Ebrotidine

Ebrotidine is an H₂ receptor antagonist with gastroprotective activity against ethanol-, aspirin- or stress-induced gastric mucosal damage.^[1] 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 Ebrotidine was withdrawn from the market due to risks of hepatotoxicity.

Quick Facts Clinical data, Routes ofadministration ...

Ebrotidine

Clinical data
Routes of administration	Oral
Identifiers
IUPAC name N-(4-bromophenyl)sulfonyl-N'-[2-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]ethyl]methanimidamide
CAS Number	100981-43-9 Y
PubChem CID	65869
ChemSpider	59279 N
UNII	TMZ3IBW2OW
ChEMBL	ChEMBL1742471 N
CompTox Dashboard (EPA)	DTXSID80143601
Chemical and physical data
Formula	C14H17BrN6O2S3
Molar mass	477.41 g·mol−1
3D model (JSmol)	Interactive image
SMILES Brc1ccc(cc1)S(=O)(=O)N/C=N/CCSCc2csc(n2)N=C(N)N
InChI InChI=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) N Key:ZQHFZHPUZXNPMF-UHFFFAOYSA-N N
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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.^[1]