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ZAPRINAST

Product Name
ZAPRINAST
CAS No.
37762-06-4
Chemical Name
ZAPRINAST
Synonyms
ZAPRINAST;M&B 22,948;M AND B 22948;M-EPSILON-TB22948;Phenylaza purinon;ZAPRINAST USP/EP/BP;Zaprinast (M&B 22948);3,6-dihydro-5-(2-propoxyphenyl)-;2-(o-Propoxyphenyl)-8-azapurin-6-one;8-Aza-2-(2-propoxyphenyl)-6-purinone
CBNumber
CB3215496
Molecular Formula
C13H13N5O2
Formula Weight
271.27
MOL File
37762-06-4.mol
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ZAPRINAST Property

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
CAS DataBase Reference
37762-06-4
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Z0878
Product name
Zaprinast
Purity
solid
Packaging
25mg
Price
$103
Updated
2024/03/01
Alfa Aesar
Product number
J63326
Product name
Zaprinast, 98+%
Packaging
10mg
Price
$62.65
Updated
2024/03/01
Alfa Aesar
Product number
J63326
Product name
Zaprinast, 98+%
Packaging
50mg
Price
$265.65
Updated
2024/03/01
Cayman Chemical
Product number
10010421
Product name
Zaprinast
Purity
≥98%
Packaging
10mg
Price
$28
Updated
2024/03/01
Cayman Chemical
Product number
10010421
Product name
Zaprinast
Purity
≥98%
Packaging
50mg
Price
$117
Updated
2024/03/01
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ZAPRINAST Chemical Properties,Usage,Production

Description

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.

Chemical Properties

Zaprinast is Yellow-Orange Crystalline Powder

Uses

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.

Uses

cGMP phosphodiesterase inhibitor

Uses

Zaprinast has been used to determine its inhibitory effect on the meiosis of oocytes by germinal vesicle breakdown (GVBD) assay and to test the inhibitory effect of it on the retinal cells by immunohistochemistry.

Definition

ChEBI: 5-(2-propoxyphenyl)-2,3-dihydrotriazolo[4,5-d]pyrimidin-7-one is a member of triazolopyrimidines.

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.

storage

Store at RT

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.

ZAPRINAST Preparation Products And Raw materials

Raw materials

Preparation Products

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ZAPRINAST Suppliers

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View Lastest Price from ZAPRINAST manufacturers

Dideu Industries Group Limited
Product
ZAPRINAST 37762-06-4
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons Min
Release date
2021-06-16

37762-06-4, ZAPRINASTRelated Search:

ZARDAVERINE RO 20-1724 ETAZOLATE BRL 50481 Vinpocetine ROLIPRAM Cilostazol (4S)-4-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]PYRROLIDIN-2-ONE CILOSTAMIDE 4-[[3,4-(METHYLENEDIOXY)BENZYL]AMINO]-6-CHLOROQUINAZOLINE EHNA HYDROCHLORIDE ZAPRINAST 2-ETHOXY-BENZAMIDINE 1H-[1,2,3]TRIAZOL-4-YLMETHYLAMINE HCL N-[(2-METHOXYPHENYL)METHYLENE]-N-METHYLAMINE 2-METHOXY-BENZAMIDINE HCL SALICYLALDEHYDE HYDRAZONE 2-PROPOXY-BENZAMIDINE

  • 1,4-DIHYDRO-5-[2-PROPOXYPHENYL]-7H-1,2,3-TRIAZOLO[4,5-D]PYRIMIDINE-7-ONE
  • 2-(o-Propoxyphenyl)-8-azapurin-6-one
  • 5-(2-propoxyphenyl)-2,3-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
  • 5-(2-propoxyphenyl)-2,3-dihydrotriazolo[4,5-d]pyrimidin-7-one
  • 3,6-dihydro-5-(2-propoxyphenyl)-
  • Zaprinast (M&B 22948)
  • Zaprinast - CAS 37762-06-4 - Calbiochem
  • 5-(2-Propoxyphenyl)-1H-[1,2,3]triazolo[4,5-d]pyrimidin-7(4H)-one
  • M AND B 22948
  • M-EPSILON-TB22948
  • 2-(2-PROPYLOXYPHENYL)-8-AZAPURIN-6-ONE
  • ZAPRINAST
  • 2-(2-Propoxyphenyl)-6-hydroxy-8-azapurine
  • 3,6-dihydro-5-(2-propoxyphenyl)-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one
  • 8-Aza-2-(2-propoxyphenyl)-6-purinone
  • M&B 22,948
  • 1,4-dihydro-5-(2-propoxyphenyl)-7h-1,2,3-triazolo(4,5-d)pyrimidin-7-one
  • 2-(2-Propoxyphenyl)-8-azahypoxanthine
  • Phenylaza purinon
  • 7H-1,2,3-Triazolo[4,5-d]pyrimidin-7-one, 3,6-dihydro-5-(2-propoxyphenyl)-
  • ZAPRINAST USP/EP/BP
  • 37762-06-4
  • C13H13N5O2
  • Phosphodiesterase Inhibitors
  • Cyclic Nucleotide Metabolism
  • G Proteins and Cyclic Nucleotides
  • Cell Biology
  • Cell Signaling and Neuroscience
  • BioChemical
  • All Inhibitors
  • Inhibitors
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Cyclic Nucleotide related