100981-43-9

Basic information

• Product Name: Ebrotidine
• Synonyms: Ebrotidine;FI 3542;FI3542;FI-3542;Ulsanic;(E)-N-[[[2-[[[2-[(Aminoiminomethyl)amino]-4-thiazolyl]methyl]thio]ethyl]amino]methylene]-4-bromobenzenesulfonamide
• CAS NO: 100981-43-9
• Molecular Formula: C₁₄H₁₇BrN₆O₂S₃
• Molecular Weight: 477.43
• Mol File: 100981-43-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 142.5-146℃
• Boiling Point: 672.3 °C at 760 mmHg
• Flash Point: 360.4 °C
• Appearance: /
• Density: 1.73 g/cm³
• Vapor Pressure: 6.2E-18mmHg at 25°C
• Refractive Index: 1.739
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 5.25±0.40(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: Ebrotidine(CAS DataBase Reference)
• NIST Chemistry Reference: Ebrotidine(100981-43-9)
• EPA Substance Registry System: Ebrotidine(100981-43-9)

Safety Data

• Hazardous Substances Data: 100981-43-9(Hazardous Substances Data)

Usage

Description

Ebrocit was launched in Spain as a gastroprotective agent. It was prepared from 4-bromobenzenesulfonamide in two steps. Ebrocit's activity arises from its ability to antagonize histamine H2-receptors (the first of a new generation) showing 1.5-2.5 times higher affinity than Ranitidine and 2-fold greater affinity than cimetidine which correlates to an antisecretory potency of 1 times and 4-10 times respectively. Cytoand gastroprotection arises from increased gastric mucus production, enhanced physiochemical properties (decreased permeability of H+), and an increase in mucin glycosylation and sulfation. It acts on gastric mucosal EGF and PDGF receptor expression. Nitric oxide was also found to be involved. Ebrocit caused enhanced mucosal blood flow with anti H.pylori activity. It has diminished P450 binding which eliminates the possibility of mutagenic nitrosoamine formation.

Originator

Ferrer (Spain)

Uses

Ebrotidine is a H2 receptor antagonist that has shown gastroprotective properties against gastric mucosal damange.

Brand name

Ebrocit

references

[1]. patel s s, wilde m i. ebrotidine. drugs, 1996, 51(6): 974-80; discussion 981.[2]. romero a, gómez f, villamayor f, et al. study of the population of enterochromaffin-like cells in mouse gastric mucosa after long-term treatment with ebrotidine. toxicologic pathology, 1996, 24(2): 160-165.

InChI:InChI=1/C14H17BrN6O2S3/c15-10-1-3-12(4-2-10)26(22,23)19-9-18-5-6-24-7-11-8-25-14(20-11)21-13(16)17/h1-4,8-9H,5-7H2,(H,18,19)(H4,16,17,20,21)

Upstream product

• 100981-68-8 ethyl 4-bromobenzenesulfonyl formimidate 
• 100981-43-9 ebrotidine 
• 71916-66-0 2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine 
• 701-34-8 4-bromo-benzenesulfonic acid amide 
• 81152-53-6 94/2007B 
• 69014-10-4 2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine dihydrochloride 

Downstream Products

• 701-34-8 4-bromo-benzenesulfonic acid amide 

Related news

Determination of Ebrotidine (cas 100981-43-9) and its metabolites by capillary electrophoresis with UV and mass spectrometry detection08/24/2019

This study describes the application of capillary electrophoresis (CE) to the analysis of ebrotidine and its metabolites as an alternative analytical technique to liquid chromatography. Comparison between UV–diode array spectroscopy and mass spectrometry (MS) using an ion-trap system with elect...detailed

General paperEffect of Ebrotidine (cas 100981-43-9) on the synthesis and secretion of gastric sulfomucin08/23/2019

1.1. The effect of a new antiulcer agent, ebrotidine, on the synthesis and secretion of sulfomucin in gastric mucosa was investigated. Rat gastric mucosal segments were incubated in DMEM containing [3H]proline, [3H]glucosamine and [35S]Na2SO4 as markers for mucin synthesis, glycosylation and sul...detailed

General paperEnhancement in the protective qualities of gastric mucus by Ebrotidine (cas 100981-43-9) during duodenal ulcer healing08/21/2019

1.1. Gastric mucus from duodenal ulcer patients before and following therapy with a new antiulcer agent, ebrotidine, at 400, 600 and 800 mg dose was examined for changes in the physicochemical qualities and anti-H. pylori activity.2.2. The results of physical measurements revealed that successfu...detailed

Determination of Ebrotidine (cas 100981-43-9) and its metabolites in human urine by reversed-phase ion-pair high-performance liquid chromatography08/20/2019

Ebrotidine is a new H2-receptor antagonist with powerful antisecretory activity, demonstrated gastroprotection and the ability to inhibit protease and lipase activities of Helicobacter pylori. As a tool in the clinical pharmacokinetic study of ebrotidine, an analytical method for the simultaneou...detailed

Ebrotidine (cas 100981-43-9) effect on the proteolytic and lipolytic activities of Helicobacter pylori08/19/2019

1.1. The effect of ebrotidine, a new antiulcer agent, on the activity of mucus degrading of protease and lipase enzymes elaborated by Helicobacter pylori was investigated.2.2. In the absence of ebrotidine, the H. pylori protease caused extensive degradation of gastric mucus protein, while free f...detailed

Determination of Ebrotidine (cas 100981-43-9) and its metabolites by micellar electrokinetic capillary chromatography08/15/2019

Ebrotidine and its potential metabolites were determined by micellar electrokinetic capillary chromatography (MECC) using sodium dodecylsulfate (SDS) as surfactant. The influences of buffer composition, SDS concentration and addition of a neutral surfactant such as Brij 35 were studied. A 40 mM ...detailed

Relevant articles and documents

Metabolites of ebrotidine, a new H2-receptor antagonist, in human urine

Ebrotidine is a new H2-receptor antagonist which exhibits a remarkable ability for gastric mucosal protection. A preliminary metabolic pathway for this compound was proposed and the hypothetic metabolites were synthesized. The presence of ebrot

Synthesis and assessment of formamidines as new histamine H2-receptor antagonists

Four series of compounds whose substructure contains a formamidine functionalized as a novel group in the chemistry of histamine H2-receptors have been synthesized. Series design, synthesis and pharmacological data including inhibition of histamine-stimulated acid secretion, inhibition of acid secretion p.o. and pA2 are reported. N-[(E)-[[2- [[[2[(Diaminomethylene)amino]-4- thiazolyl]methyl]thio]ethyl]amino]methylene]-4-bromo-benzenesu llfonamide (ebrotidine, CAS 100981-43-9, FI-3542) was selected for further research.

SULFONAMIDINES, PROCESS FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME

Sulfonamidine is disclosed of the general formula (I): EQU1 wherein R is a group selected from 2-(5-methyl-1H-imidazole-4-yl) methyl!thio!ethyl!, 2-5-(dimethylamino)methyl!-2-furanyl!methyl!thio!ethyl, 2-2-(aminoiminomethyl)amino!-4-thiazolyl!methyl!thio!ethyl! or 3-3-(1-piperidinylmethyl)phenoxy! propyl and R 1 is alkyl; or a phenyl group optionally substituted by alkyl, halogen, nitro, alkoxy, alkanoylamino, carboxylic acid, alkoxycarbonyl, dialkylamino, alkylsulphonyl, alkylsulphonylamino or alkylthio; or 1,3,4-thiadiazole-2-yl substituted by alkanoylamino, and the pharmaceutically acceptable salts thereof, as well as a process for preparing these compounds and pharmaceutical compositions containing the same. These compounds have antiulcer activity and can be used in the treatment of peptic ulcers and other pathologies caused or stimulated by gastric acidity.