OSUTIDINE

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 Search

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

Molecular Formula	C19H28N4O5S2
Molecular Weight	456.579
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	1
Optical Activity	( + / - )

Description
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H2 receptor 46 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	Antagonist 2849		2.3 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Duodenal ulcer 49 Sources: http://www.lifescience.co.jp/yk/yk00/ab_s2/ab17.htm	Primary	Phase III 665	Unknown Approved Use Unknown
Gastric ulcer 74 Sources: http://www.lifescience.co.jp/yk/yk00/ab_s2/ab17.htm	Primary	Phase III 665	Unknown Approved Use Unknown
Reflux esophagitis 3 Sources: http://www.lifescience.co.jp/yk/yk00/ab_s2/ab20.htm	Primary	Phase II 1147	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
400 mg 2 times / day multiple, oral Highest studied dose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: https://www.researchgate.net/publication/288652229_Clinical_efficacy_of_T-593_Osutidine_on_gastric_ulcer_resistant_to_H2-receptor_antagonist_andor_proton_pump_inhibitor	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.researchgate.net/publication/288652229_Clinical_efficacy_of_T-593_Osutidine_on_gastric_ulcer_resistant_to_H2-receptor_antagonist_andor_proton_pump_inhibitor	Sources: https://www.researchgate.net/publication/288652229_Clinical_efficacy_of_T-593_Osutidine_on_gastric_ulcer_resistant_to_H2-receptor_antagonist_andor_proton_pump_inhibitor
200 mg 2 times / day multiple, oral Studied dose Dose: 200 mg, 2 times / day Route: oral Route: multiple Dose: 200 mg, 2 times / day Sources: https://www.researchgate.net/publication/288387050_Clinical_effects_of_T-593_Osutidine_on_endocrine_function_and_healing_in_patients_with_peptic_ulcer	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.researchgate.net/publication/288387050_Clinical_effects_of_T-593_Osutidine_on_endocrine_function_and_healing_in_patients_with_peptic_ulcer	Sources: https://www.researchgate.net/publication/288387050_Clinical_effects_of_T-593_Osutidine_on_endocrine_function_and_healing_in_patients_with_peptic_ulcer

PubMed

Title	Date	PubMed
Effects of osutidine (T-593) and its enantiomers on gastric mucosal hemodynamics and mucosal integrity in anesthetized rats.	2001-01	11215325
Histamine H2 receptor antagonism by T-593: studies on cAMP generation in Hepa cells expressing histamine H2 receptor.	1999-07	10352421
Histamine H2-receptor antagonism of T-593, an anti-ulcer agent: studies on aminopyrine accumulation in isolated canine gastric mucosal cells.	1998-11	9869265
Histamine H2-receptor antagonism of T-593: studies on positive chronotropic responses in guinea pig atria.	1994-04	7914553

Sample Use Guides

In Vivo Use Guide

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

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:43:14 GMT 2025` Edited by `admin` on `Mon Mar 31 18:43:14 GMT 2025`
Record UNII	YDB1AQ7N4L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OSUTIDINE [JAN]

Preferred Name

English

OSUTIDINE

Official 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