Bepotastine besylate

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

MedKoo CAT#: 326713

CAS#: 190786-44-8 (besylate)

Description: Bepotastine, also known as TAU-284, is a 2nd generation antihistamine (H1-receptor antagonist). It was approved in Japan for use in the treatment of allergic rhinitis and urticaria/pruritus in July 2000 and January 2002, respectively.


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Bepotastine besylate, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326713
Name: Bepotastine besylate
CAS#: 190786-44-8 (besylate)
Chemical Formula: C27H31ClN2O6S
Exact Mass:
Molecular Weight: 547.063
Elemental Analysis: C, 59.28; H, 5.71; Cl, 6.48; N, 5.12; O, 17.55; S, 5.86


Synonym: TAU-284; TAU 284; TAU284; Bepotastine besylate; bepotastine besilate; Bepreve; Talion.

IUPAC/Chemical Name: (S)-4-(4-((4-chlorophenyl)(pyridin-2-yl)methoxy)piperidin-1-yl)butanoic acid compound with benzenesulfonic acid (1:1)

InChi Key: UDGHXQPQKQPSBB-BOXHHOBZSA-N

InChi Code: InChI=1S/C21H25ClN2O3.C6H6O3S/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;7-10(8,9)6-4-2-1-3-5-6/h1-2,4,6-9,12,18,21H,3,5,10-11,13-15H2,(H,25,26);1-5H,(H,7,8,9)/t21-;/m0./s1

SMILES Code: OC(CCCN1CCC(O[C@H](c2ncccc2)c3ccc(Cl)cc3)CC1)=O.OS(=O)(c4ccccc4)=O


Technical Data

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).

Harmonized System Code:
293490


Additional Information

Related:
190786-44-8 (Bepotastine besylate)
125602-71-3 (Bepotastine free).

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. The ophthalmic formulation has shown minimal systemic absorption, between 1 and 1.5% in healthy adults


References

1: Okubo K, Ichimura M, Koyama T, Susuta Y, Izaki H. Double-blind placebo-controlled study of bepotastine besilate in pediatric patients with perennial allergic rhinitis. Expert Opin Pharmacother. 2015;16(16):2395-408. doi: 10.1517/14656566.2015.1085511. Epub 2015 Sep 12. PubMed PMID: 26364765.

2: Lim DS, Youn YS, Kwack SJ, Kwak HM, Lim SK, Kim JY, Um YM, Lee JD, Hyeon JH, Kim YJ, Kim HS, Lee BM. Comparative efficacy and bioequivalence of novel h1-antihistamine bepotastine salts (nicotinate and salicylate). J Toxicol Environ Health A. 2014;77(22-24):1451-66. doi: 10.1080/15287394.2014.955833. PubMed PMID: 25343294.

3: Bergmann MT, Williams JI, Gomes PJ. Treatment of allergic conjunctivitis with bepotastine besilate ophthalmic solution 1.5%. Clin Ophthalmol. 2014 Aug 13;8:1495-505. doi: 10.2147/OPTH.S66637. eCollection 2014. PubMed PMID: 25152611; PubMed Central PMCID: PMC4140238.

4: Shentu J, Zhou H, Hu X, Wu G, Wu L, Zhu M, Zhai Y, Zheng Y, Liu J. Comparative fasting bioavailability of 2 bepotastine formulations in healthy male Chinese volunteers: an open-label, randomized, single-dose, 2-way crossover study. Clin Ther. 2014 Apr 1;36(4):579-85. doi: 10.1016/j.clinthera.2014.02.020. Epub 2014 Mar 18. PubMed PMID: 24656153.

5: Bielory L, Duttachoudhury S, McMunn A. Bepotastine besilate for the treatment of pruritus. Expert Opin Pharmacother. 2013 Dec;14(18):2553-69. doi: 10.1517/14656566.2013.849242. Epub 2013 Nov 5. Review. PubMed PMID: 24191914.

6: Kim KA, Park JY. Pharmacokinetic comparisons of bepotastine besilate and bepotastine salicylate in healthy subjects. Clin Drug Investig. 2013 Dec;33(12):913-9. doi: 10.1007/s40261-013-0140-7. PubMed PMID: 24105252.

7: Choi YK, Chung YH, Nam YS, Kang da Y, Kim H, Lee SE, Kim HR, Lee YS, Jeong JH. UPLC-MS/MS method for determination of bepotastine in human plasma. J Chromatogr Sci. 2014 Sep;52(8):886-93. doi: 10.1093/chromsci/bmt135. Epub 2013 Sep 10. PubMed PMID: 24023058.

8: Carr WW, Nayak AS, Ratner PH, Gow JA, McNamara TR, Williams JI; Bepotastine Besilate Ophthalmic Solution 1.5% (Bepreve) Study Group. Efficacy of bepotastine besilate ophthalmic solution 1.5% for seasonal allergic conjunctivitis: a randomized, placebo-controlled, natural exposure, clinical trial. Allergy Asthma Proc. 2013 May-Jun;34(3):247-54. PubMed PMID: 23484763.

9: McCabe CF, McCabe SE. Comparative efficacy of bepotastine besilate 1.5% ophthalmic solution versus olopatadine hydrochloride 0.2% ophthalmic solution evaluated by patient preference. Clin Ophthalmol. 2012;6:1731-8. doi: 10.2147/OPTH.S35431. Epub 2012 Oct 29. PubMed PMID: 23152650; PubMed Central PMCID: PMC3497448.

10: Meier EJ, Torkildsen GL, Gow JA, McNamara TR, Gomes PJ, Williams JI; Bepotastine Besilate Ophthalmic Solutions Study Group. Integrated phase III trials of bepotastine besilate ophthalmic solution 1.5% for ocular itching associated with allergic conjunctivitis. Allergy Asthma Proc. 2012 May-Jun;33(3):265-74. PubMed PMID: 22991696.

11: Cho KH, Choi HG. Development of novel bepotastine salicylate salt bioequivalent to the commercial bepotastine besilate in beagle dogs. Drug Dev Ind Pharm. 2013 Jun;39(6):901-8. doi: 10.3109/03639045.2012.717295. Epub 2012 Sep 10. PubMed PMID: 22963365.

12: Tanizaki H, Ikoma A, Fukuoka M, Miyachi Y, Kabashima K. Effects of bepotastine and fexofenadine on histamine-induced flare, wheal and itch. Int Arch Allergy Immunol. 2012;158(2):191-5. doi: 10.1159/000330663. Epub 2012 Jan 26. PubMed PMID: 22286689.

13: Kawakami T, Kimura S, Haga T, Doi R, Kyoya M, Nakagawa K, Soma Y. Health-related quality of life assessed by the effect of bepotastine besilate in patients with pruritus: importance of emotions score in atopic dermatitis. J Dermatol. 2012 Jun;39(6):527-30. doi: 10.1111/j.1346-8138.2011.01418.x. Epub 2011 Oct 31. PubMed PMID: 22035542.

14: Williams JI, Kennedy KS, Gow JA, Torkildsen GL, Abelson MB, Gomes PJ, McNamara TR; Bepotastine Besilate Ophthalmic Solutions Study Group. Prolonged effectiveness of bepotastine besilate ophthalmic solution for the treatment of ocular symptoms of allergic conjunctivitis. J Ocul Pharmacol Ther. 2011 Aug;27(4):385-93. doi: 10.1089/jop.2011.0005. Epub 2011 Jun 7. PubMed PMID: 21649522.

15: Wingard JB, Mah FS. Critical appraisal of bepotastine in the treatment of ocular itching associated with allergic conjunctivitis. Clin Ophthalmol. 2011;5:201-7. doi: 10.2147/OPTH.S8665. Epub 2011 Feb 15. PubMed PMID: 21386912; PubMed Central PMCID: PMC3046989.

16: Williams JI, Gow JA, Klier SM, McCue SL, Salapatek AM, McNamara TR. Non-clinical pharmacology, pharmacokinetics, and safety findings for the antihistamine bepotastine besilate. Curr Med Res Opin. 2010 Oct;26(10):2329-38. doi: 10.1185/03007995.2010.486753. Review. PubMed PMID: 20735291.

17: Lyseng-Williamson KA. Oral bepotastine: in allergic disorders. Drugs. 2010 Aug 20;70(12):1579-91. doi: 10.2165/11205880-000000000-00000. Review. Erratum in: Drugs. 2011 Apr 16;71(6):756. PubMed PMID: 20687621.

18: Torkildsen GL, Williams JI, Gow JA, Gomes PJ, Abelson MB, McNamara TR; Bepotastine Besilate Ophthalmic Solutions Clinical Study Group. Bepotastine besilate ophthalmic solution for the relief of nonocular symptoms provoked by conjunctival allergen challenge. Ann Allergy Asthma Immunol. 2010 Jul;105(1):57-64. doi: 10.1016/j.anai.2010.04.005. PubMed PMID: 20642205.

19: Macejko TT, Bergmann MT, Williams JI, Gow JA, Gomes PJ, McNamara TR, Abelson MB; Bepotastine Besilate Ophthalmic Solutions Clinical Study Group. Multicenter clinical evaluation of bepotastine besilate ophthalmic solutions 1.0% and 1.5% to treat allergic conjunctivitis. Am J Ophthalmol. 2010 Jul;150(1):122-127.e5. doi: 10.1016/j.ajo.2010.02.007. Epub 2010 May 20. PubMed PMID: 20488431.

20: Kida T, Fujii A, Sakai O, Iemura M, Atsumi I, Wada T, Sakaki H. Bepotastine besilate, a highly selective histamine H(1) receptor antagonist, suppresses vascular hyperpermeability and eosinophil recruitment in in vitro and in vivo experimental allergic conjunctivitis models. Exp Eye Res. 2010 Jul;91(1):85-91. doi: 10.1016/j.exer.2010.04.006. Epub 2010 Apr 20. PubMed PMID: 20412793.