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Zaprinast

Cayman Chemical Item Number 10010421

2-(o-Propoxyphenyl)-8-azapurin-6-one; M&B 22,948 (CAS 37762-06-4)

Zaprinast (CAS 37762-06-4)

See more	Inhibitors (493) Nitric Oxide (101) Ophthalmology (61) Signal Transduction (314) Vascular Disease (103)

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.^1,2 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.² Zaprinast also activates both the rat and human G protein-coupled receptor, GPR35 with EC₅₀ values of 16 nM and 0.84 µM, respectively.³

1 Nakamizo, T., Kawamata, J., Yoshida, K., et al. Phosphodiesterase inhibitors are neuroprotective to cultured spinal motor neurons. J Neurosci Res 71 485-495 (2003).

2 Gibson, A. Phosphodiesterase 5 inhibitors and nitrergic transmission-from zaprinast to sildenafil. Eur J Pharmacol 411 1-10 (2001).

3 Taniguchi, Y., Tonai-Kachi, H., and Shinjo, K. Zaprinast, a well-known cyclic guanosine monophosphate-specific phosphodiesterase inhibitor, is an agonist for GPR35. FEBS Lett 580 5003-5008 (2006).

Synonyms	2-(o-Propoxyphenyl)-8-azapurin-6-one M&B 22,948
Formal Name	3,6-dihydro-5-(2-propoxyphenyl)-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one
CAS Number	37762-06-4
Molecular Formula	C₁₃H₁₃N₅O₂
Formula Weight	271.3
Formulation	A crystalline solid
Purity	≥98%
Stability	1 year
Storage	-20°C
Shipping	Room temperature in continental US; may vary elsewhere
SMILES	Copy SMILES to clipboard CCCOc1ccccc1c1[nH]c(=O)c2nn[nH]c2n1

Background Reading

Nakamizo, T., Kawamata, J., Yoshida, K., et al. Phosphodiesterase inhibitors are neuroprotective to cultured spinal motor neurons. J Neurosci Res 71 485-495 (2003).

Gibson, A. Phosphodiesterase 5 inhibitors and nitrergic transmission-from zaprinast to sildenafil. Eur J Pharmacol 411 1-10 (2001).

Taniguchi, Y., Tonai-Kachi, H., and Shinjo, K. Zaprinast, a well-known cyclic guanosine monophosphate-specific phosphodiesterase inhibitor, is an agonist for GPR35. FEBS Lett 580 5003-5008 (2006).

Size	Price	Quantity	Subtotal
10 mg	$21.00		$0.00
50 mg	$95.00		$0.00
100 mg	$168.00		$0.00
250 mg	$368.00		$0.00
Bulk	Contact
		Cart Total	$0.00

Pricing updated 2012-02-10. Prices are subject to change without notice.

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