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HomeProduct name listEMEDASTINE FUMARATE

EMEDASTINE FUMARATE

  • CAS NO.:87233-62-3
  • Empirical Formula: C25H34N4O9
  • Molecular Weight: 534.56
  • MDL number: MFCD00923844
  • EINECS: 805-825-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-04-15 15:30:59
EMEDASTINE FUMARATE Structural

What is EMEDASTINE FUMARATE?

Description

Emedastine is a histamine H1 receptor antagonist (Ki = 1.3 nM). It is selective for histamine H1 over H2 and H3 receptors (Kis = 49 and 12.43 μM, respectively), as well as α1-, α2-, and β1-adrenergic and dopamine D1 and D2 receptors, and the serotonin (5-HT) receptor subtypes 5-HT1 and 5-HT2 at 10 μM. Emedastine inhibits histamine-induced phosphoinositide turnover and intracellular calcium mobilization in primary human conjunctival epithelial cells (HCECs; IC50s = 1.6 and 2.9 nM, respectively). It also inhibits histamine-stimulated secretion of IL-6, IL-8, and GM-CSF by primary HCECs (IC50s = 2.23, 3.42, and 1.50 nM, respectively). Ocular application of emedastine prior to histamine challenge inhibits vascular permeability in guinea pigs. Formulations containing emedastine have been used in the treatment of allergic conjunctivitis.

Description

Emedastine difumarate, a potent H1-receptor antagonist, was launched in Japan for the treatment of allergic rhinitis and urticaria. Emedastine exerts its antiallergic effect via inhibition of substance P-induced histamine release. It has been demonstrated both in vitro and in vivo that this effect is mediated by the inhibition of Ca2+release from extracellular stores and of Ca2+ influx into mast cells. In a clinical trial with bronchial asthma, emedastine improved asthmatic symptoms in 55.3% of patients.

Chemical properties

White or yellowish powder

Originator

Kanebo (Japan)

The Uses of EMEDASTINE FUMARATE

Antihistaminic, H1-receptor; asthma prophylactic; anti-allergic.

Definition

ChEBI: The fumaric acid salt of emedastine containing two molecules of fumaric acid for each molecule of emedastine. A relatively selective histamine H1 antagonist, it is used for allergic rhinitis, urticaria, and pruritic skin disorders, and in eyedrops for the symptomatic relief of allergic conjuntivitis.

Manufacturing Process

Preparation of 2-(4-methyl-1-piperazinyl)benzimidazole. A mixture of 2- chlorobenzimidazole (10.00 g) and N-mehylpiperazine (20.00 g) is stirred at 125°C for 5 hours. A 10% aqueous sodium hydroxide (100 ml) is added to the reaction mixture, and the precipitated crystals are separated by filtration. The filtrate is extracted with chloroform, and the chloroform extract is evaporated to dryness to give the same crystals. The crystals are combined and recrystallized from water-methanol to give 2-(4-methyl-1- piperazinyl)benzimidazole (7.02 g) as colorless needles, m.p. 225°-226°C.
2-(4-Methyl-1-piperazinyl)benzimididazole (5.00 g) prepared as above is dissolved in N,N-dimethylformamide (50 ml) and thereto is added sodium hydride (concentration: 50%) (1.50 g) at room temperature, and the mixture is stirred for 30 minutes. To the mixture is added 2-bromoethyl ethyl ether (4.00 g), and the mixture is stirred at 70°C for 10 hours. To the reaction mixture is added water (150 ml), and the mixture is extracted with ethyl acetate. The extract is washed with water, dried over anhydrous magnesium sulfate and then concentrated to give a brown oily substance (5.40 g). The brown oily substance is treated with fumaric acid (3.26 g) in hot ethanol. The crude crystals thus obtained are recrystallized from ethyl acetate-ethanol to give 1-[2-(ethoxy)ethyl]-2-(4-methyl-1-piperazinyl)benzimidazole 3/2 fumarate (6.31 g) as colorless plates, melting point 167.5°-168.5°C. Elementary analysis for C22H30N4O7: Calcd. (%): C, 57.13; H, 6.54; N, 12.11; Found (%): C, 57.04; H, 6.44; N, 12.02.
1-[2-(Ethoxy)ethyl]-2-(4-methyl-1-piperazinyl)benzimidazole can be prepared using 2-chloro-(1-[2-(ethoxy)ethyl]benzimidazole), (last one can be produced from 2-bromoethyl ethyl ether 2-chlorobenzimidazole) and N-methylpiperazine and fumaric acid there are obtained crude crystals, which are recrystallized from ethanol to give 1-[2-(ethoxy)ethyl]-2-(4-methyl-1- piperazinyl)benzimidazole 3/2 fumarate. This product has the same physical properties as those of the product above described.

brand name

Emadine (Alcon);Daren;Remicut.

Therapeutic Function

Antiallergic, Antihistaminic

Hazard

A poison by ingestion.

Properties of EMEDASTINE FUMARATE

Melting point: 148-151°
storage temp.  2-8°C
solubility  Soluble in water, sparingly soluble in anhydrous ethanol, very slightly soluble in acetone.
form  neat
Merck  14,3557

Safety information for EMEDASTINE FUMARATE

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P501:Dispose of contents/container to..…

Computed Descriptors for EMEDASTINE FUMARATE

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