Details
Stereochemistry | RACEMIC |
Molecular Formula | C19H28N4O5S2 |
Molecular Weight | 456.579 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CNCC1=CC=C(CSCCN\C(NCC(O)C2=CC=C(O)C=C2)=N\S(C)(=O)=O)O1
InChI
InChIKey=GZPOYVTZKHVRHE-UHFFFAOYSA-N
InChI=1S/C19H28N4O5S2/c1-20-11-16-7-8-17(28-16)13-29-10-9-21-19(23-30(2,26)27)22-12-18(25)14-3-5-15(24)6-4-14/h3-8,18,20,24-25H,9-13H2,1-2H3,(H2,21,22,23)
DescriptionSources: http://adisinsight.springer.com/drugs/800002012Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/10352421
https://www.ncbi.nlm.nih.gov/pubmed/7914553
http://www.lifescience.co.jp/yk/yk00/yke00s2.html
Sources: http://adisinsight.springer.com/drugs/800002012
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/10352421
https://www.ncbi.nlm.nih.gov/pubmed/7914553
http://www.lifescience.co.jp/yk/yk00/yke00s2.html
Osutidine (T-593) is a H2 receptor antagonist which was undergoing development by Toyama Chemical for the treatment of peptic/gastric and duodenal ulcers. It is a beta-hydroxyphenethylamine derivative with both antisecretory and cytoprotective properties. Osutidine inhibited the histamine-induced cAMP generation in a concentration-dependent manner. Osutidine suppressed the maximal response of the histamine-induced positive chronotropic response, indicating that the compound is unsurmountable H2-antagonists. The metabolism of Osutidine in humans may not differ from that of rodents and dogs. No clinically relevant accumulation occurred following repeated dosage. In the single oral and subcutaneous dose toxicity studies in rats, there were no dead animals. The oral LD50 value was greater than 5 g/kg for both sexes, and there was no abnormality in general signs. An oral formulation of the drug was in phase III clinical trials in Japan, however Toyama has dropped it from clinical development.
Originator
Sources: https://business.highbeam.com/436989/article-1G1-71765417/osutidine-toyama-discontinued-japan
Curator's Comment: Osutidine had been licensed to Kowa for joint codevelopment and marketing.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P17124 Gene ID: 403812.0 Gene Symbol: HRH2 Target Organism: Canis lupus familiaris (Dog) (Canis familiaris) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10352421 |
2.3 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Histamine H2-receptor antagonism of T-593: studies on positive chronotropic responses in guinea pig atria. | 1994 Apr |
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Histamine H2-receptor antagonism of T-593, an anti-ulcer agent: studies on aminopyrine accumulation in isolated canine gastric mucosal cells. | 1998 Nov |
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Histamine H2 receptor antagonism by T-593: studies on cAMP generation in Hepa cells expressing histamine H2 receptor. | 1999 Jul |
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Effects of osutidine (T-593) and its enantiomers on gastric mucosal hemodynamics and mucosal integrity in anesthetized rats. | 2001 Jan |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.lifescience.co.jp/yk/yk00/ab_s2/ab17.htm
Curator's Comment: It is confirmed that 800 mg of Osutidine (T-593) given twice daily is useful for promoting the healing of gastric and duodenal ulcers.
Twice daily in a dose of 400 mg, 8 weeks to patients with gastric ulcer and for 6 weeks to patients with duodenal ulcer
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10352421
Hepa cells (derived from a rat hepatoma cell line) were transfected with the canine histamine H2 receptor. The expressed receptor was selective to H2, but not H1, receptor. The inhibitory effect of Osutidine (T-593) on cellular cAMP generation stimulated by 1E-5 mol/l histamine was studied in Hepa cells expressing the canine histamine H2 receptor. T-593 inhibited the histamine-induced cAMP generation in a concentration-dependent manner, with IC50 values of 2.3E-6 mol/l.
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C29702
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ACTIVE MOIETY