Zaprinast

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Zaprinast
Zaprinast.svg
Identifiers
CAS number 37762-06-4 N
PubChem 5722
ChemSpider 5520 YesY
ChEMBL CHEMBL28079 YesY
Jmol-3D images Image 1
Properties
Molecular formula C13H13N5O2
Molar mass 271.27 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Zaprinast was an unsuccessful clinical drug candidate that was a precursor to the chemically related PDE5 inhibitors, such as sildenafil (Viagra), which successfully reached the market. It is a phosphodiesterase inhibitor,[1] selective for the subtypes PDE5, PDE6, PDE9 and PDE11. IC50 values are 0.76, 0.15, 29.0, and 12.0 μM, respectively.[2][3]

Zaprinast has also been shown to activate the orphan G-protein coupled receptor known as GPR35, both in rats and humans.[4] The clinical significance of this has yet to be determined.

References[edit]

  1. ^ Choi, SH; Choi, DH; Song, KS; Shin, KH; Chun, BG (2002). "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". Journal of neuroscience research 67 (3): 411–21. doi:10.1002/jnr.10102. PMID 11813247. 
  2. ^ Taniguchi, Y.; Tonaikachi, H.; Shinjo, K. (2006). "Zaprinast, a well-known cyclic guanosine monophosphate-specific phosphodiesterase inhibitor, is an agonist for GPR35". FEBS Letters 580 (21): 5003–5008. doi:10.1016/j.febslet.2006.08.015. PMID 16934253.  edit
  3. ^ Keswani, A. N.; Peyton, K. J.; Durante, W.; Schafer, A. I.; Tulis, D. A. (2009). "The Cyclic GMP Modulators YC-1 and Zaprinast Reduce Vessel Remodeling Through Antiproliferative and Proapoptotic Effects". Journal of Cardiovascular Pharmacology and Therapeutics 14 (2): 116–124. doi:10.1177/1074248409333266. PMC 2702762. PMID 19342499.  edit
  4. ^ Yasuhito Taniguchi, Hiroko Tonai-Kachi, Katsuhiro Shinjo (2006). "Zaprinast, a well-known cyclic guanosine monophosphate-specific phosphodiesterase inhibitor, is an agonist for GPR35". REBS Letters 580 (21): 5003–5008.