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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H27O5S.Na.5H2O
Molecular Weight 492.557
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ECABET SODIUM PENTAHYDRATE

SMILES

O.O.O.O.O.[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=OWUMMAIYWPECON-HITVYADUSA-M
InChI=1S/C20H28O5S.Na.5H2O/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);;5*1H2/q;+1;;;;;/p-1/t17-,19-,20-;;;;;;/m1....../s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C20H28O5S
Molecular Weight 380.498
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P18314
Gene ID: NA
Gene Symbol: ureC
Target Organism: Enterobacter aerogenes (Aerobacter aerogenes)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Ecabet Na

Approved Use

Peptic ulcer disease
PubMed

PubMed

TitleDatePubMed
Bacterial activity of a new antiulcer agent, ecabet sodium, against Helicobacter pylori under acidic conditions.
1995 Jun
Mechanism of anti-urease action by the anti-ulcer drug ecabet sodium.
1995 Jun
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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:22:45 GMT 2023
Edited
by admin
on Sat Dec 16 05:22:45 GMT 2023
Record UNII
4DIV854Y8H
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ECABET SODIUM PENTAHYDRATE
Common Name English
Ecabet sodium pentahydrate [WHO-DD]
Common Name English
1-PHENANTHRENECARBOXYLIC ACID, 1,2,3,4,4A,9,10,10A-OCTAHYDRO-1,4A-DIMETHYL-7-(1-METHYLETHYL)-6-SULFO-, MONOSODIUM SALT, PENTAHYDRATE, (1R,4AS,10AR)-
Common Name English
ECABET SODIUM HYDRATE [JAN]
Common Name English
1-PHENANTHRENECARBOXYLIC ACID, 1,2,3,4,4A,9,10,10A-OCTAHYDRO-1,4A-DIMETHYL-7-(1-METHYLETHYL)-6-SULFO-, SODIUM SALT, HYDRATE (1:1:5), (1R,4AS,10AR)-
Common Name English
Code System Code Type Description
PUBCHEM
24892838
Created by admin on Sat Dec 16 05:22:45 GMT 2023 , Edited by admin on Sat Dec 16 05:22:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID00176390
Created by admin on Sat Dec 16 05:22:45 GMT 2023 , Edited by admin on Sat Dec 16 05:22:45 GMT 2023
PRIMARY
CAS
219773-47-4
Created by admin on Sat Dec 16 05:22:45 GMT 2023 , Edited by admin on Sat Dec 16 05:22:45 GMT 2023
PRIMARY
SMS_ID
300000038692
Created by admin on Sat Dec 16 05:22:45 GMT 2023 , Edited by admin on Sat Dec 16 05:22:45 GMT 2023
PRIMARY
FDA UNII
4DIV854Y8H
Created by admin on Sat Dec 16 05:22:45 GMT 2023 , Edited by admin on Sat Dec 16 05:22:45 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY