Zaprinast

• CAT Number: R000561
• CAS Number: 37762-06-4
• Molecular Formula: C13H13N5O2
• Molecular Weight: 271.28
• Purity: ≥95%
• Synonyms: 3,6-dihydro-5-(2-propoxyphenyl)-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]pyrimidine-7-one; 8-Aza-2-(2-propoxyphenyl)-6-purinone; M&B 22,948
• Target: GPR35
• Solubility: Soluble in DMSO > 10 mM
• Storage: Store at RT
• IUPAC Name: 5-(2-propoxyphenyl)-2,3-dihydrotriazolo[4,5-d]pyrimidin-7-one
• InChI: InChI=1S/C13H13N5O2/c1-2-7-20-9-6-4-3-5-8(9)11-14-12-10(13(19)15-11)16-18-17-12/h3-6H,2,7H2,1H3,(H2,14,15,16,17,18,19)
• InChIKey: REZGGXNDEMKIQB-UHFFFAOYSA-N
• SMILES: CCCOC1=CC=CC=C1C2=NC(=O)C3=NNNC3=N2

Zaprinast (CAS 37762-06-4) was an unsuccessful clinical drug candidate that was a precursor to the chemically related PDE5 inhibitors. It is a phosphodiesterase inhibitor, selective for the subtypes PDE5, PDE6, PDE9, and PDE11. IC50 values are 0.76, 0.15, 29.0, and 12.0 μM, respectively. Zaprinast has also been shown to activate the orphan G-protein coupled receptor known as GPR35, both in rats and humans, however, the clinical significance of this has yet to be determined.

Reference

1.Choi, Sang‐Hyun, et al. "Zaprinast, an inhibitor of cGMP‐selective phosphodiesterases, enhances the secretion of TNF‐α and IL‐1β and the expression of iNOS and MHC class II molecules in rat microglial cells." Journal of neuroscience research 67.3 (2002): 411-421.
2.Taniguchi, Yasuhito, Hiroko Tonai-Kachi, and Katsuhiro Shinjo. "Zaprinast, a well-known cyclic guanosine monophosphate-specific phosphodiesterase inhibitor, is an agonist for GPR35." FEBS letters 580.21 (2006): 5003-5008.
3.Keswani, Amit N., et al. "The cyclic GMP modulators YC-1 and zaprinast reduce vessel remodeling through antiproliferative and proapoptotic effects." Journal of cardiovascular pharmacology and therapeutics 14.2 (2009): 116-124.