37762-06-4

Basic information

• Product Name: ZAPRINAST
• Synonyms: 1,4-DIHYDRO-5-[2-PROPOXYPHENYL]-7H-1,2,3-TRIAZOLO[4,5-D]PYRIMIDINE-7-ONE;2-(2-PROPYLOXYPHENYL)-8-AZAPURIN-6-ONE;M AND B 22948;M-EPSILON-TB22948;ZAPRINAST;2-(2-Propoxyphenyl)-6-hydroxy-8-azapurine;1,4-dihydro-5-(2-propoxyphenyl)-7h-1,2,3-triazolo(4,5-d)pyrimidin-7-one;2-(2-Propoxyphenyl)-8-azahypoxanthine
• CAS NO: 37762-06-4
• Molecular Formula: C₁₃H₁₃N₅O₂
• Molecular Weight: 271.27
• EINECS: 253-655-1
• Product Categories: All Inhibitors;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Cyclic Nucleotide related
• Mol File: 37762-06-4.mol

Chemical Properties

• Melting Point: 237-238°C dec.
• Boiling Point: 406.3 °C at 760 mmHg
• Flash Point: 199.5 °C
• Appearance: white/solid
• Density: 1.48 g/cm³
• Vapor Pressure: 8.24E-07mmHg at 25°C
• Refractive Index: 1.718
• Storage Temp.: Store at RT
• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.11 mg/m
• PKA: 6.92±0.20(Predicted)
• CAS DataBase Reference: ZAPRINAST(CAS DataBase Reference)
• NIST Chemistry Reference: ZAPRINAST(37762-06-4)
• EPA Substance Registry System: ZAPRINAST(37762-06-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: XZ6157358
• Hazardous Substances Data: 37762-06-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Zaprinast is used as a cGMP phosphodiesterase inhibitor for its vasodilating, relaxant, and diuretic effects. It enhances the vasodilatory effects of nitric oxide in various vascular tissues by prolonging the cGMP-mediated activation of cGMP-dependent protein kinase, making it potentially useful in treating hypertension and congestive heart failure.
Used in Reproductive Biology Research:
Zaprinast is used as an inhibitor in the meiosis of oocytes by germinal vesicle breakdown (GVBD) assay, helping researchers understand its effects on oocyte development and meiosis.
Used in Retinal Cell Research:
Zaprinast is used to test the inhibitory effect on retinal cells through immunohistochemistry, providing insights into its potential applications in ophthalmology and vision research.
Used in Signal Transduction Research:
Zaprinast is used as a research tool to study the activation of the rat and human G protein-coupled receptor, GPR35, with EC50 values of 16 nM and 0.84 μM, respectively, contributing to the understanding of signal transduction pathways and their role in various cellular processes.

Biological Activity

Phosphodiesterase inhibitor, selective for PDE6, 5, 11 and 9 (IC 50 values are 0.15, 0.76, 12.0 and 29.0 μ M respectively).

Biochem/physiol Actions

Zaprinast insubstantially inhibits phosphodiesterase 10 and 11 (PDE10 and PDE11). It also exhibits vasodilating effects.

in vitro

zaprinast is a pde5 and pde6 inhibitor with inhibiting pde9 at moderately high concentrations (29 mm) [1]. indeed, it showed that inhibition of cgmp hydrolysis by infusion of zaprinast increases the effect of anp on natriuresis with no causing deleterious drops in blood pressure. because it was known that anp receptors is localized within the glomerulus and inner medullary collecting ducts, to determine the cellular localization of pde9 enzyme in kidney will be interesting. [2]. the enzyme displayed a high specificity for cgmp with binding sites for cgmp, and a sensitivity to zaprinast similar to smooth muscle pde5, resulting in both enzymes were named cgmp-pde. however, retinal cgmp-pde was first distinguished as photoreceptor cgmp-pde with being specifically distributed in the retina and having a higher vmax and km values than other cgmp-pdes and being modulated by g protein. [3].

IC 50

0.15, 0.76, 12.0 and 29.0 μm for pde6, 5, 11 and 9 respectively.

references

[1] christensen and torphy (1994) isozyme-selective phosphodiesterase inhibitors as antiasthmatic agents. annu.rep.med.chem. 29 185.[2] soderling sh, bayuga sj, beavo ja. identification and characterization of a novel family of cyclic nucleotide phosphodiesterases. j biol chem. 1998 jun 19; 273(25):15553-8.[3]. lugnier c. cyclic nucleotide phosphodiesterase (pde) superfamily: a new target for the development of specific therapeutic agents. pharmacol ther. 2006 mar; 109 (3):366-98. epub 2005 aug 15.

InChI:InChI=1/C13H13N5O2/c1-2-7-20-9-6-4-3-5-8(9)11-14-12-10(13(19)15-11)16-18-17-12/h3-6H,2,7H2,1H3,(H2,14,15,16,17,18,19)