Structure via PubChem · Public domain (PubChem)
ebrotidine
Sign in to saveEbrotidine is an H2 receptor antagonist with gastroprotective activity against ethanol-, aspirin- or stress-induced gastric mucosal damage. 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 wi
In the Vinony graph
Vinony's link graph records 330 inbound references to ebrotidine, and connects out to medication, ethanol and aspirin.
It is catalogued under topics including 4-Bromophenyl compounds, Amidines and Chemical pages without DrugBank identifier.
Vinony links it to 6 Wikipedia language editions.
Chemical data
- Formula
- C14H17BrN6O2S3
- Molecular weight
- 477.4 g/mol
- IUPAC name
- N-(4-bromophenyl)sulfonyl-N'-[2-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]ethyl]methanimidamide
- SMILES
- C1=CC(=CC=C1S(=O)(=O)NC=NCCSCC2=CSC(=N2)N=C(N)N)Br
- InChIKey
- ZQHFZHPUZXNPMF-UHFFFAOYSA-N
- XLogP
- 1.5
- Polar surface area
- 198 Ų
- H-bond donors
- 3
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
100 papers- Ebrotidine.Drugs · 1996
- [Ebrotidine].Gastroenterologia y hepatologia · 1997
- Anti-Helicobacter pylori activities of ebrotidine. A review of biochemical and animal experimental studies and data.Arzneimittel-Forschung · 1997
- [Ebrotidine-induced acute hepatitis].Gastroenterologia y hepatologia · 1999
- Ebrotidine--a nostrum for ulcer.Tropical gastroenterology : official journal of the Digestive Diseases Foundation · 1997
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 475.976
Show 5 more facts
- chemical formula
- C₁₄H₁₇BrN₆O₂S₃
- canonical SMILES
- C1=CC(=CC=C1S(=O)(=O)NC=NCCSCC2=CSC(=N2)N=C(N)N)Br
- isomeric SMILES
- C1=CC(=CC=C1S(=O)(=O)/N=C/NCCSCC2=CSC(=N2)NC(=N)N)Br
- subject has role
- H2 antagonists
- Commons category
- Ebrotidine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Ebrotidine is an H2 receptor antagonist with gastroprotective activity against ethanol-, aspirin- or stress-induced gastric mucosal damage. 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.
Excerpted from Wikipedia’s “ebrotidine” article, available under the CC BY-SA 4.0 licence.