IRSOGLADINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H7Cl2N5
Molecular Weight	256.091
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(=NC(N)=N1)C2=CC(Cl)=CC=C2Cl

InChI

InChIKey=ATCGGEJZONJOCL-UHFFFAOYSA-N

InChI=1S/C9H7Cl2N5/c10-4-1-2-6(11)5(3-4)7-14-8(12)16-9(13)15-7/h1-3H,(H4,12,13,14,15,16)

HIDE SMILES / InChI

Molecular Formula	C9H7Cl2N5
Molecular Weight	256.091
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/22950502

Irsogladine, a mucosal protective drug, was developed in Japan for the treatment of peptic ulcer disease and acute gastritis. Irsogladine increases intracellular cyclic adenosine 3',5'-monophosphate content via non-selective inhibition of phosphodiesterase isozymes and exhibits gastric cytoprotection partly mediated by endogenous nitric oxide. These effects may account for a variety of actions of irsogladine in the gastrointestinal tract, including facilitation of gap junctional intercellular communication, inhibition of the reduced gastric mucosal blood flow response, suppression of reactive oxygen generation and so on.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
3',5'-cyclic phosphodiesterase 5 Target ID: CHEMBL2363066 Sources: http://www.ncbi.nlm.nih.gov/pubmed/15302227	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Gastric ulcer 74 Sources: http://www.ncbi.nlm.nih.gov/pubmed/22950502	Preventing	Phase I 438	Unknown Approved Use Unknown
Peptic ulcer 72 Sources: http://www.ncbi.nlm.nih.gov/pubmed/22950502	Preventing	Phase I 438	Unknown Approved Use Unknown
Aphthous stomatitis 1 Sources: http://www.ncbi.nlm.nih.gov/pubmed/18989994	Preventing	Preclinical	Unknown Approved Use Unknown
Oral ulcers 1 Sources: http://www.ncbi.nlm.nih.gov/pubmed/18989994	Preventing	Preclinical	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
84 ng/mL EXPERIMENT https://akjournals.com/view/journals/1326/29/4/article-p459.xml	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:		IRSOGLADINE MALEATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
83.6 ng/mL EXPERIMENT https://akjournals.com/view/journals/1326/29/4/article-p459.xml	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:		IRSOGLADINE MALEATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
11005.4 ng × h/mL EXPERIMENT https://akjournals.com/view/journals/1326/29/4/article-p459.xml	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:		IRSOGLADINE MALEATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
11442.6 ng × h/mL EXPERIMENT https://akjournals.com/view/journals/1326/29/4/article-p459.xml	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:		IRSOGLADINE MALEATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
126.7 h EXPERIMENT https://akjournals.com/view/journals/1326/29/4/article-p459.xml	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:		IRSOGLADINE MALEATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
131.1 h EXPERIMENT https://akjournals.com/view/journals/1326/29/4/article-p459.xml	4 mg single, oral dose: 4 mg route of administration: Oral experiment type: SINGLE co-administered:		IRSOGLADINE MALEATE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P003RIQ	https://www.1pchem.com/search?query=1P003RIQ
1PlusChem LLC	1P00IAOU	https://www.1pchem.com/search?query=1P00IAOU
A2B Chem	AB74834	http://a2bchem.com/prod/AB74834
A2B Chem	AI52862	http://a2bchem.com/prod/AI52862
AbovChem LLC	HY-B0327A	http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-B0327A
AChemBlock	10707	http://www.achemblock.com/catalogsearch/result/?q=10707
AK Scientific	C762	https://aksci.com/item_detail.php?cat=C762
AK Scientific	G336	https://aksci.com/item_detail.php?cat=G336
AK Scientific	J10562	https://aksci.com/item_detail.php?cat=J10562
Angene	AGN-PC-0JK6NE	http://www.angenechemical.com/productshow/AGN-PC-0JK6NE.html
Angene	AGN-PC-0URYU1	http://www.angenechemical.com/productshow/AGN-PC-0URYU1.html
ApexBio Technology	B1593	https://www.apexbt.com/catalogsearch/result/?q=B1593
AstaTech	42326	http://astatechinc.com/CPSResult.php?CRNO=42326
AstaTech	42327	http://astatechinc.com/CPSResult.php?CRNO=42327
BLD Pharm	BD22825	http://www.bldpharm.com/search/Search.html?keyword=BD22825
BLD Pharm	BD41809	http://www.bldpharm.com/search/Search.html?keyword=BD41809
BOC Sciences	57381-26-7	http://www.bocsci.com/description.asp?cas=57381-26-7
BOC Sciences	57381-28-9	http://www.bocsci.com/description.asp?cas=57381-28-9
BOC Sciences	84504-69-8	http://www.bocsci.com/description.asp?cas=84504-69-8
Capot Chemical	14375	https://www.capotchem.com/search.do?q=14375
Chem Scene	CS-2368	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-2368
ChemShuttle	141479	https://www.chemshuttle.com/catalogsearch/result/?q=141479
Chemspace	CSC005861569	https://chem-space.com/CSC005861569
Combi-Blocks	QG-0720	http://www.combi-blocks.com/cgi-bin/find.cgi?QG-0720
eMolecules	19230722	https://orderbb.emolecules.com/search/#?query=19230722
eMolecules	43447191	https://orderbb.emolecules.com/search/#?query=43447191
eMolecules	48668408	https://orderbb.emolecules.com/search/#?query=48668408
eMolecules	901990	https://orderbb.emolecules.com/search/#?query=901990
Enamine	BBV-49384786	http://www.enaminestore.com/catalog/BBV-49384786
eNovation Chemicals	D754129	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D754129&searchbtn.x=0&searchbtn.y=0
eNovation Chemicals	D761114	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D761114&searchbtn.x=0&searchbtn.y=0
Hairui	HR132152	http://www.hairuichem.com/en/product/search.do?q=HR132152
Hairui	HR138983	http://www.hairuichem.com/en/product/search.do?q=HR138983
KeyOrganics	AS-11741	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-11741
KeyOrganics	HS-0056	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=HS-0056
Lab Network	LN01294940	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01294940
Lab Network	LN01343469	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01343469
Lab Seeker	SC-27337	http://www.labseeker.com/search.php?keywords=SC-27337&category=0
LabSeeker	SC-27337	http://www.labseeker.com/search.php?keywords=SC-27337&category=0
mcule	MCULE-1777550656	https://mcule.com/MCULE-1777550656/
mcule	MCULE-2335471667	https://mcule.com/MCULE-2335471667/
mcule	MCULE-3187363067	https://mcule.com/MCULE-3187363067/
MedChem Express	HY-B0327	https://www.medchemexpress.com/search.html?q=HY-B0327&ft=&fa=&fp=
Molnova	M18836	https://www.molnova.com/en/serch-list.html?keywords=M18836
MolPort	MolPort-005-935-126	https://www.molport.com/shop/molecule-link/MolPort-005-935-126
MolPort	MolPort-005-935-612	https://www.molport.com/shop/molecule-link/MolPort-005-935-612
PI Chemicals	PI-10749	http://www.pipharm.com/catalog_products/PI-10749.html
PI Chemicals	PI-24503	http://www.pipharm.com/catalog_products/PI-24503.html
Selleck Chemicals	S1929	http://www.selleckchem.com/search.html?searchDTO.searchParam=S1929
ShangHai Biochempartner	BCP21536	http://www.biochempartner.com/search_BCP21536
TargetMol	T6548	https://www.targetmol.com/search?keyword=T6548
Tetrahedron	TS28857	http://www.thsci.com/search.do?q=TS28857
Tetrahedron	TS80050	http://www.thsci.com/search.do?q=TS80050
Tocris	2504	https://www.tocris.com/search.php?Type=QuickSearch&Value=2504
Toronto Research Chemicals	B687735	https://www.trc-canada.com/product-detail/?CatNum=B687735
Toronto Research Chemicals	I777000	https://www.trc-canada.com/product-detail/?CatNum=I777000
Vesino Industrial Co Ltd	VA11104	http://www.vsnchem.com/search.do?a=s&psize=20&q=VA11104

PubMed

Title	Date	PubMed
Irsogladine: overview of the mechanisms of mucosal protective and healing- promoting actions in the gastrointestinal tract.	2013	22950502
Phosphodiesterase inhibition by a gastroprotective agent irsogladine: preferential blockade of cAMP hydrolysis.	2004-08-27	15302227

Patents

Sample Use Guides

In Vivo Use Guide

2-4 mg/day

Route of Administration: Oral

In Vitro Use Guide

irsogladine at higher concentration (10(-5) M) was unable to further increase cAMP level in the presence of non-selective phosphodiesterase (PDE) inhibitor 3-isobutyl-1-methylxanthine, although 3-isobutyl-1-methylxanthine by itself increased cAMP level.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:42:18 GMT 2025` Edited by `admin` on `Wed Apr 02 09:42:18 GMT 2025`
Record UNII	QBX79NZC1D
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IRSOGLADINE

Official Name

English

IRSOGLADINE [MI]

Preferred Name

English

Irsogladine [WHO-DD]

Common Name

English

NSC-759836

Code

English

2,4-DIAMINO-6-(2,5-DICHLOROPHENYL)-S-TRIAZINE

Systematic Name

English

irsogladine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29701