Emedastine

Names

[ Name ]:
Emedastine

[Synonym ]:
Emedastine
1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)-1H-benzo[d]imidazole
Emadine
Emedastina [INN-Spanish]
AL 3432A
Emedastina
1-methyl-4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane
1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)benzimidazole
1-(2-Ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)-1H-benzimidazole
emedastinum [INN_la]
Rapimine
1-(2-Ethoxyethyl)-2-(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)-1H-benzimidazole
1-[2-(Ethoxy)ethyl]-2-(4-methyl-1-homopiperazinyl)benzimidazole
Emedastine [INN]
Emedastinum
1H-Benzimidazole, 1-(2-ethoxyethyl)-2-(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)-
UNII-9J1H7Y9OJV
MFCD00865647
Emedastinum [INN-Latin]

Biological Activity

[Description]:

Emedastine is an orally active, selective and high affinity histamine H1 receptor antagonist with a Ki value of 1.3 nM. Emedastine is a benzimidazole derivative with potent antiallergic properties and used for allergic rhinitis, allergic skin diseases and allergic conjunctivitis[1][2][3].

[Related Catalog]:

Signaling Pathways >> Immunology/Inflammation >> Histamine Receptor

Research Areas >> Inflammation/Immunology

Signaling Pathways >> GPCR/G Protein >> Histamine Receptor

[Target]

H1 Receptor:1.3 nM (Ki)

H2 Receptor:49067 nM (Ki)

H3 Receptor:12430 nM (Ki)

[In Vitro]

Emedastine inhibits histamine H2 receptor (Ki=49067 nM) and histamine H3 receptor (Ki=12430 nM)[1]. High concentrations of Emedastine (1 and 10 ng/ml) significantly inhibits type 1 collagen production in normal human dermal fibroblasts[2]. Emedastine (1, 10, 100, 1000 nM) at concentrations of ≥ 10 nM inhibits CC chemokine-elicited eosinophil migration[2].

[In Vivo]

Emedastine (0.03, 0.1, 0.3 mg/kg; orally; pretreatment of 30 min) significantly suppresses histamine-induced scratching with 0.1 and 0.3 mg/kg but not 0.03 mg/kg[3]. Pretreatment with Emedastine (0.03, 0.1, 0.3 mg/kg; orally) significantly inhibits the scratching induced by substance P and leukotriene B[3]. Emedastine (0.3 mg/kg, p.o.) produces significant inhibition of passive peritoneal anaphylaxis in guinea-pigs[2]. Emedastine inhibits histamine-induced contractions of isolated ileum (IC50=6.1 nM)[2]. Animal Model: Male ICR mice 5-6 weeks of age[3] Dosage: 0.03, 0.1, 0.3 mg/kg Administration: Orally; 30 min before pruritogen injection Result: Significantly suppressed histamine-induced scratching with pretreatment of 0.1 and 0.3 mg/kg.

[References]

[1]. Sharif NA, et al. Emedastine: a potent, high affinity histamine H1-receptor-selective antagonist for ocular use: receptor binding and second messenger studies. J Ocul Pharmacol. 1994 Winter;10(4):653-64.

[2]. Murota H, et al. Emedastine difumarate: a review of its potential ameliorating effect for tissue remodeling in allergic diseases. Expert Opin Pharmacother. 2009 Aug;10(11):1859-67.

[3]. Andoh T, et al. Involvement of blockade of leukotriene B(4) action in anti-pruritic effects of emedastine in mice. Eur J Pharmacol. 2000 Oct 6;406(1):149-52.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
446.6±55.0 °C at 760 mmHg

[ Melting Point ]:
148-151ºC

[ Molecular Formula ]:
C₁₇H₂₆N₄O

[ Molecular Weight ]:
302.414

[ Flash Point ]:
223.9±31.5 °C

[ Exact Mass ]:
302.210663

[ PSA ]:
33.53000

[ LogP ]:
3.02

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.595

[ Storage condition ]:
-20℃

Safety Information

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%