Ebastine | CAS#90729-43-4 | H1 antihistamine

MedKoo Cat#: 317143 | Name: Ebastine

Description:

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

Ebastine, is a H1 antihistamine with low potential for causing drowsiness. It does not penetrate the blood–brain barrier to a significant amount and thus combines an effective block of the H1 receptor in peripheral tissue with a low incidence of central side effects, i.e. seldom causing sedation or drowsiness. After oral administration, ebastine undergoes extensive first-pass metabolism by hepatic cytochrome P450 3A4 into its active carboxylic acid metabolite, carebastine. This conversion is practically complete. Ebastine is a second-generation H1 receptor antagonist that is indicated mainly for allergic rhinitis and chronic idiopathic urticaria.

Chemical Structure

Ebastine

CAS#90729-43-4

Theoretical Analysis

MedKoo Cat#: 317143

Name: Ebastine

CAS#: 90729-43-4

Chemical Formula: C32H39NO2

Exact Mass: 469.2981

Molecular Weight: 469.67

Elemental Analysis: C, 81.83; H, 8.37; N, 2.98; O, 6.81

Price and Availability

Size	Price	Availability
250mg	USD 250.00	2 Weeks
1g	USD 650.00	2 Weeks
5g	USD 1,450.00	2 weeks

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Related CAS #

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Synonym

RP64305; RP-64305; RP 64305; LAS W-090; LAS W090; LAS W 090; Ebastine; Brand name: Evastin; Kestine; Ebastel; Aleva; Ebatrol; Bactil; Busidril; Ebastel; Evastel; Kestin; Kestine.

IUPAC/Chemical Name

4-(4-(benzhydryloxy)piperidin-1-yl)-1-(4-(tert-butyl)phenyl)butan-1-one

InChi Key

MJJALKDDGIKVBE-UHFFFAOYSA-N

InChi Code

InChI=1S/C32H39NO2/c1-32(2,3)28-18-16-25(17-19-28)30(34)15-10-22-33-23-20-29(21-24-33)35-31(26-11-6-4-7-12-26)27-13-8-5-9-14-27/h4-9,11-14,16-19,29,31H,10,15,20-24H2,1-3H3

SMILES Code

O=C(CCCN1CCC(OC(C2=CC=CC=C2)C3=CC=CC=C3)CC1)C4=CC=C(C(C)(C)C)C=C4

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ebastine (LAS-W 090) is an orally active, second-generation histamine H1 receptor antagonist.

In vitro activity:

To further investigate whether ebastine can reduce EZH2 in other cancer cells, this study treated prostate cancer cells (DU145, VCaP), small cell lung cancer (H146, H82, H526), and lymphoma (L1236, Jeko-1, HDLM2) with ebastine at various concentrations. As shown in Fig. 1B and Fig. S1B, ebastine dose-dependently reduces the protein level of EZH2 and H3K27me3 in these cancer cell lines. Reference: Mol Cancer Ther. 2020 Oct; 19(10): 2023–2033. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7541747/

In vivo activity:

As shown in Fig. 4A, ebastine treatment significantly and dose-dependently reduced tumor growth and progression as indicated by tumor weight. Kaplan-Meier survival plot indicated that a higher dose of ebastine enhanced the survival of TNBC-PDX mice (Fig. 4B). Similarly, ebastine treatment reduced tumor growth and progression in SUM159 xenograft mice, as indicated by tumor volume (Fig. 4C) and tumor weight (Fig. 4D). More importantly, immunoblot analysis using tumor lysate from the ebastine-treated and control mice showed that EZH2 protein levels were decreased in vivo upon ebastine treatment (Fig. 4E). No significant change in body weight of these mice was observed among different treatments (Fig. S7A-B). Reference: Mol Cancer Ther. 2020 Oct; 19(10): 2023–2033. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7541747/

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	53.23
	Ethanol	51.3	109.12

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 469.67 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:

1. Li Q, Liu KY, Liu Q, Wang G, Jiang W, Meng Q, Yi Y, Yang Y, Wang R, Zhu S, Li C, Wu L, Zhao D, Yan L, Zhang L, Kim JS, Zu X, Kozielski AJ, Qian W, Chang JC, Patnaik A, Chen K, Cao Q. Antihistamine Drug Ebastine Inhibits Cancer Growth by Targeting Polycomb Group Protein EZH2. Mol Cancer Ther. 2020 Oct;19(10):2023-2033. doi: 10.1158/1535-7163.MCT-20-0250. Epub 2020 Aug 27. PMID: 32855270; PMCID: PMC7541747.

In vitro protocol:

In vivo protocol:

1: Jung HS, Park CH, Park YT, Bae MA, Lee YI, Kang BJ, Jegal Y, Ahn JJ, Lee T. Gynecomastia induced by H1-antihistamine (ebastine) in a patient with idiopathic anaphylaxis. Asia Pac Allergy. 2015 Jul;5(3):187-90. doi: 10.5415/apallergy.2015.5.3.187. Epub 2015 Jul 29. PubMed PMID: 26240797; PubMed Central PMCID: PMC4521169. 2: Rapolu R, Pandey AK, Raju ChK, Ghosh K, Srinivas K, Awasthi A, Navalgund SG, Surendranath KV. A novel UV degradation product of Ebastine: isolation and characterization using Q-TOF, NMR, IR and computational chemistry. J Pharm Biomed Anal. 2015 Mar 25;107:488-94. doi: 10.1016/j.jpba.2015.01.039. Epub 2015 Jan 29. PubMed PMID: 25679093. 3: Ibrahim FA, Wahba ME. Orthogonal projection to latent structures combined with artificial neural networks in non-destructive analysis of ebastine powder. Acta Chim Slov. 2014;61(1):11-8. PubMed PMID: 24664321. 4: Rana NS, Rajesh KS, Patel NN, Patel PR, Limbachiya U, Pasha TY. Development and Validation of RP-HPLC Method for the Simultaneous Estimation of Montelukast Sodium and Ebastine in Tablet Dosage Form. Indian J Pharm Sci. 2013 Sep;75(5):599-602. PubMed PMID: 24403662; PubMed Central PMCID: PMC3877523. 5: Schmidt AH, Molnár I. Using an innovative Quality-by-Design approach for development of a stability indicating UHPLC method for ebastine in the API and pharmaceutical formulations. J Pharm Biomed Anal. 2013 May 5;78-79:65-74. doi: 10.1016/j.jpba.2013.01.032. Epub 2013 Jan 31. PubMed PMID: 23454599. 6: Haggag RS, Belal TS. Gradient HPLC-DAD determination of two pharmaceutical mixtures containing the antihistaminic drug ebastine. J Chromatogr Sci. 2012 Nov-Dec;50(10):862-8. doi: 10.1093/chromsci/bms082. Epub 2012 Jun 7. PubMed PMID: 22677488. 7: Godse KV. Ebastine in chronic spontaneous urticaria in higher doses. Indian J Dermatol. 2011 Sep-Oct;56(5):597-8. doi: 10.4103/0019-5154.87168. PubMed PMID: 22121291; PubMed Central PMCID: PMC3221236. 8: Ibrahim F, Sharaf El-Din MK, Eid MI, Wahba ME. Validated stability indicating liquid chromatographic determination of ebastine in pharmaceuticals after pre column derivatization: Application to tablets and content uniformity testing. Chem Cent J. 2011 May 9;5:24. doi: 10.1186/1752-153X-5-24. PubMed PMID: 21554731; PubMed Central PMCID: PMC3113337. 9: Kang W, Elitzer S, Noh K, Bednarek T, Weiss M. Myocardial pharmacokinetics of ebastine, a substrate for cytochrome P450 2J, in rat isolated heart. Br J Pharmacol. 2011 Aug;163(8):1733-9. doi: 10.1111/j.1476-5381.2011.01338.x. PubMed PMID: 21410688; PubMed Central PMCID: PMC3166699. 10: Ibrahim F, El-Din MK, Eid MI, Wahba ME. Validated stability-indicating spectrofluorimetric methods for the determination of ebastine in pharmaceutical preparations. Chem Cent J. 2011 Mar 8;5(1):11. doi: 10.1186/1752-153X-5-11. PubMed PMID: 21385439; PubMed Central PMCID: PMC3061886. 11: Ciprandi G. Clinical utility and patient adherence with ebastine for allergic rhinitis. Patient Prefer Adherence. 2010 Oct 14;4:389-95. doi: 10.2147/PPA.S8186. PubMed PMID: 21206514; PubMed Central PMCID: PMC3003605. 12: Ohyama M, Shimizu A, Tanaka K, Amagai M. Experimental evaluation of ebastine, a second-generation anti-histamine, as a supportive medication for alopecia areata. J Dermatol Sci. 2010 May;58(2):154-7. doi: 10.1016/j.jdermsci.2010.03.009. Epub 2010 Mar 23. PubMed PMID: 20388588. 13: Shon JH, Yeo CW, Liu KH, Lee SS, Cha IJ, Shin JG. Itraconazole and rifampin alter significantly the disposition and antihistamine effect of ebastine and its metabolites in healthy participants. J Clin Pharmacol. 2010 Feb;50(2):195-204. doi: 10.1177/0091270009348974. Epub 2009 Oct 19. PubMed PMID: 19841159. 14: Aguilar D, Arias A, Báez C, González S, Hernández D, Linares FJ, López A, Macías A, Martínez A, Martínez HM, Martínez N, Mogica MD, Paz D, Rojo I, Sánchez A. [Multicenter study of satisfaction with fast-dissolving ebastine, 20 mg/ day, in Mexican patients with allergic rhinitis]. Rev Alerg Mex. 2009 Mar-Apr;56(2):36-40. Spanish. PubMed PMID: 19526952. 15: Magerl M, Schmolke J, Metz M, Zuberbier T, Siebenhaar F, Maurer M. Prevention of signs and symptoms of dermographic urticaria by single-dose ebastine 20 mg. Clin Exp Dermatol. 2009 Jul;34(5):e137-40. doi: 10.1111/j.1365-2230.2008.03097.x. Epub 2009 Mar 23. PubMed PMID: 19323664. 16: Ciprandi G, Cirillo I, Pistorio A, Di Gioacchino M, Fenoglio D. Ebastine increases IFN-gamma production in patients with persistent allergic rhinitis. J Biol Regul Homeost Agents. 2009 Jan-Mar;23(1):31-6. PubMed PMID: 19321044. 17: Tsiskarishvili NV, Dundua MM, Tsiskarishvili NI. [Avene-50 and Ebastine in treatment and prevention of photodermatosis]. Georgian Med News. 2009 Feb;(167):52-6. Russian. PubMed PMID: 19276471. 18: Rico S, Antonijoan R, Barbanoj M. Ebastine in the light of CONGA recommendations for the development of third-generation antihistamines. J Asthma Allergy. 2009 Aug 31;2:73-92. PubMed PMID: 21437146; PubMed Central PMCID: PMC3048600. 19: Sastre J. Ebastine in allergic rhinitis and chronic idiopathic urticaria. Allergy. 2008 Dec;63 Suppl 89:1-20. doi: 10.1111/j.1398-9995.2008.01897.x. Review. PubMed PMID: 19032340. 20: Roger A, Fortea J, Mora S, Artés M. Patient assessment of onset of action and overall satisfaction with ebastine fast-dissolving tablets in allergic rhinitis. Expert Rev Pharmacoecon Outcomes Res. 2008 Aug;8(4):337-42. doi: 10.1586/14737167.8.4.337. PubMed PMID: 20528340.