WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H326713
CAS#: 190786-44-8 (besylate)
Description: Bepotastine is a non-sedating, selective antagonist of the histamine 1 (H1) receptor. Bepotastine was approved in Japan for use in the treatment of allergic rhinitis and uriticaria/puritus in July 2000 and January 2002, respectively, and is marketed by Tanabe Seiyaku Co., Ltd. under the brand name Talion. It is available in oral and opthalmic dosage forms in Japan. The opthalmic solution is FDA approved since Sept 8, 2009 and is under the brand name Bepreve.
Hodoodo Cat#: H326713
Name: Bepotastine besylate
CAS#: 190786-44-8 (besylate)
Chemical Formula: C27H31ClN2O6S
Exact Mass: 0.00
Molecular Weight: 547.063
Elemental Analysis: C, 59.28; H, 5.71; Cl, 6.48; N, 5.12; O, 17.55; S, 5.86
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Related CAS #: 125602-71-3 (free base) 190786-44-8 (besylate) 1160415-45-1 (tosylate)
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
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).
HS Tariff Code: 2934.99.9001
More Info: 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
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The following data is based on the product molecular weight 547.06 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.
| 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Yoon S, Jin BH, Kim CO, Park K, Park MS, Chae D. Pharmacokinetic Modeling of Bepotastine for Determination of Optimal Dosage Regimen in Pediatric Patients with Allergic Rhinitis or Urticaria. Pharmaceutics. 2024 Feb 27;16(3):334. doi: 10.3390/pharmaceutics16030334. PMID: 38543228; PMCID: PMC10975960.
2: Kitahiro Y, Yamamoto K, Yakushijin K, Ioroi T, Tanda M, Itohara K, Omura T, Minami H, Yano I. The Efficacy of Bepotastine Besilate Compared With Hydroxyzine Pamoate for Preventing Infusion Reactions to the First Dose of Rituximab in Patients With Non-Hodgkin Lymphoma: Protocol for a Phase II, Double-Blind, Multicenter Randomized Trial. JMIR Res Protoc. 2024 Feb 22;13:e54882. doi: 10.2196/54882. PMID: 38386393; PMCID: PMC10921330.
3: Marini MC, Berra ML, Girado F, Albera PA, Del Papa MS, Passerini MS, Aguilar AJ. Efficacy and Toxicity Evaluation of Bepotastine Besilate 1.5% Preservative- Free Eye Drops Vs Olopatadine Hydrochloride 0.2% Bak-Preserved Eye Drops in Patients with Allergic Conjunctivitis. Clin Ophthalmol. 2023 Nov 16;17:3477-3489. doi: 10.2147/OPTH.S431889. PMID: 38026598; PMCID: PMC10658941.
4: Lee JH, Oh JY, Kwon HS, Kim TB, Cho YS, Song WJ. Effects of bepotastine, a nonsedating H1-antihistamine, for the treatment of persistent cough and allergic rhinitis: a randomised, double-blind, placebo-controlled trial. ERJ Open Res. 2023 Oct 2;9(5):00448-2023. doi: 10.1183/23120541.00448-2023. PMID: 37868148; PMCID: PMC10588790.
5: Kim MJ, Kulkarni V, Goode MA, Sivesind TE. Exploring the interactions of antihistamine with retinoic acid receptor beta (RARB) by molecular dynamics simulations and genome-wide meta-analysis. J Mol Graph Model. 2023 Nov;124:108539. doi: 10.1016/j.jmgm.2023.108539. Epub 2023 Jun 9. PMID: 37331258; PMCID: PMC10529808.
6: Gayathri E, Sowmya P, Punnagai K, Mahalakshmi V. Comparative study on the efficacy and safety of bepotastine besilate versus levocetirizine in chronic spontaneous urticaria: A randomised, open-label, parallel study. Indian J Dermatol Venereol Leprol. 2023 Sep-Oct;89(5):672-679. doi: 10.25259/IJDVL_333_2021. PMID: 37067147.
7: Jin P, Li X, Xia Y, Li H, Li X, Yang ZY, Wang Z, Xu C, Fang T, Zhou D, Xiong X, Wang SY, Xu S, Gao Q. Bepotastine Sensitizes Ovarian Cancer to PARP Inhibitors through Suppressing NF-κB-Triggered SASP in Cancer-Associated Fibroblasts. Mol Cancer Ther. 2023 Apr 3;22(4):447-458. doi: 10.1158/1535-7163.MCT-22-0396. PMID: 36780236.
8: Shamil KS, Prakruti PP, Anuradha MG, Bela JS, Chetna KD. Old versus new antihistamines: Effects on cognition and psychomotor functions. J Family Med Prim Care. 2022 Oct;11(10):5909-5917. doi: 10.4103/jfmpc.jfmpc_77_22. Epub 2022 Oct 31. PMID: 36618177; PMCID: PMC9810909.
9: Gumieniczek A, Lejwoda K, Data N. Chemical Stability Study of H1 Antihistaminic Drugs from the First and the Second Generations, Diphenhydramine, Azelastine and Bepotastine, in Pure APIs and in the Presence of Two Excipients, Citric Acid and Polyvinyl Alcohol. Molecules. 2022 Nov 29;27(23):8322. doi: 10.3390/molecules27238322. PMID: 36500415; PMCID: PMC9735860.
10: Sil A, Rahaman S, Mondal N, Ahmed SS, Tarafdar D, Patra AC, Roy S, Das NK. An Investigator-Blind Randomized Controlled Trial Comparing Effectiveness, Safety of Levocetirizine and Bepotastine in Chronic Urticaria. Indian J Dermatol. 2021 Sep-Oct;66(5):472-478. doi: 10.4103/ijd.ijd_813_20. PMID: 35068500; PMCID: PMC8751697.
11: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Bepotastine. 2021 Sep 20. PMID: 30000754.
12: Wu K, Yan J, Wang X, Yin X, Shi G, Yang L, Li F, Huang J, Shao L. Efficient synthesis of bepotastine and cloperastine intermediates using engineered alcohol dehydrogenase with a hydrophobic pocket. Appl Microbiol Biotechnol. 2021 Aug;105(14-15):5873-5882. doi: 10.1007/s00253-021-11413-9. Epub 2021 Aug 3. PMID: 34342711.
13: Won TB, Kim HG, Kim JW, Kim JK, Kim YH, Kim SW, Kim HY, Kim DW, Kim SW, Kim CH, Rhee CS. Efficacy and safety of rupatadine fumarate in the treatment of perennial allergic rhinitis: A multicenter, double-blinded, randomized, placebo- controlled, bridging study in Koreans. Asian Pac J Allergy Immunol. 2021 Jul 11. doi: 10.12932/AP-201220-1019. Epub ahead of print. PMID: 34246214.
14: Kang MS, Lee J, Park SH, Yu HS, Lee JE. Development of allergic conjunctivitis induced by Acanthamoeba excretory-secretory protein and the effect of resolvin D1 on treatment. Curr Eye Res. 2021 Dec;46(12):1792-1799. doi: 10.1080/02713683.2021.1934878. Epub 2021 Jul 26. PMID: 34029500.
15: Drugs for allergic rhinitis and allergic conjunctivitis. Med Lett Drugs Ther. 2021 Apr 19;63(1622):57-64. PMID: 33848281.
16: Sruthi V, Reddy RN, Sowmini K, Grace NS. To evaluate the efficacy and safety of olopatadine 0.1% ophthalmic solution and bepotastine 1.5% ophthalmic solution in patients with vernal keratoconjunctivitis in a tertiary care hospital. Indian J Pharmacol. 2020 Nov-Dec;52(6):476-481. doi: 10.4103/ijp.IJP_174_20. PMID: 33666188; PMCID: PMC8092179.
17: Ayyappanavar S, Sridhar S, Kumar K, Jayanthi CR, Gangasagara SB, Rathod BLS, Preethi B, Mittal P. Comparative analysis of safety and efficacy of Alcaftadine 0.25%, Olopatadine hydrochloride 0.2% and Bepotastine besilate 1.5% in allergic conjunctivitis. Indian J Ophthalmol. 2021 Feb;69(2):257-261. doi: 10.4103/ijo.IJO_2083_20. PMID: 33463568; PMCID: PMC7933849.
18: Mo JH, Jeong JH, Kim TH, Kim ST, Kim SW, Lee KH, Hong SN, Kim HY, Kim DW, Kim DY, Kim CH, Cho SH, Rhee CS. Double-Blind Placebo-Controlled Trial of Bepotastine Salicylate in Patients With Allergic Rhinitis. Laryngoscope. 2021 Mar;131(3):E702-E709. doi: 10.1002/lary.28906. Epub 2020 Jul 31. PMID: 32735704.
19: Singh DK, Sahu A, Wani AA, Bharatam PV, Chakraborti AK, Giri S, Singh S. Characterization of Photodegradation Products of Bepotastine Besilate and In Silico Evaluation of Their Physicochemical, Absorption, Distribution, Metabolism, Excretion and Toxicity Properties. J Pharm Sci. 2020 Jun;109(6):1883-1895. doi: 10.1016/j.xphs.2020.03.004. Epub 2020 Mar 12. PMID: 32173321.
20: Kim SI, Park CY, Fordjuor G, Lee JH, Lee JS, Lee JE. Comparison of cytotoxicities and anti-allergic effects of topical ocular dual-action anti- allergic agents. BMC Ophthalmol. 2019 Nov 8;19(1):217. doi: 10.1186/s12886-019-1228-5. PMID: 31703568; PMCID: PMC6839072.
