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

Canada 1 China 81 Germany 2 India 1 Japan 1 Switzerland 2 United Kingdom 7 United States 22 USA 1 Global 118

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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:

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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