV-A light is a surgical treatment for corneal ectasia such as keratoconus, PMD, and post-LASIK ectasia.

Dorzolamide/timolol, sold under the brand name Cosopt among others, is a medication used to treat high pressure inside the eye including glaucoma. It is a combination of dorzolamide hydrochloride and timolol maleate. It may be used when a beta blocker, like timolol, is not sufficient alone. It is used as an eye drop.

<span class="mw-page-title-main">Brimonidine</span> Chemical compound

Brimonidine is an α2 agonist medication used to treat open-angle glaucoma, ocular hypertension, and rosacea. In rosacea it improves the redness. It is used as eye drops or applied to the skin.

<span class="mw-page-title-main">Sulfacetamide</span> Sulfonamide antibiotic

Sulfacetamide is a sulfonamide antibiotic.

<span class="mw-page-title-main">Brinzolamide</span> Chemical compound

Brinzolamide is a carbonic anhydrase inhibitor used to lower intraocular pressure in patients with open-angle glaucoma or ocular hypertension.

<span class="mw-page-title-main">Dorzolamide</span> Chemical compound

Dorzolamide, sold under the brand name Trusopt among others, is a medication used to treat high pressure inside the eye, including in cases of glaucoma. It is used as an eye drop. Effects begin within three hours and last for at least eight hours. It is also available as the combination dorzolamide/timolol.

<span class="mw-page-title-main">Bimatoprost</span> Chemical compound

Bimatoprost, sold under the brand name Lumigan among others, is a medication used to treat high pressure inside the eye including glaucoma. Specifically it is used for open angle glaucoma when other agents are not sufficient. It may also be used to increase the size of the eyelashes. It is used as an eye drop and effects generally occur within four hours.

<span class="mw-page-title-main">Nepafenac</span> NSAID analgesic and anti-inflammatory drug

Nepafenac, sold under the brand name Nevanac among others, is a nonsteroidal anti-inflammatory drug (NSAID), usually sold as a prescription eye drop 0.1% solution (Nevanac) or 0.3% solution (Ilevro). It is used to treat pain and inflammation associated with cataract surgery. Nepafenac is a prodrug of amfenac, an inhibitor of COX-1 and COX-2 activity.

<span class="mw-page-title-main">Tafluprost</span> Chemical compound

Tafluprost is a prostaglandin analogue. It is used topically to control the progression of open-angle glaucoma and in the management of ocular hypertension, alone or in combination with other medication. It reduces intraocular pressure by increasing the outflow of aqueous fluid from the eyes.

<span class="mw-page-title-main">Besifloxacin</span> Chemical compound

Besifloxacin (INN/USAN) is a fourth-generation fluoroquinolone antibiotic. The marketed compound is besifloxacin hydrochloride. It was developed by SSP Co. Ltd., Japan, and designated SS734. SSP licensed U.S. and European rights to SS734 for ophthalmic use to InSite Vision Incorporated in 2000. InSite Vision developed an eye drop formulation (ISV-403) and conducted preliminary clinical trials before selling the product and all rights to Bausch & Lomb in 2003.

<span class="mw-page-title-main">Phacolytic glaucoma</span> Medical condition

Phacolytic glaucoma (PG) is a form of glaucoma which is caused due to a leaking mature or immature cataract. Inflammatory glaucoma which occurs in phacolysis is a condition which is a result of the leakage of protein within the lens into the capsule of a mature or hyper mature cataract and involves a simple procedure to be cured that is referred to as cataract extraction.

<span class="mw-page-title-main">Intravitreal injection</span> Method of administration of drugs into the eye by injection with a fine needle

Intravitreal injection is the method of administration of drugs into the eye by injection with a fine needle. The medication will be directly applied into the vitreous humor. It is used to treat various eye diseases, such as age-related macular degeneration (AMD), diabetic retinopathy, and infections inside the eye such as endophthalmitis. As compared to topical administration, this method is beneficial for a more localized delivery of medications to the targeted site, as the needle can directly pass through the anatomical eye barrier and dynamic barrier. It could also minimize adverse drug effects on other body tissues via the systemic circulation, which could be a possible risk for intravenous injection of medications. Although there are risks of infections or other complications, with suitable precautions throughout the injection process, chances for these complications could be lowered.

References

  1. ↑ Rovere G, Nadal-Nicolás FM, Sobrado-Calvo P, García-Bernal D, Villegas-Pérez MP, Vidal-Sanz M, Agudo-Barriuso M (November 2016). "Topical Treatment With Bromfenac Reduces Retinal Gliosis and Inflammation After Optic Nerve Crush". Investigative Ophthalmology & Visual Science. 57 (14): 6098–6106. doi: 10.1167/iovs.16-20425 . PMID   27832276.
  2. ↑ "Bromfenac Sodium Monograph for Professionals". Drugs.com. 21 April 2020. Retrieved 23 November 2020.
  3. 1 2 3 4 5 6 Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.
  4. ↑ "Yellox EPAR". European Medicines Agency (EMA). 17 September 2018. Retrieved 23 November 2020.
  5. ↑ "Prolensa- bromfenac sodium solution/ drops". DailyMed. 1 March 2020. Retrieved 23 November 2020.
  6. 1 2 Sheppard JD (2016). "Topical bromfenac for prevention and treatment of cystoid macular edema following cataract surgery: a review". Clinical Ophthalmology. 10: 2099–2111. doi: 10.2147/OPTH.S86971 . PMC   5087782 . PMID   27822006.
  7. 1 2 3 4 5 6 7 8 9 "Yellox Summary of Product Characteristics" (PDF). European Medicines Agency. 11 January 2016.
  8. ↑ Schechter, BA (2019). "Use of topical bromfenac for treating ocular pain and inflammation beyond cataract surgery: a review of published studies". Clin Ophthalmol. 13: 1439–1460. doi: 10.2147/OPTH.S208700 . PMC   6682171 . PMID   31534309.
  9. ↑ Dinnendahl V, Fricke U, eds. (2012). Arzneistoff-Profile (in German). Vol. 2 (26 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN   978-3-7741-9846-3.
  10. ↑ "Ethical Products for Medical Professionals". Senju Pharmaceutical. Archived from the original on 20 December 2016. Retrieved 11 December 2016.
  11. 1 2 FDA Professional Drug Information for Xibrom.
  12. ↑ Hunter EB, Johnston PE, Tanner G, Pinson CW, Awad JA (August 1999). "Bromfenac (Duract)-associated hepatic failure requiring liver transplantation". The American Journal of Gastroenterology. 94 (8): 2299–301. doi:10.1111/j.1572-0241.1999.01321.x. PMID   10445569. S2CID   33021811.
  13. ↑ "Duract (bromfenac) Information". FDA . Retrieved 11 December 2016.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.