Emedastine Difumerate

• CAT Number: R043027
• CAS Number: 87233-62-3
• Molecular Formula: C25H34N4O9
• Molecular Weight: 534.566
• Purity: ≥95%
• Synonyms: 1H-1,4-Diazepine 1H-Benzimidazole deriv. Difumerate; 1-Methyl-4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane Difumerate
• Target: Histamine H1 Receptor Antagonist
• Storage: -20°C
• IUPAC Name: (E)-but-2-enedioic acid;1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)benzimidazole
• InChI: InChI=1S/C17H26N4O.2C4H4O4/c1-3-22-14-13-21-16-8-5-4-7-15(16)18-17(21)20-10-6-9-19(2)11-12-20;2*5-3(6)1-2-4(7)8/h4-5,7-8H,3,6,9-14H2,1-2H3;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1+
• InChIKey: FWLKKPKZQYVAFR-LVEZLNDCSA-N
• SMILES: CCOCCN1C2=CC=CC=C2N=C1N3CCCN(CC3)C.C(=CC(=O)O)C(=O)O.C(=CC(=O)O)C(=O)O

Emedastine Difumarate is the difumarate salt form of emedastine, a second generation, selective histamine H1 receptor antagonist with anti-allergic activity. This medication is an antihistamine, prescribed for allergic conjunctivitis. It blocks histamine/’s action, which reduces allergy symptoms. Emedastine reversibly and competitively blocks histamine by binding to H1 receptors, thus blocking its downstream activity. As a result, this agent interferes with mediator release from mast cells either by inhibiting calcium ion influx across mast cell/basophil plasma membrane or by inhibiting intracellular calcium ion release within the cells. Upon ocular administration, emedastine causes a dose-dependent inhibition of histamine-stimulated vascular permeability in the conjunctiva.

Reference

1: Murota H, Katayama I. Emedastine difumarate: a review of its potential ameliorating effect for tissue remodeling in allergic diseases. Expert Opin Pharmacother. 2009 Aug;10(11):1859-67. doi: 10.1517/14656560903078410. Review. PubMed PMID: 19558341.2: Tian Y, Zhang Z, Liang J, Li W, Chen Y. High-performance liquid chromatography-electrospray ionization-mass spectrometric determination of emedastine difumarate in human plasma and its pharmacokinetics. J Chromatogr Sci. 2007 Mar;45(3):158-64. PubMed PMID: 17462131.3: Pons-Guiraud A, Nekam K, Lahovsky J, Costa A, Piacentini A. Emedastine difumarate versus loratadine in chronic idiopathic urticaria: a randomized, double-blind, controlled European multicentre clinical trial. Eur J Dermatol. 2006 Nov-Dec;16(6):649-54. PubMed PMID: 17229605.4: Corrado ME, Radicioni MM, Hartwig J, Assandri A, Oldeman HG, Mion A. Clinical study of the therapeutic efficacy and safety of emedastine difumarate versus terfenadine in the treatment of seasonal allergic rhinitis. Arzneimittelforschung. 2004;54(10):660-5. PubMed PMID: 15553105.5: Brunner M, Kletter K, Assandri A, Ermanno Corrado M, Eichler HG, Müller M. Pharmacokinetic and mass balance study of unlabelled and (14)C-labelled emedastine difumarate in healthy volunteers. Xenobiotica. 2002 Sep;32(9):761-70. PubMed PMID: 12396273.6: D/’Arienzo PA, Leonardi A, Bensch G. Randomized, double-masked, placebo-controlled comparison of the efficacy of emedastine difumarate 0.05% ophthalmic solution and ketotifen fumarate 0.025% ophthalmic solution in the human conjunctival allergen challenge model. Clin Ther. 2002 Mar;24(3):409-16. PubMed PMID: 11952024.7: Joukhadar C, Herranz U, Pernerstorfer T, Assandri A, Klein N, Schrolnberger C, Lackner E, Eichler HG, Müller M. Pharmacokinetics of emedastine difumarate, a new anti-histaminic agent in patients with renal impairment. Eur J Clin Pharmacol. 2001 Mar;56(12):905-10. PubMed PMID: 11317479.8: Okubo K, Pawankar R, Gotoh M, Yagi T. Adhesive explant culture of allergic nasal mucosa: effect of emedastine difumarate, an anti-allergic drug. Jpn J Pharmacol. 1999 Mar;79(3):351-7. PubMed PMID: 10230864.9: Hamada T, Kawashima T, Awata N. [Selective and sensitive determination of an antiallergic agent, emedastine difumarate (KG-2413), in human plasma by the radioreceptor assay combined with a high-performance liquid chromatography]. Yakugaku Zasshi. 1989 Oct;109(10):749-54. Japanese. PubMed PMID: 2576060.10: Murota H, Bae S, Hamasaki Y, Maruyama R, Katayama I. Emedastine difumarate inhibits histamine-induced collagen synthesis in dermal fibroblasts. J Investig Allergol Clin Immunol. 2008;18(4):245-52. Erratum in: J Investig Allergol Clin Immunol. 2009;19(2):166. Dosage error in article text. PubMed PMID: 18714531.11: Horak F, Stübner P, Zieglmayer R, Kavina A, Corrado ME, Assandri A, Mion A. Clinical study of the therapeutic efficacy and safety of emedastine difumarate versus cetirizine in the treatment of seasonal allergic rhinitis. Arzneimittelforschung. 2004;54(10):666-72. PubMed PMID: 15553106.12: Saito H, Yamamoto N, Tomita S, Taniguchi M, Hasegawa M, Akiyama K, Kawaguchi H, Takahashi K. Effect of emedastine difumarate on CC chemokine-elicited eosinophil migration. Int Arch Allergy Immunol. 2001;125 Suppl 1:22-8. PubMed PMID: 11408768.13: Secchi A, Leonardi A, Discepola M, Deschenes J, Abelson MB. An efficacy and tolerance comparison of emedastine difumarate 0.05% and levocabastine hydrochloride 0.05%: reducing chemosis and eyelid swelling in subjects with seasonal allergic conjunctivitis. Emadine Study Group. Acta Ophthalmol Scand Suppl. 2000;(230):48-51. PubMed PMID: 11057351.14: el-Shazly AE, Masuyama K, Samejima Y, Eura M, Ishikawa T. Inhibition of human eosinophil chemotaxis in vitro by the anti-allergic agent emedastine difumarate. Immunopharmacol Immunotoxicol. 1996 Nov;18(4):587-95. PubMed PMID: 8933171.15: Saito T, Hagihara A, Igarashi N, Matsuda N, Yamashita A, Ito K, Mio M, Tasaka K. Inhibitory effects of emedastine difumarate on histamine release. Jpn J Pharmacol. 1993 Jun;62(2):137-43. PubMed PMID: 7690432.16: Sakai T, Awata N, Watanabe J. Hepatic transport of an antiallergic agent, emedastine difumarate: interspecies difference in rats and guinea pigs. Chem Pharm Bull (Tokyo). 1990 May;38(5):1349-52. PubMed PMID: 2393961.17: Wada Y, Hamada T, Kawashima T, Awata N. [In vitro metabolism of an antiallergic agent, emedastine difumarate, in rats and guinea pigs]. Yakugaku Zasshi. 1990 Jan;110(1):40-8. Japanese. PubMed PMID: 1972410.