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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
Structure of OSUTIDINE

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)

HIDE SMILES / InChI

Description
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.

CNS Activity

Curator's Comment: Osutidine was found in cerebrum of rats.

Originator

Curator's Comment: Osutidine had been licensed to Kowa for joint codevelopment and marketing.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P17124
Gene ID: 403812.0
Gene Symbol: HRH2
Target Organism: Canis lupus familiaris (Dog) (Canis familiaris)
2.3 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Histamine H2-receptor antagonism of T-593: studies on positive chronotropic responses in guinea pig atria.
1994 Apr
Histamine H2-receptor antagonism of T-593, an anti-ulcer agent: studies on aminopyrine accumulation in isolated canine gastric mucosal cells.
1998 Nov
Histamine H2 receptor antagonism by T-593: studies on cAMP generation in Hepa cells expressing histamine H2 receptor.
1999 Jul
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
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
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.
Name Type Language
OSUTIDINE
INN   JAN   WHO-DD  
INN  
Official Name English
OSUTIDINE [JAN]
Common Name English
Osutidine [WHO-DD]
Common Name English
osutidine [INN]
Common Name English
(±)-N-((E)-((P,.BETA.-DIHYDROXYPHENETHYL)AMINO)((2-((5-((METHYLAMINO)METHYL)FURFURYL)THIO)ETHYL)AMINO)METHYLENE)METHANESULFONAMIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29702
Created by admin on Fri Dec 15 17:15:49 GMT 2023 , Edited by admin on Fri Dec 15 17:15:49 GMT 2023
Code System Code Type Description
SMS_ID
100000083574
Created by admin on Fri Dec 15 17:15:49 GMT 2023 , Edited by admin on Fri Dec 15 17:15:49 GMT 2023
PRIMARY
INN
7511
Created by admin on Fri Dec 15 17:15:49 GMT 2023 , Edited by admin on Fri Dec 15 17:15:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID6040240
Created by admin on Fri Dec 15 17:15:49 GMT 2023 , Edited by admin on Fri Dec 15 17:15:49 GMT 2023
PRIMARY
PUBCHEM
132303
Created by admin on Fri Dec 15 17:15:49 GMT 2023 , Edited by admin on Fri Dec 15 17:15:49 GMT 2023
PRIMARY
CAS
140695-21-2
Created by admin on Fri Dec 15 17:15:49 GMT 2023 , Edited by admin on Fri Dec 15 17:15:49 GMT 2023
PRIMARY
NCI_THESAURUS
C90864
Created by admin on Fri Dec 15 17:15:49 GMT 2023 , Edited by admin on Fri Dec 15 17:15:49 GMT 2023
PRIMARY
ChEMBL
CHEMBL1742409
Created by admin on Fri Dec 15 17:15:49 GMT 2023 , Edited by admin on Fri Dec 15 17:15:49 GMT 2023
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EVMPD
SUB09477MIG
Created by admin on Fri Dec 15 17:15:49 GMT 2023 , Edited by admin on Fri Dec 15 17:15:49 GMT 2023
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FDA UNII
YDB1AQ7N4L
Created by admin on Fri Dec 15 17:15:49 GMT 2023 , Edited by admin on Fri Dec 15 17:15:49 GMT 2023
PRIMARY