Irsogladine

Names

[ Name ]:
Irsogladine

[Synonym ]:
2',5'-Dichlorobenzoguanamine
1,3,5-Triazine-2,4-diamine, 6-(2,5-dichlorophenyl)-
MFCD00866871
Irsogladin
6-(2,5-Dichlorophenyl)-1,3,5-triazine-2,4-diamine
gaslon
Irsogladine
Dicloguamine

Biological Activity

[Description]:

Irsogladine is a PDE4 inhibitor and muscarinic acetylcholine receptor binder.Target: PDE4; mACHRIrsogladine treatment (300 and 500 mg/kg/day) resulted in a dose-dependent reduction of angiogenesis in wild-type mice by 21 and 45.3% (P < 0.02, P < 0.001), in tPA-deficient mice by 42.6 and 46% (P < 0.001, P < 0.001), and in uPA-deficient mice by 27.2 and 46% (P < 0.05, p < 0.001), respectively. Irsogladine inhibits bFGF-induced angiogenesis in wild-type, tPA-knockout, and uPA-knockout mice [1]. Irsogladine up-regulates GJIC between PC cells via regulation of the PKA pathway. It also suggests a useful adjuvant of Irsogladine to pancreatic cancer therapy [2]. irsogladine produces the increase of intracellular cAMP content via non-selective inhibition of PDE isozymes, which may be a key mechanism involved in its gastroprotective actions [3].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> mAChR

Signaling Pathways >> Neuronal Signaling >> mAChR

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE)

Research Areas >> Inflammation/Immunology

[References]

[1]. Ren, C.J., et al., Irsogladine maleate inhibits angiogenesis in wild-type and plasminogen activator-deficient mice. J Surg Res, 1998. 77(2): p. 126-31.

[2]. Kawasaki, Y., et al., Irsogladine malate up-regulates gap junctional intercellular communication between pancreatic cancer cells via PKA pathway. Pancreas, 2002. 25(4): p. 373-7.

[3]. Kyoi, T., et al., Phosphodiesterase inhibition by a gastroprotective agent irsogladine: preferential blockade of cAMP hydrolysis. Life Sci, 2004. 75(15): p. 1833-42.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
552.2±60.0 °C at 760 mmHg

[ Melting Point ]:
268-269°C

[ Molecular Formula ]:
C₉H₇Cl₂N₅

[ Molecular Weight ]:
256.091

[ Flash Point ]:
287.8±32.9 °C

[ Exact Mass ]:
255.007858

[ PSA ]:
90.71000

[ LogP ]:
2.08

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.706

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XY5850732

CHEMICAL NAME :: 1,3,5-Triazine-2,4-diamine, 6-(2,5-dichlorophenyl)-

CAS REGISTRY NUMBER :: 57381-26-7

LAST UPDATED :: 199712

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C9-H7-Cl2-N5

MOLECULAR WEIGHT :: 256.11

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1740 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4657907

Safety Information

[ Hazard Codes ]:
Xn,N

[ Risk Phrases ]:
R20:Harmful by inhalation. R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .

[ Safety Phrases ]:
S24-S61

[ RIDADR ]:
UN 2618 3/PG 3

[ WGK Germany ]:
2

[ RTECS ]:
WL5075900

[ Packaging Group ]:
III

[ Hazard Class ]:
3

[ HS Code ]:
2942000000

Customs

[ HS Code ]: 2942000000