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Irsogladine

Product Name
Irsogladine
CAS No.
57381-26-7
Chemical Name
Irsogladine
Synonyms
Isoladine;Irsogladin;IRSOGLADINE;Irosgladine;Dicloguamine;Irsogladine free base;Irsogladine USP/EP/BP;Irsogladine, 10 mM in DMSO;2',5'-Dichlorobenzoguanamine;5-triazine-2,4-diamine,6-(2,5-dichlorophenyl)-3
CBNumber
CB7767928
Molecular Formula
C9H7Cl2N5
Formula Weight
256.09
MOL File
57381-26-7.mol
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Irsogladine Property

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)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

ApexBio Technology
Product number
B1593
Product name
Irsogladine
Packaging
50mg
Price
$40
Updated
2021/12/16
ApexBio Technology
Product number
B1593
Product name
Irsogladine
Packaging
10mM(in 1mL DMSO)
Price
$50
Updated
2021/12/16
ChemScene
Product number
CS-2368
Product name
Irsogladine
Purity
99.80%
Packaging
500mg
Price
$50
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0007238
Product name
IRSOGLADINE
Purity
95.00%
Packaging
25MG
Price
$141.75
Updated
2021/12/16
AK Scientific
Product number
C762
Product name
Irsogladine
Packaging
500mg
Price
$282
Updated
2021/12/16
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Irsogladine Chemical Properties,Usage,Production

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

Synthesis

84504-69-8

57381-26-7

General procedure for the synthesis of 6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine x maleate from 6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine: 6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine x maleate (0.3 g, 0.80 mmol) was dissolved in ethyl acetate ( 50 mL) and the reaction was stirred with saturated NaHCO3 solution (50 mL) for 1 hour at room temperature. After completion of the reaction, the organic layer was separated and washed with distilled water. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the target product 6-(2,5-dichlorophenyl)-1,3,5-triazine-2,4-diamine in 70% yield.

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

Irsogladine Preparation Products And Raw materials

Raw materials

Dicyandiamide Ethanol Maleic acid Potassium hydroxide 2,5-DICHLOROTOLUENE 1,4-Dioxane Sulfamic acid 2,5-Dichlorobenzoic acid 2,5-Dichlorobenzonitrile Potassium permanganate Irsogladine maleate

Preparation Products

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Irsogladine Suppliers

China 127 Europe 2 Germany 1 India 2 United Kingdom 4 United States 23 Global 159
LGM Pharma
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View Lastest Price from Irsogladine manufacturers

Career Henan Chemical Co
Product
Irsogladine 57381-26-7
Price
US $7.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100KG
Release date
2018-12-18

57381-26-7, IrsogladineRelated Search:

Diisopropylammonium dichloroacetate Iminodiacetonitrile Dichlorodimethylsilane 1,3,5-Triazine Iminodiacetic acid Dichlorodiphenylsilane 4,4'-Methylenedianiline Irsogladine Impurity GDT Irsogladine Impurity TMSM2 Chlorobenzene Famciclovir Irsogladine maleate IRSOGLADINE MALEATE Irsogladine 4-(4,6-Diamino-s-triazinyl)-2,5-dichlorophenol 3-(4,6-Diamino-s-triazinyl)-2,5-dichlorophenol 3-Pyridinecarboxamide, N-(4-(2,5-dichlorophenyl)-6-(1-piperidinyl)-1,3 ,5-triazin-2-yl)- 3-Pyridinecarboxamide, N-(4-(2,5-dichlorophenyl)-6-(4-morpholinyl)-1,3 ,5-triazin-2-yl)-

  • 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
  • Irsogladin
  • Irsogladine,2,4-DiaMino-6-(2,5-dichlorophenyl)-1,3,5-triazine
  • IRSOGLADINE
  • Irsogladine free base
  • 2',5'-Dichlorobenzoguanamine
  • Dicloguamine
  • Irosgladine
  • 1,3,5-Triazine-2,4-diamine, 6-(2,5-dichlorophenyl)-
  • Irsogladine USP/EP/BP
  • Isoladine
  • Irsogladine, 10 mM in DMSO
  • 57381-26-7
  • C9H7Cl2N5Q
  • Active Pharmaceutical Ingredients
  • pharmaceutical intermediates
  • Inhibitors