| Identification | More | [Name]
Irsogladine | [CAS]
57381-26-7 | [Synonyms]
rsogladin
IRSOGLADINE
Dicloguamine
Irsogladine free base
2',5'-Dichlorobenzoguanamine
5-triazine-2,4-diamine,6-(2,5-dichlorophenyl)-3
6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine
2,4-diamino-6-(2,5-dichlorophenyl)-1,3,5-triazine
Irsogladine,2,4-DiaMino-6-(2,5-dichlorophenyl)-1,3,5-triazine | [Molecular Formula]
C9H7Cl2N5 | [MDL Number]
MFCD00866871 | [Molecular Weight]
256.09 | [MOL File]
57381-26-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
268-269°C | [Boiling point ]
552.2±60.0 °C(Predicted) | [density ]
1.572 | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
insoluble in H2O; insoluble in EtOH; ≥12.80 mg/mL in DMSO | [form ]
solid | [pka]
3.88±0.10(Predicted) | [color ]
White to off-white | [CAS DataBase Reference]
57381-26-7(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
Irsogladine is a PDE4 inhibitor and muscarinic acetylcholine receptor binder.
Target: PDE4; mACHR
Irsogladine 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]. | [Definition]
ChEBI: 6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine is a dichlorobenzene. | [Biological Activity]
irsogladine is a pde4 inhibitor and muscarinic acetylcholine receptor binder.irsogladine 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 mic | [IC 50]
PDE4 | [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. DOI:10.1006/jsre.1998.5381
[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. DOI:10.1097/00006676-200211000-00009
[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. DOI:10.1016/j.lfs.2004.03.022 |
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