solid , 37762-06-4

Synonym(s):
1,4-Dihydro-5-(2-propoxyphenyl)-7H-1,2,3-triazolo(4,5-d)pyrimidin-7-one;1,4-Dihydro-5-(2-propoxyphenyl)-7H-1,2,3-triazolo[4,5-d]pyrimidine-7-one, M&B22948;Zaprinast - CAS 37762-06-4 - Calbiochem

CAS NO.：37762-06-4

Empirical Formula: C13H13N5O2

Molecular Weight: 271.27

MDL number: MFCD00214073

EINECS: 253-655-1

PRODUCT Properties

• Melting point: 237-238°C dec.
• Density: 1.48±0.1 g/cm3(Predicted)
• RTECS: XZ6157358
• storage temp.: Store at RT
• solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.11 mg/mL
• form: solid
• pka: 6.92±0.20(Predicted)
• color: white

Description and Uses

The cyclic nucleotide second messenger guanosine 3’5’-cyclic monophosphate (cGMP) is an important mediator of signal transduction and hence a wide range of cellular processes. It can be generated by soluble guanylyl cyclase in response to binding of nitric oxide and degraded via members of the phosphodiesterase (PDE) protein family. Zaprinast, the compound from which sildenafil (Viagra™) was developed, is a cGMP-specific phosphodiesterase inhibitor. It moderately inhibits PDE5 and PDE6 with IC₅₀ values of 0.5-0.76 and 0.15 μM, respectively, and weakly inhibits PDE9, PDE10, and PDE11 with IC₅₀ values of 35, 22, and 11-33 μM, respectively. Zaprinast therefore enhances the vasodilatory effects of nitric oxide in a range of vascular tissues by prolonging the cGMP-mediated activation of cGMP-dependent protein kinase. Zaprinast also activates both the rat and human G protein-coupled receptor, GPR35 with EC₅₀ values of 16 nM and 0.84 μM, respectively.

Zaprinast is a selective inhibitor of cyclic-GMP phosphodiesterase (PDE V, calmodulin insensitive). Since cGMP mediates the vasorelaxant action of nitric oxide, as well as the natriuretic and diuretic effect of at rial natriuretic factor (ANF) through the activation of PKG (cGMP dependent protein kinase), such inhibitors may display vasodilating, relaxant, and diuretic effects. These compounds may prove useful in treating hypertension and congestive heart failure.

Safety

• Symbol(GHS): GHS07
• Signal word: Warning
• Hazard statements: H315-H319-H335
• Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338
• Hazard Codes: Xi
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3