Bepotastine

Bepotastine
Names
Pronunciationbep oh tas' teen
Trade namesBepreve[1]
Other namesBepotastine besilate
IUPAC name
  • 4-[4-[(4-chlorophenyl)-pyridin-2-ylmethoxy]piperidin-1-yl]butanoic acid
Clinical data
Drug classAntihistamine, hay fever, hives[2][1]
Main usesAllergic conjunctivitis[1]
Side effectsEye irritation, headache, stuffy nose[3]
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Pregnancy
category
  • US: C (Risk not ruled out)
    Routes of
    use    		By mouth, eye drops
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa610012
    Legal
    Legal status
    • In general: ℞ (Prescription only)
    Pharmacokinetics
    BioavailabilityHigh (by mouth)
    Minimal (topical)
    Protein binding~55%
    ExcretionRenal (75–85
    Chemical and physical data
    FormulaC21H25ClN2O3
    Molar mass388.89 g·mol−1
    3D model (JSmol)
    SMILES
    • Clc1ccc(cc1)C(OC2CCN(CCCC(=O)O)CC2)c3ncccc3
    InChI
    • 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) checkY
    • Key:YWGDOWXRIALTES-UHFFFAOYSA-N checkY

    Bepotastine, sold under the brand names Bepreve among others, is a medication used as an eye drop to treat allergic conjunctivitis.[1] By mouth it may be used for allergic rhinitis (hay fever) and hives.[2]

    Common side effects eye irritation, headache, and stuffy nose.[3] While there is no evidence of harm in pregnancy, such use has not been well studied.[3][4] It is an antihistamine and mast cell stabilizer.[1]

    Bepotastine was approved for medical use in Japan in 2000 and the United States in 2009.[2][3] In the United States 5 ml for the eyes costs about 70 USD as of 2022.[5]

    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.[6] The ophthalmic formulation has shown minimal systemic absorption, between 1 and 1.5% in healthy adults.[7] Common side effects are eye irritation, headache, unpleasant taste, and nasopharyngitis.[7] The main route of elimination is urinary excretion, 75-90% excreted unchanged.[7]

    Society and culture

    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.[8] ISTA Pharmaceuticals was acquired by Bausch & Lomb in March 2012 for $500 million.[9] Bausch & Lomb hold the patent for bepotastine besilate (https://www.accessdata.fda.gov/scripts/cder/ob/docs/temptn.cfm Archived 2018-11-01 at the Wayback Machine. On November 26, 2014, Bausch & Lomb sued Micro Labs USA for patent infringement.[10] 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.[11]

    Research

    A Phase III clinical trial was carried out in 2010 to evaluate the effectiveness of bepotastine besilate ophthalmic solutions 1.0% and 1.5%.[12] 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 that typical use in humans.[7] Evidence of infertility was seen in rats at 33,000 times the typical ocular dose in humans.[7] 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.[7]

    References

    1. 1 2 3 4 5 "Bepotastine Monograph for Professionals". Drugs.com. Archived from the original on 27 October 2021. Retrieved 24 November 2021.
    2. 1 2 3 Leung, Donald Y. M.; Sampson, Hugh; Geha, Raif; Szefler, Stanley J. (13 October 2010). Pediatric Allergy: Principles and Practice E-Book. Elsevier Health Sciences. ISBN 978-1-4377-3778-3. Archived from the original on 11 January 2022. Retrieved 9 January 2022.
    3. 1 2 3 4 "DailyMed - BEPOTASTINE BESILATE solution/ drops". dailymed.nlm.nih.gov. Archived from the original on 11 January 2022. Retrieved 9 January 2022.
    4. ↑ "Bepotastine ophthalmic (Bepreve) Use During Pregnancy". Drugs.com. Archived from the original on 25 October 2021. Retrieved 9 January 2022.
    5. ↑ "Bepotastine Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 23 August 2016. Retrieved 9 January 2022.
    6. ↑ "Bepotastine Monograph". Lexicomp. Archived from the original on 2018-11-01. Retrieved 2021-08-04.
    7. 1 2 3 4 5 6 "Bepreve prescribing Information" (PDF). Archived (PDF) from the original on 2015-08-11. Retrieved 2021-08-04.
    8. ↑ "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. Archived from the original on October 5, 2018. Retrieved August 4, 2021.
    9. ↑ "Bausch & Lomb to Buy ISTA Pharmaceuticals for $500 Million". DealBook. Archived from the original on 2018-10-05. Retrieved 2015-12-05.
    10. ↑ "Bausch & Lomb Inc. et al. v. Micro Labs USA, Inc. et al". Patent Docs. JD Supra, LLC. December 8, 2014. Archived from the original on November 1, 2018. Retrieved August 4, 2021.
    11. ↑ 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.
    12. ↑ 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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