{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 451556318 | IUPAC_name = ''N''-(4-bromophenyl)sulfonyl-''N<nowiki>'</nowiki>''-[2-<nowiki>[[</nowiki>2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]ethyl]methanimidamide | image = Ebrotidine.svg | image_class = skin-invert-image | width = 270
<!--Clinical data--> | tradename = | routes_of_administration = Oral
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 100981-43-9 | PubChem = 65869 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 59279 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1742471 | smiles = Brc1ccc(cc1)S(=O)(=O)N/C=N/CCSCc2csc(n2)N=C(N)N | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/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) | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = ZQHFZHPUZXNPMF-UHFFFAOYSA-N | UNII_Ref = {{fdacite|correct|FDA}} | UNII = TMZ3IBW2OW
<!--Chemical data--> | C=14 | H=17 | Br=1 | N=6 | O=2 | S=3 }}
'''Ebrotidine''' is an H<sub>2</sub> receptor antagonist with gastroprotective activity against ethanol-, aspirin- or stress-induced gastric mucosal damage.<ref name = Patel>{{cite journal | vauthors = Patel SS, Wilde MI | title = Ebrotidine | journal = Drugs | volume = 51 | issue = 6 | pages = 974–80; discussion 981 | date = June 1996 | pmid = 8736619 | doi = 10.2165/00003495-199651060-00006 | s2cid = 264001739 }}</ref> The antisecretory properties of ebrotidine are similar to those of ranitidine, and approximately 10-fold greater than those of cimetidine. Ebrotidine has anti-''Helicobacter pylori'' activity via inhibition of the urease enzyme and the proteolytic and mucolytic activities of the bacterium. However, its activity is synergistic with a number of antibacterial agents. Ebrotidine counteracts the inhibitory effects of ''H. pylori'' lipopolysaccharides. Ebrotidine was withdrawn from the market due to risks of hepatotoxicity.
Ebrotidine has been shown to be as effective as ranitidine for the treatment of gastric or duodenal ulcers or erosive reflux oesophagitis, with significantly better ulcer healing rates (albeit inexplicably) in those who smoke.<ref name = Patel />
== References == {{Reflist}}
{{Histaminergics}}
Category:Amidines Category:Guanidines Category:H2 receptor antagonists Category:Hepatotoxins Category:4-Bromophenyl compounds Category:Sulfonamides Category:Thiazoles Category:Thioethers
{{gastrointestinal-drug-stub}}