Ebrotidine

Base Information

• Chemical Name: Ebrotidine
• CAS No.: 100981-43-9
• Molecular Formula: C14H17BrN6O2S3
• Molecular Weight: 477.43
• Hs Code.: 2942000000
• UNII: TMZ3IBW2OW
• DSSTox Substance ID: DTXSID80143601
• Nikkaji Number: J494.271J
• Wikipedia: Ebrotidine
• Wikidata: Q5332065
• NCI Thesaurus Code: C77440
• Pharos Ligand ID: QXMRP38S4FBU
• Metabolomics Workbench ID: 49600
• ChEMBL ID: CHEMBL1742471
• Mol file: 100981-43-9.mol

Synonyms:4-bromo-N-(((2-(((-((diaminomethylene)amino)-4-thiazolyl)methyl)thio)ethyl)amino)methylene)benzenesulfonamide;ebrotidine

Chemical Property of Ebrotidine

Chemical Property:

• Vapor Pressure: 6.2E-18mmHg at 25°C
• Melting Point: 142.5-146℃
• Refractive Index: 1.739
• Boiling Point: 672.3 °C at 760 mmHg
• PKA: 5.25±0.40(Predicted)
• Flash Point: 360.4 °C
• PSA: 195.24000
• Density: 1.73 g/cm³
• LogP: 4.79570
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 475.97585
• Heavy Atom Count: 26
• Complexity: 586

Purity/Quality:

99% ^*data from raw suppliers

Ebrotidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1S(=O)(=O)NC=NCCSCC2=CSC(=N2)N=C(N)N)Br
• 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.
• Uses: Ebrotidine is a H2 receptor antagonist that has shown gastroprotective properties against gastric mucosal damange.

Technology Process of Ebrotidine

There total 11 articles about Ebrotidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 59.0%

ethyl 4-bromobenzenesulfonyl formimidate (100981-68-8) + 2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine dihydrochloride (69014-10-4,71916-64-8) → ebrotidine (100981-43-9)

Guidance literature:

With potassium hydroxide; In methanol; for 2h; Ambient temperature;

DOI:10.1016/0223-5234(88)90174-2

Reference yield: 59.0%

ethyl 4-bromobenzenesulfonyl formimidate (100981-68-8) + 2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine (71916-66-0) → ebrotidine (100981-43-9)

Guidance literature:

In methanol; for 2h; Ambient temperature;

DOI:10.1002/jps.2600830228

Reference yield:

ebrotidine (100981-43-9,765244-65-3) → Ebrocit (100981-43-9)

Guidance literature:

In methanol;

upstream raw materials:

ethyl 4-bromobenzenesulfonyl formimidate

2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine

2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine dihydrochloride

94/2007B

Downstream raw materials:

4-bromo-benzenesulfonic acid amide

Refernces

• 1、 -. "Forms A and B of N-[[[2-[[[2-[(diaminomethylene)amino]-4-thiazolyl]methyl ]thio]ethyl]ami no]methylene]-4-bromo-benzenesulfonamide". . . Retrieved 2008/06/13.
• 2、 Anglada,Marquez,Sacristan,Ortiz. "Inhibitors of gastric acid secretion: N-sulphonyl formamidines in a series of new histamine H2-receptor antagonists". . p. 97 - 100. Retrieved 2007/10/02.