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EMEDASTINE FUMARATE

Product Name
EMEDASTINE FUMARATE
CAS No.
87233-62-3
Chemical Name
EMEDASTINE FUMARATE
Synonyms
Emadine;1-(2-ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)benzimidazoledifumarate;Daren;kb2413;Remicut;kb-2413;kg-2413;Rapimine;AL 3432A;ly188695
CBNumber
CB6714475
Molecular Formula
C25H34N4O9
Formula Weight
534.56
MOL File
87233-62-3.mol
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EMEDASTINE FUMARATE Property

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

RTECS 
DD8870000
HS Code 
2933992600
Toxicity
LD50 orally in guinea pigs: 744 mg/kg (Fukuda)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0000537
Product name
Emedastine difumarate
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
y0000537
Price
$150
Updated
2024/03/01
Sigma-Aldrich
Product number
1234806
Product name
Emedastine difumarate
Packaging
100mg
Price
$406
Updated
2024/03/01
TCI Chemical
Product number
E0936
Product name
Emedastine Difumarate
Purity
>98.0%(HPLC)(T)
Packaging
200mg
Price
$244
Updated
2021/12/16
Cayman Chemical
Product number
23946
Product name
Emedastine (fumarate)
Purity
≥98%
Packaging
5mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
23946
Product name
Emedastine (fumarate)
Purity
≥98%
Packaging
10mg
Price
$61
Updated
2024/03/01
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EMEDASTINE FUMARATE Chemical Properties,Usage,Production

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.

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.

Chemical Properties

White or yellowish powder

Originator

Kanebo (Japan)

Uses

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.

EMEDASTINE FUMARATE Preparation Products And Raw materials

Raw materials

Preparation Products

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EMEDASTINE FUMARATE Suppliers

China 112 Europe 1 France 1 India 5 South Korea 1 United Kingdom 1 United States 15 Global 136
BOC Sciences
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United States
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Aladdin Scientific
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View Lastest Price from EMEDASTINE FUMARATE manufacturers

Henan Fengda Chemical Co., Ltd
Product
EMEDASTINE FUMARATE 87233-62-3
Price
US $32.00-1.30/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2024-04-15
Baoji Guokang Healthchem co.,ltd
Product
EMEDASTINE FUMARATE 87233-62-3
Price
US $150.00/g
Min. Order
1g
Purity
99%
Supply Ability
100KG
Release date
2021-06-03
Hebei Zhanyao Biotechnology Co. Ltd
Product
EMEDASTINE FUMARATE 87233-62-3
Price
US $10.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
99%
Supply Ability
20 Tons
Release date
2021-11-22

87233-62-3, EMEDASTINE FUMARATERelated Search:

/ EmedastineN-Oxide Emedastine EP Impurity C HCl EMEDASTINE FUMARATE Emedastine

  • 1-(2-ethoxyethyl)-2-(4-methyl-1-homopiperazinyl)benzimidazoledifumarate
  • 1-(2-ethoxyethyl)-2-(4-methylhexahydro-1h-1,4-diazepin-1-yl)-benzimidazol
  • 1-(2-ethoxyethyl)-2-(4-methylhexahydro-1h-1,4-diazepin-1-yl)benzimidazolefum
  • 1-(2-Ethoxyethyl)-2-(4-methylhexahydro-1H-1,4-diazepine-1-yl)-1H-benzimidazole·bisfumaric acid
  • Daren
  • Emedastin difumarate
  • Emedastin fumarate
  • Remicut
  • Emedastine Difumarate (100 mg)
  • Rapimine
  • Emadine
  • AL 3432A
  • 1-(2-Ethoxyethyl)-2-(hexahydro-4-methyl-1H-1,4-diazepin-1-yl)-1H-benzimidazole (2E)-2-butenedioate (1:2)
  • 1-(2-ethoxyethyl)-2-(4-methyl-1,4-diazepan-1-yl)-1H-benzo[d]imidazole difumarate
  • 1h-benzimidazole,1-(2-ethoxyethyl)-2-(hexahydro-4-methyl-1h-1,4-diazepin-1-yl)
  • arate(1:2)
  • emedastinedifumarate
  • kb2413
  • kb-2413
  • kg-2413
  • ly188695
  • EMEDASTINE FUMARATE
  • EmedastineDifumarate&gt
  • Emedastine difumarate CRS
  • 1-(2-Ethoxyethyl)-2-(4-methylhexahydro-1H-1,4-diazepin-1- yl)-1H-benzimidazole bis[hydrogen (2E)-butenedioate
  • Emestine Fumarate
  • Emedastine Difumarate (1234806)
  • Fmedastine Difumarate
  • 87233-62-3
  • C25H34N4O9
  • C17H26N4O2C4H4O4