Page last updated: 2024-12-06

ebrotidine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

ebrotidine: an H2-receptor antagonist and gastric mucosa protector [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65869
CHEMBL ID1742471
CHEBI ID135774
SCHEMBL ID33957
SCHEMBL ID33956
SCHEMBL ID8483555
MeSH IDM0202589

Synonyms (44)

Synonym
ebrotidine
fi-3542
ebrocit
ebrotidina [spanish]
4-bromo-n-(((2-(((-((diaminomethylene)amino)-4-thiazolyl)methyl)thio)ethyl)amino)methylene)benzenesulfonamide
ebrotidinum [latin]
benzenesulfonamide, n-(((2-(((2-((aminoiminomethyl)amino)-4-thiazolyl)methyl)thio)ethyl)amino)methylene)-4-bromo-, (e)-
ebrotiding
ebrotidine [inn]
p-bromo-n-(((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
100981-43-9
CHEBI:135774
n-(4-bromophenyl)sulfonyl-n'-[2-[[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]methylsulfanyl]ethyl]methanimidamide
ZINC03952167
ebrotidina
ebrotidinum
tmz3ibw2ow ,
ccris 8106
unii-tmz3ibw2ow
HY-15538
CS-1391
CHEMBL1742471
SCHEMBL33957
SCHEMBL33956
ebrotidine [mi]
ebrotidine [who-dd]
ebrotidine [mart.]
n-[[[2-[[[2-[(diaminomethylene)amino]-4-thiazolyl]methyl]thio]ethyl]amino]methylene]-4-bromo-benzenesulfonamide
ZQHFZHPUZXNPMF-UHFFFAOYSA-N
SCHEMBL8483555
DTXSID80143601
n-[(4-bromobenzene)sulfonyl]-n'-(2-{[(2-carbamimidamido-1,3-thiazol-4-yl)methyl]sulfanyl}ethyl)methanimidamide
p-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
Q5332065
fi 3542
BCP13341
fi3542
(e)-n'-((4-bromophenyl)sulfonyl)-n-(2-(((2-guanidinothiazol-4-yl)methyl)thio)ethyl)formimidamide
F84941
MS-28854
A910947
?ebrotidine
AKOS040741683

Research Excerpts

Overview

Ebrotidine is a new H2-receptor antagonist also known for its gastroprotective effect against ethanol-induced mucosal injury. It acts as a potent inhibitor of protease and lipase enzymes elaborated by Helicobacter pylori.

ExcerptReferenceRelevance
"Ebrotidine is a new H2-receptor antagonist also known for its gastroprotective effect against ethanol-induced mucosal injury. "( Regulation of gastric mucosal calcium channel activity by an antiulcer agent, ebrotidine.
Czajkowski, A; Liu, J; Piotrowski, J; Slomiany, A; Slomiany, BL; Yotsumoto, F, 1994
)
1.96
"Ebrotidine is a new H2-receptor antagonist which exhibits a remarkable ability for gastric mucosal protection. "( Metabolites of ebrotidine, a new H2-receptor antagonist, in human urine.
Albet, C; Anglada, L; Galcerán, MT; Rozman, E, 1994
)
2.08
"Ebrotidine is a new H2-receptor antagonist also known for its gastroprotective effect against ethanol-induced mucosal injury. "( Effect of ebrotidine on gastric mucosal calcium channel activity.
Czajkowski, A; Kawai, T; Liu, J; Slomiany, A; Slomiany, BL, 1993
)
2.13
"Ebrotidine is a new H2-receptor antagonist that, in addition to its antisecretory activity, exhibits a remarkable ability for gastric mucosal protection and acts as a potent inhibitor of protease and lipase enzymes elaborated by Helicobacter pylori. "( Investigation of the metabolism of ebrotidine in human urine by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry.
Albet, C; Anglada, L; Galceran, MT; Rozman, E, 1995
)
2.01
"Ebrotidine is a new H2-receptor antagonist with powerful antisecretory activity, demonstrated gastroprotection and the ability to inhibit protease and lipase activities of Helicobacter pylori. "( Determination of ebrotidine and its metabolites in human urine by reversed-phase ion-pair high-performance liquid chromatography.
Albet, C; Galcerán, MT; Rozman, E, 1997
)
2.08
"Ebrotidine is a new H2-receptor antagonist marketed in Spain in early 1997 and withdrawn in July 1998. "( Acute liver injury associated with the use of ebrotidine, a new H2-receptor antagonist.
Andrade, RJ; Bellot, V; Bermudez, F; Cárdenas, F; Fernandez, MC; Garcia-Escaño, MD; Gomez-Outes, A; Hervás, A; Lucena, MI; Martin-Vivaldi, R; Nogueras, F; Pelaez, G; Romero, M; Salmerón, J, 1999
)
2
"Ebrotidine is a new H2 receptor antagonist that potentiates the gastric mucosal barrier."( Prevention and healing of experimental indomethacin-induced gastric lesions: effects of ebrotidine, omeprazole and ranitidine.
Arroyo, MT; Lanas, A; Sáinz, R, 2000
)
1.97
"Ebrotidine is a novel H2-receptor antagonist that exhibits both gastroprotective and ulcer-healing properties. "( Gastroprotective and ulcer-healing activities of a new H2-receptor antagonist: ebrotidine.
Brzozowski, T; Konturek, SJ; Majka, J, 1992
)
1.95

Effects

Ebrotidine exerts a potent inhibitory action on the enzymatic activities directed towards mucus perimeter of gastric mucosal defense, causing a marked inhibition of H.

ExcerptReferenceRelevance
"Ebrotidine S,S-dioxide has been identified by HPLC using diode-array detection."( Metabolites of ebrotidine, a new H2-receptor antagonist, in human urine.
Albet, C; Anglada, L; Galcerán, MT; Rozman, E, 1994
)
1.36
"Ebrotidine has also been demonstrated to exert a potent inhibitory action on the enzymatic activities directed towards mucus perimeter of gastric mucosal defense, causing a marked inhibition of H."( Anti-Helicobacter pylori activities of ebrotidine. A review of biochemical and animal experimental studies and data.
Piotrowski, J; Slomiany, A; Slomiany, BL, 1997
)
1.29

Treatment

Treatment with ebrotidine caused accelerated ulcer healing (7 days), which was accompanied by a remarkable enhancement in the laminin receptor expression. Pretreatment with ebrotidine significantly reduced the endoscopic score of mucosal damage and deep hemorrhagic lesions.

ExcerptReferenceRelevance
"4. Treatment with ebrotidine caused accelerated ulcer healing (7 days), which was accompanied by a remarkable enhancement in the laminin receptor expression."( Gastric mucosal laminin receptor expression with ulcer healing by ebrotidine.
Czajkowski, A; Majka, J; Piotrowski, J; Slomiany, A; Slomiany, BL; Yotsumoto, F, 1994
)
0.85
"Treatment with ebrotidine caused accelerated ulcer healing (7 days) which was accompanied by a significant enhancement in receptor expression."( Gastric mucosal EGF and PDGF receptor expression with ulcer healing by ebrotidine.
Czajkowski, A; Piotrowski, J; Slomiany, A; Slomiany, BL; Yotsumoto, F, 1994
)
0.86
"Treatment with ebrotidine or ranitidine reduced significantly the endoscopic and self-assessment score, ebrotidine and ranitidine being equally effective in healing of esophageal mucosal lesions."( Double-blind crossover study of ranitidine and ebrotidine in gastro-esophageal reflux disease.
Konturek, SJ; Lorens, K; Maj, A; M[aczka, M; Sito, E; Thor, PJ, 1993
)
0.88
"Pretreatment with ebrotidine significantly reduced the endoscopic score of mucosal damage and deep hemorrhagic lesions caused by ethanol as compared with those in placebo-treated subjects."( Gastroprotective and antisecretory effects of ebrotidine.
Kaminski, K; Konturek, SJ; Maczka, J; Oleksy, J; Sito, E; Torres, J, 1992
)
0.87

Toxicity

Ebrotidine was more toxic in dogs than in rats. The most severe effects were the death or sacrifice in extremis of two dogs from the high dose group which had undergone rectal prolapse. No deaths occurred in the rats.

ExcerptReferenceRelevance
"Ebrotidine 800 mg is as effective and safe as ranitidine 300 mg in healing duodenal ulcer, but ebrotidine appears to be superior in promoting the healing of duodenal ulceration in smokers."( Efficacy and safety of ebrotidine compared with ranitidine in patients with duodenal ulcer.
Butruk, E; Dzieniszewski, J; Gabryelewicz, A; Konturek, SJ; Marlicz, K; Marquez, M; Nowak, A; Ortiz, JA; Torres, J, 1995
)
2.04
" LD50 values for the oral route were indeterminable in all cases."( Acute toxicity studies of ebrotidine.
Grau, MT; Ortiz, JA; Romero, A; Sacristán, A; Villamayor, F, 1997
)
0.6
" Probably due to its pharmacokinetics, ebrotidine was more toxic in dogs than in rats, since the most severe effects were the death or sacrifice in extremis of two dogs from the high dose group which had undergone rectal prolapse, while no deaths occurred in the rats."( Subacute toxicity of ebrotidine in rats and dogs.
Grau, MT; Ortiz, JA; Romero, A; Sacristán, A; Villamayor, F, 1997
)
0.89
" The maximum toxic effect-free level was 50 mg/kg for both rats and dogs, which provides a wide safety margin with respect to the therapeutic dose."( Chronic toxicity of ebrotidine in rats and dogs.
Grau, MT; Ortiz, JA; Romero, A; Sacristán, A; Villamayor, F, 1997
)
0.62
" Among the different doses used in both animal species, the maximum toxic effect-free dose was that of 25 mg/kg."( Toxicity of ebrotidine on reproduction. Toxicity on fertility and general reproductive performance, embryo-fetal toxicity and peri- and postnatal toxicity.
Grau, MT; Ortiz, JA; Romero, A; Sacristán, A; Villamayor, F, 1997
)
0.68
" Results showed that a daily dose of 400 mg ebrotidine is effective and safe in the treatment of duodenal ulcers."( Comparison of the efficacy and safety of ebrotidine in the treatment of duodenal ulcer. A multicentre, double-blind, placebo-controlled phase II study.
Aldeguer, M; Chantar, C; Czajkowski, A; Gabryelewicz, A; Luca de Tena, F; Marlicz, K; Márquez, M; Ortiz, JA; Skrodzka, D; Torres, J, 1997
)
0.82

Pharmacokinetics

The safety of ebrotidine (N-[(E)-[[[2-[(diaminomethylene)amino]-4- thiazolyl]methyl]thio]ethyl]amino] methylene], a new H2-receptor antagonist with gastroprotective activity, was assessed. The basic pharmacokinetic parameters were determined after its oral administration to healthy volunteers.

ExcerptReferenceRelevance
"The tolerability and safety of ebrotidine (N-[(E)-[[2-[[[2-[(diaminomethylene)amino]-4-thiazolyl]methyl] thio]ethyl]amino]methylene]-4-bromo-benzenesulfonamide, CAS 100981-43-9, FI-3542) and its basic pharmacokinetic parameters were determined after its oral administration to healthy volunteers."( Tolerability and pharmacokinetics of ebrotidine in healthy subjects given single and repeated oral doses.
Albet, C; Badenas, JM; Farré, M; Herrero, E; Márquez, M; Ortiz, JA; Roset, PN; Ugena, B, 1997
)
0.86
"The safety of ebrotidine (N-[(E)-[[2-[[[2-[(diaminomethylene)amino]-4- thiazolyl]methyl]thio]ethyl]amino] methylene]-4-bromo-benzenesulfonamide, CAS 100981-43-9, FI-3542), a new H2-receptor antagonist with gastroprotective activity, was assessed and its main pharmacokinetic parameters were determined in order to establish the dose linearity after the repeated administration of three different dose levels."( Pharmacokinetic study of ebrotidine administered in multiple doses to healthy volunteers for 4 days.
Albet, C; Carcas, AJ; Esteban, C; Frías, J; Márquez, M; Ortiz, JA; Sánchez-García, P; Torres, J, 1997
)
0.96
"Several clinical pharmacokinetic studies of ebrotidine (N-[(E)-[[2-[[[2-[(diaminomethylene)amino]-4-thiazolyl] methyl]thio]ethyl]amino]methylene]-4-bromo-benzenesulfonamide, CAS 100981-43-9, FI-3542) administered by oral route in single and multiple doses to healthy volunteers have been performed."( Pharmacokinetics of ebrotidine in healthy volunteers. A summary.
Albet, C; Herrero, E; Márquez, M; Ortiz, JA; Pérez, JA; Rozman, E, 1997
)
0.88

Compound-Compound Interactions

ExcerptReferenceRelevance
"This double-blind, randomized, phase III clinical trial was carried out in two parallel groups to assess the efficacy of ebrotidine (N-[(E)-[[2-[[[2-[(diaminomethylene) amino]-4-thiazolyl]methyl]thio]ethyl]amino] methylene]-4-bromo-benzenesulfonamide, CAS 100981-43-9, FI-3542) 400 mg and ranitidine 300 mg given in single evening dose, combined with amoxicillin 750 mg and metronidazole 500 mg three times daily for 14 days, in the eradication of Helicobacter pylori in patients with duodenal ulcer."( Efficacy of ebrotidine and ranitidine combined with amoxicillin and metronidazole in the eradication of Helicobacter pylori in patients with duodenal ulcer.
Fillat, O; Herrero, E; Karcz, D; Kulig, J; Márquez, M; Ortiz, JA; Popiela, T; Tabor, J; Torres, J, 1997
)
0.88

Bioavailability

ExcerptReferenceRelevance
" Absolute bioavailability was 22% of the dose administered."( Pharmacokinetics of ebrotidine in rats and dogs.
Albet, C; Ortiz, JA; Pérez, JA; Sacristán, A, 1997
)
0.62

Dosage Studied

ExcerptRelevanceReference
" A dose range toxicity study was also performed to determine the dosage levels or concentrations to be tested for the assessment of genotoxic effects."( Genotoxicity studies on ebrotidine.
Ciliutti, P; García, M; Marcos, R; Montero, R; Palacín, C; Romero, A; Vericat, JA; Villamayor, F, 1997
)
0.6
" Dosage levels were 150, 300, 400, 500, 600 and 800 mg."( Pharmacokinetics of ebrotidine in healthy volunteers. A summary.
Albet, C; Herrero, E; Márquez, M; Ortiz, JA; Pérez, JA; Rozman, E, 1997
)
0.62
" We proposed a systematic classification scheme using FDA-approved drug labeling to assess the DILI potential of drugs, which yielded a benchmark dataset with 287 drugs representing a wide range of therapeutic categories and daily dosage amounts."( FDA-approved drug labeling for the study of drug-induced liver injury.
Chen, M; Fang, H; Liu, Z; Shi, Q; Tong, W; Vijay, V, 2011
)
0.37
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
sulfonamideAn amide of a sulfonic acid RS(=O)2NR'2.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID625293Drug Induced Liver Injury Prediction System (DILIps) validation dataset; compound DILI positive/negative as observed in LTKB-BD2011PLoS computational biology, Dec, Volume: 7, Issue:12
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1474167Liver toxicity in human assessed as induction of drug-induced liver injury by measuring verified drug-induced liver injury concern status2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
AID625276FDA Liver Toxicity Knowledge Base Benchmark Dataset (LTKB-BD) drugs of most concern for DILI2011Drug discovery today, Aug, Volume: 16, Issue:15-16
FDA-approved drug labeling for the study of drug-induced liver injury.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1474166Liver toxicity in human assessed as induction of drug-induced liver injury by measuring severity class index2016Drug discovery today, Apr, Volume: 21, Issue:4
DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (89)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's80 (89.89)18.2507
2000's6 (6.74)29.6817
2010's3 (3.37)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.90

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index18.90 (24.57)
Research Supply Index4.73 (2.92)
Research Growth Index4.33 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.90)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials18 (19.15%)5.53%
Reviews10 (10.64%)6.00%
Case Studies6 (6.38%)4.05%
Observational0 (0.00%)0.25%
Other60 (63.83%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]