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Details

Stereochemistry ACHIRAL
Molecular Formula C14H17BrN6O2S3
Molecular Weight 477.423
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of EBROTIDINE

SMILES

NC(=N)NC1=NC(CSCCN\C=N\S(=O)(=O)C2=CC=C(Br)C=C2)=CS1

InChI

InChIKey=ZQHFZHPUZXNPMF-UHFFFAOYSA-N
InChI=1S/C14H17BrN6O2S3/c15-10-1-3-12(4-2-10)26(22,23)19-9-18-5-6-24-7-11-8-25-14(20-11)21-13(16)17/h1-4,8-9H,5-7H2,(H,18,19)(H4,16,17,20,21)

HIDE SMILES / InChI

Molecular Formula C14H17BrN6O2S3
Molecular Weight 477.423
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Ebrotidine is the first of a new generation of H2 receptor antagonists with gastroprotective activity It stimulates epithelial cell proliferative activity and produces beneficial physicochemical changes in the gastric mucus that contribute to its gastro-protective action against ethanol-, aspirin- or stress-induced gastric mucosal damage The antisecretory properties of ebrotidine are similar to those of ranitidine and approximately 10-fold greater than those of cimetidine This drug exhibits anti-Helicobacter pylori activity that is synergistic with a number of antibacterial agents; it inhibits the urease enzyme and the proteolytic and mucolytic activities of H. pylori, and counteracts the inhibitory effects of H. pylori lipopolysaccharide Ebrotidine is as effective as ranitidine for the treatment of patients with gastric or duodenal ulcers or erosive reflux oesophagitis Ebrotidine therapy results in significantly better ulcer healing rates than ranitidine treatment in patients who smoke. Ebrotidine was marketed in Spain in early 1997 and withdrawn in July 1998. Shortly after the drug was approved, several cases of acute liver injury were reported to the Regional Pharmacosurveillante Centers, the manufacturer and to a Registry of Hepatotoxicity in use in Southern Spain since 1994. On the basis of these cases the manufacturer withdrew ebrotidine from the market on 27 July 1998. This drug was also marketed in two other countries: Paraguay and Maurice Island.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P25021
Gene ID: 3274.0
Gene Symbol: HRH2
Target Organism: Homo sapiens (Human)
127.5 nM [Ki]
PubMed

PubMed

TitleDatePubMed
Acute liver injury associated with the use of ebrotidine, a new H2-receptor antagonist.
1999 Oct
Prevention and healing of experimental indomethacin-induced gastric lesions: effects of ebrotidine, omeprazole and ranitidine.
2000 Mar
Patents

Sample Use Guides

All patients were treated with a daily dose of 400 mg ebrotidine (the manufacturer’s recommended dose) except patient 3, who after 2 months on ebrotidine at 400 mg continued treatment at a reduced dose of 200 mg per day for 4 months. Duration of treatment ranged from 20 to 218 days.
Route of Administration: Oral
In Vitro Use Guide
Rat gastric mucosal segments were incubated in DMEM containing [3H]proline, [3H]glucosamine and [35S]Na2SO4 as markers for mucin synthesis, glycosylation and sulfation, in the presence of 0-150 uM ebrotidine. The drug, while showing no discernible effect on the apomucin synthesis, evoked a dose-dependent increase in mucin glycosylation and sulfation, which at 100 uM ebrotidine, attained its maximum of 2.4 and 2.7-fold stimulation, respectively. The analysis of mucin secretory responses revealed that ebrotidine caused a concentration-dependent enhancement in sulfomucin secretion which attained its maximum increase of 3.3-fold at 100-120 uM ebrotidine.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:34:15 GMT 2023
Edited
by admin
on Fri Dec 15 15:34:15 GMT 2023
Record UNII
TMZ3IBW2OW
Record Status Validated (UNII)
Record Version
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Name Type Language
EBROTIDINE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
ebrotidine [INN]
Common Name English
Ebrotidine [WHO-DD]
Common Name English
EBROTIDINE [MI]
Common Name English
EBROTIDINE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29702
Created by admin on Fri Dec 15 15:34:15 GMT 2023 , Edited by admin on Fri Dec 15 15:34:15 GMT 2023
Code System Code Type Description
SMS_ID
100000080502
Created by admin on Fri Dec 15 15:34:15 GMT 2023 , Edited by admin on Fri Dec 15 15:34:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID80143601
Created by admin on Fri Dec 15 15:34:15 GMT 2023 , Edited by admin on Fri Dec 15 15:34:15 GMT 2023
PRIMARY
CAS
100981-43-9
Created by admin on Fri Dec 15 15:34:15 GMT 2023 , Edited by admin on Fri Dec 15 15:34:15 GMT 2023
PRIMARY
WIKIPEDIA
EBROTIDINE
Created by admin on Fri Dec 15 15:34:15 GMT 2023 , Edited by admin on Fri Dec 15 15:34:15 GMT 2023
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NCI_THESAURUS
C77440
Created by admin on Fri Dec 15 15:34:15 GMT 2023 , Edited by admin on Fri Dec 15 15:34:15 GMT 2023
PRIMARY
DRUG CENTRAL
979
Created by admin on Fri Dec 15 15:34:15 GMT 2023 , Edited by admin on Fri Dec 15 15:34:15 GMT 2023
PRIMARY
ChEMBL
CHEMBL1742471
Created by admin on Fri Dec 15 15:34:15 GMT 2023 , Edited by admin on Fri Dec 15 15:34:15 GMT 2023
PRIMARY
EVMPD
SUB06438MIG
Created by admin on Fri Dec 15 15:34:15 GMT 2023 , Edited by admin on Fri Dec 15 15:34:15 GMT 2023
PRIMARY
MERCK INDEX
m4802
Created by admin on Fri Dec 15 15:34:15 GMT 2023 , Edited by admin on Fri Dec 15 15:34:15 GMT 2023
PRIMARY Merck Index
MESH
C075156
Created by admin on Fri Dec 15 15:34:15 GMT 2023 , Edited by admin on Fri Dec 15 15:34:15 GMT 2023
PRIMARY
FDA UNII
TMZ3IBW2OW
Created by admin on Fri Dec 15 15:34:15 GMT 2023 , Edited by admin on Fri Dec 15 15:34:15 GMT 2023
PRIMARY
PUBCHEM
65869
Created by admin on Fri Dec 15 15:34:15 GMT 2023 , Edited by admin on Fri Dec 15 15:34:15 GMT 2023
PRIMARY
INN
6009
Created by admin on Fri Dec 15 15:34:15 GMT 2023 , Edited by admin on Fri Dec 15 15:34:15 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY