Irsogladine maleate Chemical Properties

Melting point:

181-182°C

storage temp. 

Inert atmosphere,Room Temperature

Water Solubility 

Insoluble in water

solubility 

DMF:30.0(Max Conc. mg/mL);80.61(Max Conc. mM)
DMSO:30.0(Max Conc. mg/mL);80.61(Max Conc. mM)
DMSO:PBS (pH 7.2) (1:3):0.25(Max Conc. mg/mL);0.67(Max Conc. mM)

form 

White crystalline powder.

color 

White to Almost white

Merck 

14,5102

InChI

InChI=1S/C9H7Cl2N5.C4H4O4/c10-4-1-2-6(11)5(3-4)7-14-8(12)16-9(13)15-7;5-3(6)1-2-4(7)8/h1-3H,(H4,12,13,14,15,16);1-2H,(H,5,6)(H,7,8)/b;2-1-

InChIKey

PJLVTVAIERNDEQ-BTJKTKAUSA-N

SMILES

N1=C(C2=CC(Cl)=CC=C2Cl)N=C(N)N=C1N.C(O)(=O)/C=C\C(O)=O

CAS DataBase Reference

84504-69-8(CAS DataBase Reference)

Safety Information

RTECS 

XY5930000

HS Code 

2933.69.6050

Toxicity

LD50 in male, female mice, rats (mg/kg): 6035, 5697, 3898, 2917 orally; 2841, 3216, 1600, 1524 s.c.; 775, 1006, 558, 545 i.p. (Ueda, 1984 p 474)

Irsogladine maleate Usage And Synthesis

Description

Irsogladine is a gastroprotective agent. It increases transfer of Lucifer yellow CH between isolated rabbit gastric epithelial cells, indicating enhanced gap junction intercellular communication (GJIC). Irsogladine (3 mg/kg) inhibits gastric mucosal lesion formation and decreases in gastric mucosal blood flow induced by monochloramine in rats, effects that can be prevented by the nitric oxide synthase inhibitor L-NAME . It also inhibits superoxide anion production induced by fMLP and increases cAMP levels in isolated human neutrophils in a concentration-dependent manner, similar to the phosphodiesterase 4 (PDE4) inhibitor rolipram .

Chemical Properties

White Solid

Uses

An anti-ulcer drug. Potent PDE4 inhibitor

Uses

antiulcerative;selective PDE4 inhibitor which also enhances gap junction intercellular communication

Definition

ChEBI: Irsogladine maleate is a dichlorobenzene.

Biological Activity

Phosphodiesterase 4 (PDE4) inhibitor that displays gastroprotective properties. Prevents gastric mucosal injury induced by monochloramine and ischemia-reperfusion. Activates gap-junctional intercellular communication improving gastric mucosal barrier function. Inhibits superoxide production in human neutrophils and inhibits in vitro and in vivo angiogenesis.

References

[1] TAKASHI KYOI. Irsogladine prevents monochloramine-induced gastric mucosal lesions by improving the decrease in mucosal blood flow due to the disturbance of nitric oxide synthesis in rats.[J]. Journal of pharmacological sciences, 2003, 93 3: 314-320. DOI: 10.1254/jphs.93.314
[2] F UEDA  T I  K Ban. Irsogladine activates gap-junctional intercellular communication through M1 muscarinic acetylcholine receptor.[J]. Journal of Pharmacology and Experimental Therapeutics, 1995, 274 2: 815-819.
[3] TAKASHI KYOI. Irsogladine, an anti-ulcer drug, suppresses superoxide production by inhibiting phosphodiesterase type 4 in human neutrophils[J]. Life sciences, 2004, 76 1: Pages 71-83. DOI: 10.1016/j.lfs.2004.06.016

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