Zaprinast

Names

[ Name ]:
Zaprinast

[Synonym ]:
1H-1,2,3-triazolo[4,5-d]pyrimidin-7-ol, 5-(2-propoxyphenyl)-
2-(2-PROPYLOXYPHENYL)-8-AZAPURIN-6-ONE
5-(2-Propoxyphenyl)-1,4-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
2-o-propoxyphenyl-8-azapurin-6-one
EINECS 253-655-1
Potassium phosphate monobasic
Zaprinast
3,6-dihydro-5-(2-propoxyphenyl)
Phenylaza purinon
2-(2-Propoxyphenyl)-8-azahypoxanthine
MFCD00214073
5-(2-Propoxyphenyl)-2,3-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one, 3,4-dihydro-5-(2-propoxyphenyl)-
B 22,948
8-Aza-2-(2-propoxyphenyl)-6-purinone
5-(2-propoxyphenyl)-1H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ol
1,4-Dihydro-5-(2-propoxyphenyl)-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one
7H-1,2,3-Triazolo[4,5-d]pyrimidin-7-one, 1,4-dihydro-5-(2-propoxyphenyl)-
5-(2-Propoxyphenyl)-3,4-dihydro-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)pyrimidin-7-one
1,4-Dihydro-5-(2-propoxyphenyl)-1,2,3-triazolo[4,5-d]pyrimidin-7-one
7H-1,2,3-Triazolo[4,5-d]pyrimidin-7-one, 2,3-dihydro-5-(2-propoxyphenyl)-

Biological Activity

[Description]:

Zaprinast (M&B 22948) is an inhibitor of cGMP-selective Phosphodiesterases(PDEs)[1]. Zaprinast is a G protein-coupled receptor (GPR) 35 agonist which activates rat GPR35 strongly and activates human GPR35 moderately[2]. Zaprinast reduces vessel remodeling through antiproliferative and proapoptotic effects[3].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE)

Signaling Pathways >> GPCR/G Protein >> CXCR

Signaling Pathways >> Immunology/Inflammation >> CXCR

Research Areas >> Neurological Disease

[Target]

PDE[1], GPR35[2]

[References]

[1]. Choi SH , et al. Zaprinast, an inhibitor of cGMP-selective phosphodiesterases, enhances the secretion of TNF-alpha and IL-1beta and the expression of iNOS and MHC class II molecules in rat microglial cells. J Neurosci Res. 2002 Feb 1;67(3):411-21.

[2]. Taniguchi Y, et al. Zaprinast, a well-known cyclic guanosine monophosphate-specific phosphodiesterase inhibitor, is an agonist for GPR35. FEBS Lett. 2006 Sep 18;580(21):5003-8. Epub 2006 Aug 17.

[3]. Keswani AN , et al The cyclic GMP modulators YC-1 and zaprinast reduce vessel remodeling through antiproliferative and proapoptotic effects. J Cardiovasc Pharmacol Ther. 2009 Jun;14(2):116-24.

Chemical & Physical Properties

[ Density]:
1.484g/cm3

[ Boiling Point ]:
406.3±47.0 °C at 760 mmHg

[ Melting Point ]:
237-238ºC dec.

[ Molecular Formula ]:
C₁₃H₁₃N₅O₂

[ Molecular Weight ]:
271.275

[ Flash Point ]:
199.5±29.3 °C

[ Exact Mass ]:
271.106934

[ PSA ]:
96.55000

[ LogP ]:
0.17

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.719

[ Storage condition ]:
2-8℃

[ Water Solubility ]:
Soluble to 100 mM in DMSO

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26;S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
XZ6157358

Articles

Metabolomics analysis of metabolic effects of nicotinamide phosphoribosyltransferase (NAMPT) inhibition on human cancer cells.

PLoS ONE 9(12) , e114019, (2014)

Nicotinamide phosphoribosyltransferase (NAMPT) plays an important role in cellular bioenergetics. It is responsible for converting nicotinamide to nicotinamide adenine dinucleotide, an essential molec...

Inhibition of mitochondrial pyruvate transport by zaprinast causes massive accumulation of aspartate at the expense of glutamate in the retina.

J. Biol. Chem. 288(50) , 36129-40, (2013)

Transport of pyruvate into mitochondria by the mitochondrial pyruvate carrier is crucial for complete oxidation of glucose and for biosynthesis of amino acids and lipids. Zaprinast is a well known pho...

GPR35 activation reduces Ca2+ transients and contributes to the kynurenic acid-dependent reduction of synaptic activity at CA3-CA1 synapses.

PLoS ONE 8 , e82180, (2013)

Limited information is available on the brain expression and role of GPR35, a Gi/o coupled receptor activated by kynurenic acid (KYNA). In mouse cultured astrocytes, we detected GPR35 transcript using...

Related Compounds

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