Bepotastine

Last updated
Bepotastine
Bepotastine.svg
Clinical data
Trade names Bepreve
AHFS/Drugs.com International Drug Names
MedlinePlus a610012
Routes of
administration 		Oral, eye drops
ATC code
  • none
Legal status
Legal status
  • CA: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability High (oral)
Minimal (topical)
Protein binding ~55%
Excretion Renal (75–85
Identifiers
  • 4-[4-[(4-chlorophenyl)-pyridin-2-ylmethoxy]piperidin-1-yl]butanoic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C21H25ClN2O3
Molar mass 388.89 g·mol−1
3D model (JSmol)
  • Clc1ccc(cc1)C(OC2CCN(CCCC(=O)O)CC2)c3ncccc3
  • InChI=1S/C21H25ClN2O3/c22-17-8-6-16(7-9-17)21(19-4-1-2-12-23-19)27-18-10-14-24(15-11-18)13-3-5-20(25)26/h1-2,4,6-9,12,18,21H,3,5,10-11,13-15H2,(H,25,26) Yes check.svgY
  • Key:YWGDOWXRIALTES-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Bepotastine (Talion, Bepreve) is a 2nd generation antihistamine. [1] It was approved in Japan for use in the treatment of allergic rhinitis and urticaria/pruritus in July 2000, and January 2002, respectively. It is marketed in the United States as an eye drop under the brand name Bepreve, by ISTA Pharmaceuticals, a subsidiary of Bausch + Lomb.[ citation needed ]

Contents

Pharmacology

Bepotastine is available as an ophthalmic solution and oral tablet. It is a direct H1-receptor antagonist that inhibits the release of histamine from mast cells. [2] The ophthalmic formulation has shown minimal systemic absorption, between 1 and 1.5% in healthy adults. [3] Common side effects are eye irritation, headache, unpleasant taste, and nasopharyngitis. [3] The main route of elimination is urinary excretion, 75-90% excreted unchanged. [3]

Marketing history

It is marketed in Japan by Tanabe Seiyaku under the brand name Talion. Talion was co-developed by Tanabe Seiyaku and Ube Industries, the latter of which discovered bepotastine. In 2001, Tanabe Seiyaku granted Senju, now owned by Allergan, exclusive worldwide rights, with the exception of certain Asian countries, to develop, manufacture and market bepotastine for ophthalmic use. Senju, in turn, has granted the United States rights for the ophthalmic preparation to ISTA Pharmaceuticals.

Sales and patents

In 2011, ISTA pharmaceuticals experienced a 2.4% increase in net revenues from 2010, which was driven by the sales of Bepreve. Their net revenue for 2011 was $160.3 million. [4] ISTA Pharmaceuticals was acquired by Bausch & Lomb in March 2012 for $500 million. [5] Bausch & Lomb hold the patent for bepotastine besilate (https://www.accessdata.fda.gov/scripts/cder/ob/docs/temptn.cfm. On November 26, 2014, Bausch & Lomb sued Micro Labs USA for patent infringement. [6] Bausch & Lomb was recently bought out by Valeant Pharmaceuticals in May 2013 for $8.57 billion, Valeant's largest acquisition to date, causing the company's stock to rise 25% when the deal was announced. [7]

Clinical trials

A Phase III clinical trial was carried out in 2010 to evaluate the effectiveness of bepotastine besilate ophthalmic solutions 1.0% and 1.5%. [8] These solutions were compared to a placebo and evaluated for their ability to reduce ocular itchiness. The study was carried out with 130 individuals and evaluated after 15 minutes, 8 hours, or 16 hours. There was a reduction in itchiness at all-time points for both ophthalmic solutions. The study concluded that bepotastine besilate ophthalmic formulations reduced ocular itchiness for at least 8 hours after dosing compared to placebo. Phase I and II trials were carried out in Japan.

Studies have been performed in animals and bepotastine besilate was not found to be teratogenic in rats during fetal development, even at 3,300 times more than typical use in humans. [3] Evidence of infertility was seen in rats at 33,000 times the typical ocular dose in humans. [3] The safety and efficacy has not been established in patients under 2 years of age and has been extrapolated from adults for patients under 10 years of age. [3]

Related Research Articles

<span class="mw-page-title-main">Bausch & Lomb</span> Canadian eye health company

Bausch + Lomb is an American-Canadian eye health products company based in Vaughan, Ontario, Canada. It is one of the world's largest suppliers of contact lenses, lens care products, pharmaceuticals, intraocular lenses, and other eye surgery products. The company was founded in Rochester, New York, in 1853 by optician John Bausch and cabinet maker turned financial backer Henry Lomb. Until its sale in 2013, Bausch + Lomb was one of the oldest continually operating companies in the United States.

<span class="mw-page-title-main">Fexofenadine</span> Antihistamine medication

Fexofenadine, sold under the brand name Allegra among others, is an antihistamine pharmaceutical drug used in the treatment of allergy symptoms, such as hay fever and urticaria.

<span class="mw-page-title-main">Allergic conjunctivitis</span> Medical condition

Allergic conjunctivitis (AC) is inflammation of the conjunctiva due to allergy. Although allergens differ among patients, the most common cause is hay fever. Symptoms consist of redness, edema (swelling) of the conjunctiva, itching, and increased lacrimation. If this is combined with rhinitis, the condition is termed allergic rhinoconjunctivitis (ARC).

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

Olopatadine, sold under the brand name Opatanol among others, is a medication used to decrease the symptoms of allergic conjunctivitis and allergic rhinitis. It is used as eye drops or as a nasal spray. The eye drops generally result in an improvement within half an hour.

Bausch Health Companies Inc. is an American-Canadian domiciled multinational specialty pharmaceutical company based in Laval, Quebec, Canada. It develops, manufactures and markets pharmaceutical products and branded generic drugs, primarily for skin diseases, gastrointestinal disorders, eye health and neurology. Bausch Health owns Bausch & Lomb, a supplier of eye health products.

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">Azelastine</span> Chemical compound

Azelastine, sold under the brand name Optivar among others, is a H1 receptor-blocking medication primarily used as a nasal spray to treat allergic rhinitis (hay fever) and as eye drops for allergic conjunctivitis. Other uses may include asthma and skin rashes for which it is taken by mouth. Onset of effects is within minutes when used in the eyes and within an hour when used in the nose. Effects last for up to 12 hours.

<span class="mw-page-title-main">Loteprednol</span> Pharmaceutical drug

Loteprednol is a topical corticosteroid used to treat inflammations of the eye. It is marketed by Bausch and Lomb as Lotemax and Loterex.

<span class="mw-page-title-main">Clocortolone</span> Pharmaceutical drug

Clocortolone (Cloderm) is a topical steroid. It is used in the form of an ester, clocortolone pivalate, and applied as a cream. It is used for the treatment of dermatitis and is considered a medium-strength corticosteroid. It is unusual among steroids in that it contains a chlorine atom and a fluorine atom.

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

Ebastine is a H1 antihistamine with low potential for causing drowsiness.

<span class="mw-page-title-main">NicOx</span>

Nicox S.A. is a French ophthalmology company developing treatments to maintain vision and improve ocular health. Nicox is headquartered in Sophia Antipolis, France, and its Chairman and CEO is Michele Garufi.

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

Bromfenac is a nonsteroidal 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. In the European Union, the brand name is Yellox. Bromfenac is indicated for the treatment of ocular inflammation and pain after cataract surgery.

<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">ISTA Pharmaceuticals</span> US-based pharmaceutical company

ISTA Pharmaceuticals, Inc, was a US-based pharmaceutical company that specialized in ophthalmic pharmaceutical products and discovers, develops, and markets therapies for inflammation, ocular pain, glaucoma, allergy, and dry eye. ISTA was acquired by Bausch & Lomb, an eye care company, on March 26, 2012. Under the deal, Bausch & Lomb have agreed to pay $9.10 per share for ISTA, bringing the total value of the acquisition to $500 million. In 2012, Valeant Pharmaceuticals withdrew its $360 million offer.

<span class="mw-page-title-main">Mapracorat</span> Type of selective glucocorticoid receptor agonist

Mapracorat is an anti-inflammatory drug belonging to the experimental class of selective glucocorticoid receptor agonists (SEGRAs). It is in clinical trials for the topical treatment of atopic dermatitis, inflammation following cataract surgery, and allergic conjunctivitis. Preliminary investigation for the treatment of keratoconjunctivitis sicca has been conducted in cellular models.

<span class="mw-page-title-main">Alimera Sciences</span>

Alimera Sciences, Inc. is a biopharmaceutical company based in Alpharetta, Georgia that specializes in the commercialization and development of prescription ophthalmic pharmaceuticals. The company's main focus is on diseases affecting the back of the eye, or retina. Its main product is Iluvien, a fluocinolone acetonide intravitreal implant.

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

Alcaftadine is used to prevent eye irritation brought on by allergic conjunctivitis. It is a H1 histamine receptor antagonist.

<span class="mw-page-title-main">Bilastine</span> Antihistamine medication

Bilastine is an antihistamine medication used to treat hives (urticaria), allergic rhinitis and itchy inflamed eyes (allergic conjunctivitis) caused by an allergy. It is a second-generation antihistamine and takes effect by selectively inhibiting the histamine H1 receptor, preventing these allergic reactions. Bilastine has an effectiveness similar to cetirizine, fexofenadine, and desloratadine.

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

Lifitegrast, sold under the brand name Xiidra, is a medication for the treatment of signs and symptoms of dry eye, a syndrome called keratoconjunctivitis sicca. Lifitegrast reduces inflammation by inhibiting inflammatory cell binding. It is often used in conjunction with ciclosporin for dry eye treatment including meibomian gland dysfunction and inflammatory dry eye.

References

  1. ↑ Takahashi H, Ishida-Yamamoto A, Iizuka H (September 2004). "Effects of bepotastine, cetirizine, fexofenadine, and olopatadine on histamine-induced wheal-and flare-response, sedation, and psychomotor performance". Clinical and Experimental Dermatology. 29 (5): 526–32. doi:10.1111/j.1365-2230.2004.01618.x. PMID   15347340. S2CID   9843760.
  2. ↑ "Bepotastine Monograph". Lexicomp.
  3. 1 2 3 4 5 6 "Bepreve prescribing Information" (PDF). Archived from the original (PDF) on 2015-08-11. Retrieved 2015-11-30.
  4. ↑ "2011 Net Revenues Increase to $160.3 Million On an Adjusted Cash Net Income Basis, ISTA Posts Second Year of Profitability Company Reaffirms 2012 Financial Guidance". Last 10K. February 23, 2012.
  5. ↑ "Bausch & Lomb to Buy ISTA Pharmaceuticals for $500 Million". DealBook. 26 March 2012. Retrieved 2015-12-05.
  6. ↑ "Bausch & Lomb Inc. et al. v. Micro Labs USA, Inc. et al". Patent Docs. JD Supra, LLC. December 8, 2014.
  7. ↑ Blackwell R, Silcoff S, Marotte B (27 May 2013). "Valenant pharmaceuticals eyes China with Bausch deal". The Globe and Mail. Archived from the original on 28 May 2013.
  8. ↑ Macejko TT, Bergmann MT, Williams JI, Gow JA, Gomes PJ, McNamara TR, Abelson MB (July 2010). "Multicenter clinical evaluation of bepotastine besilate ophthalmic solutions 1.0% and 1.5% to treat allergic conjunctivitis". American Journal of Ophthalmology. 150 (1): 122–127.e5. doi:10.1016/j.ajo.2010.02.007. PMID   20488431.
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