Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H27O5S.Na |
Molecular Weight | 402.48 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[H][C@@]12CCC3=C(C=C(C(=C3)C(C)C)S([O-])(=O)=O)[C@@]1(C)CCC[C@@]2(C)C(O)=O
InChI
InChIKey=RCVIHORGZULVTN-YGJXXQMASA-M
InChI=1S/C20H28O5S.Na/c1-12(2)14-10-13-6-7-17-19(3,8-5-9-20(17,4)18(21)22)15(13)11-16(14)26(23,24)25;/h10-12,17H,5-9H2,1-4H3,(H,21,22)(H,23,24,25);/q;+1/p-1/t17-,19-,20-;/m1./s1
DescriptionSources: https://www.drugbank.ca/drugs/DB05265Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7574519 | https://www.ncbi.nlm.nih.gov/pubmed/7550119
Sources: https://www.drugbank.ca/drugs/DB05265
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7574519 | https://www.ncbi.nlm.nih.gov/pubmed/7550119
Ecabet is an anti-ulcer agent, marketed in Japan as an oral agent for treatment of gastric ulcers and gastritis. Ecabet eradicates Helicobacter pylori infection in gastric ulcer patients. Antibacterial effect of ecabet is demonstrated at low pH, is mediated by inhibition of bacterial urease and accompanied by interference with TLR4 signaling and pepsin inhibition. Ecabet is also investigated for the treatment of dry eye syndrome.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P18314 Gene ID: NA Gene Symbol: ureC Target Organism: Enterobacter aerogenes (Aerobacter aerogenes) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7550119 |
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Target ID: CHEMBL3295 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11256980 |
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Target ID: map04620 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15458921 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Sources: https://www.drugbank.ca/drugs/DB05265 |
Primary | Ecabet Na Approved UsePeptic ulcer disease |
PubMed
Title | Date | PubMed |
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Bacterial activity of a new antiulcer agent, ecabet sodium, against Helicobacter pylori under acidic conditions. | 1995 Jun |
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Mechanism of anti-urease action by the anti-ulcer drug ecabet sodium. | 1995 Jun |
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H pylori eradication: a randomized prospective study of triple therapy with or without ecabet sodium. | 2008 Feb 14 |
Patents
Sample Use Guides
For treatment of peptic ulcers, ecabet sodium is indicated orally, 1 g b.i.d. For treatment of dry eye syndrome, topical administration was used (one drop in study eye 4 times daily for 90 days).
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7574519
To measure bactericidal activity at pH 3.0, a liquid cultivation method was used. H. pylori NCTC 11637 was inoculated in 5 ml of brain heart infusion broth supplemented with 10% heat-inactivated fetal bovine serum and incubated at 378C for 48 h in an atmosphere of 5% O2–10% CO2–85% N2 with gyration. After rinsing with saline, bacterial cells were resuspended in saline to give about 109 CFU/ml. Reaction mixtures were prepared by adding 0.25 ml of an ecabet or BHA solution of citrate buffer supplemented with 10mM urea and incubated in a water bath at 37°C. Samples for viability (0.1 ml) were taken at 0, 15, 30, and 60 min. Viability was measured by the plate colony count technique. Ecabet showed concentration-dependent bactericidal effects at pHs 4.0 and 5.0, with MIC below 1 mg/ml.
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86408-72-2
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DTXSID4057847
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m4805
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DBSALT000062
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CHEMBL2104585
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51MO2B2OSB
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD