Basic information
- CAS
100981-43-9- Standard SMILES
NC(N)=Nc1nc(CSCCN=CNS(=O)(=O)c2ccc(Br)cc2)cs1- InChIKey
ZQHFZHPUZXNPMF-UHFFFAOYSA-N- Molecular formula
- C14H17BrN6O2S3
- Average molar mass
- 477.4 g/mol
- Monoisotopic mass
- 475.97585
Overview
Ebrotidine is a sulfonamide.
Names & identifiers
- Preferred name
- Ebrotidine
- IUPAC
- N-(4-bromophenyl)sulfonyl-N'-[2-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]ethyl]methanimidamide
- English name
- Ebrotidine
- Molecular formula
- C14H17BrN6O2S3
- Molecular weight
- 477.42
Names & synonyms
Ebrotidine100981-43-9EbrotidinaEbrotidinumTMZ3IBW2OWDTXSID801436014-bromo-N-(((2-(((-((diaminomethylene)amino)-4-thiazolyl)methyl)thio)ethyl)amino)methylene)benzenesulfonamideN-((4-bromobenzene)sulfonyl)-N'-(2-(((2-carbamimidamido-1,3-thiazol-4-yl)methyl)sulfanyl)ethyl)methanimidamideN-[(4-bromobenzene)sulfonyl]-N'-(2-{[(2-carbamimidamido-1,3-thiazol-4-yl)methyl]sulfanyl}ethyl)methanimidamideRefChem:136183DTXCID4066092FI-3542
Show more names
FI3542UlsanicFI 3542Ebrotidine, 10 mM in DMSOFI 3542ULSANICFI3542Ebrotidine,FI 3542,Histamine Receptor,inhibit,Inhibitor,FI-3542(E)-N-[[[2-[[[2-[(Aminoiminomethyl)amino]-4-thiazolyl]methyl]thio]ethyl]amino]methylene]-4-bromobenzenesulfonamide
Ebrotidine [INN]N-(4-bromophenyl)sulfonyl-N'-[2-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]ethyl]methanimidamideEbrotiding(E)-N'-((4-bromophenyl)sulfonyl)-N-(2-(((2-guanidinothiazol-4-yl)methyl)thio)ethyl)formimidamideEbrotidinum [Latin]Ebrotidina [Spanish]Ebrocitp-Bromo-N-[(E)-({2-[({2-[(diaminomethylene)amino]-4-thiazolyl}methyl)thio]ethyl}amino)methylene]benzenesulfonamide;p-Bromo-N-[(E)-({2-[({2-[(diaminomethylene)amino]-4-thiazolyl}methyl)thio]ethyl}amino)methylene]benzenesulfonamide
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 198 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 9
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 586
Physicochemical properties
- Melting point
- 142.5 · 142.5-146℃
- Boiling point
- 633 · 633.0±65.0 °C(Predicted)
- Density
- 1.73 · 1.73±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Amber Vial, -20°C Freezer, Under inert atmosphere
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 5.25 · 5.25±0.40(Predicted)
- form
- Solid
- color
- White to Off-White
- Stability
- Light Sensitive
- FDA UNII
- 3 IBW2OW · TMZ3IBW2OW
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Ebrotidine
vMost-DILI-concern
8
Withdrawn
DOI:10.1016/j.drudis.2016.02.015
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief.
Drugs that selectively bind to but do not activate histamine H2 receptors, thereby blocking the actions of histamine. Their clinically most important action is the inhibition of acid secretion in the treatment of gastrointestinal ulcers. Smooth muscle may also be affected. Some drugs in this class have strong effects in the central nervous system, but these actions are not well understood.
Applications
DescriptionEbrocit 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.
UsesEbrotidine is a H2 receptor antagonist that has shown gastroprotective properties against gastric mucosal damange.
Suppliers29 total
阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]
Career Henan Chemica Co
Related reactions
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Compound notes
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