ECABET

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H28O5S
Molecular Weight	380.498
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C1=C(C=C2C(CC[C@H]3[C@@](C)(CCC[C@]23C)C(O)=O)=C1)S(O)(=O)=O

InChI

InChIKey=IWCWQNVIUXZOMJ-MISYRCLQSA-N

InChI=1S/C20H28O5S/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)/t17-,19-,20-/m1/s1

HIDE SMILES / InChI

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

Description
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
Urease subunit alpha 3 Target ID: P18314 Gene ID: NA Gene Symbol: ureC Target Organism: Enterobacter aerogenes (Aerobacter aerogenes) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7550119	Inhibitor 8504
Pepsin A 6 Target ID: CHEMBL3295 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11256980	Inhibitor 8504
Toll-like receptor signaling pathway 3 Target ID: map04620 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15458921	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dry eye syndrome 21 Sources: https://clinicaltrials.gov/ct2/show/NCT00198536	Primary		Phase III 665	Unknown Approved Use Unknown
Peptic ulcer 72 Sources: https://www.drugbank.ca/drugs/DB05265	Primary		Approved 8583	Ecabet Na Approved Use Peptic ulcer disease

C_max

Value	Dose	Co-administered	Analyte	Population
4926 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18258501/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		ECABET plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
36943 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18258501/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		ECABET plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.63 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18258501/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		ECABET plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
1 g 2 times / day multiple, oral Studied dose Dose: 1 g, 2 times / day Route: oral Route: multiple Dose: 1 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18299710/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18299710/	Disc. AE: Vertigo, Epigastric pain... Other AEs: Nausea, Swelling face... AEs leading to discontinuation/dose reduction: Vertigo Epigastric pain Other AEs: Nausea Swelling face Sources: https://pubmed.ncbi.nlm.nih.gov/18299710/

AEs

AE	Significance	Dose	Population
Nausea		1 g 2 times / day multiple, oral Studied dose Dose: 1 g, 2 times / day Route: oral Route: multiple Dose: 1 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18299710/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18299710/
Swelling face		1 g 2 times / day multiple, oral Studied dose Dose: 1 g, 2 times / day Route: oral Route: multiple Dose: 1 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18299710/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18299710/
Epigastric pain	Disc. AE	1 g 2 times / day multiple, oral Studied dose Dose: 1 g, 2 times / day Route: oral Route: multiple Dose: 1 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18299710/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18299710/
Vertigo	Disc. AE	1 g 2 times / day multiple, oral Studied dose Dose: 1 g, 2 times / day Route: oral Route: multiple Dose: 1 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18299710/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/18299710/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 2052

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/65781#section=BioAssay-Results Page: 39.0	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/65781#section=BioAssay-Results Page: 37 \| 39	no

PubMed

Title	Date	PubMed
H pylori eradication: a randomized prospective study of triple therapy with or without ecabet sodium.	2008-02-14	18240348
Bacterial activity of a new antiulcer agent, ecabet sodium, against Helicobacter pylori under acidic conditions.	1995-06	7574519
Mechanism of anti-urease action by the anti-ulcer drug ecabet sodium.	1995-06	7550119

Patents

Sample Use Guides

In Vivo Use Guide

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 `Mon Mar 31 18:18:42 GMT 2025` Edited by `admin` on `Mon Mar 31 18:18:42 GMT 2025`
Record UNII	2K02669KWP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ECABET

Official Name

English

ECABET [MI]

Preferred Name

English

ecabet [INN]

Common Name

English

13-ISOPROPYL-12-SULFOPODOCARPA-8,11,13-TRIEN-15-OIC ACID

Common Name

English

Ecabet [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C783