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Zaprinast

From Wikipedia, the free encyclopedia
Zaprinast
Names
IUPAC name
5-(2-Propoxyphenyl)-1H-[1,2,3]triazolo[4,5-d]pyrimidin-7(4H)-one
Other names
M&B 22,948
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.048.760Edit this at Wikidata
EC Number
  • 253-655-1
UNII
  • 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) checkY
    Key: REZGGXNDEMKIQB-UHFFFAOYSA-N checkY
  • O=C1C2=C(N=NN2)NC(C3=CC=CC=C3OCCC)=N1
Properties
C13H13N5O2
Molar mass271.280 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Zaprinast was an unsuccessful clinical drug candidate that was a precursor to the chemically relatedPDE5 inhibitors, such assildenafil (Viagra), which successfully reached the market. It is aphosphodiesterase inhibitor,[1] selective for the subtypesPDE5,PDE6,PDE9 andPDE11.IC50 values are 0.76, 0.15, 29.0, and 12.0μM, respectively.[2][3]

Zaprinast inhibits the growth of asexual blood-stagemalaria parasites (P. falciparum)in vitro with anED50 value of 35μM, and inhibits PfPDE1, aP. falciparum cGMP-specific phosphodiesterase, with an IC50 value of 3.8μM.[4]

Zaprinast has also been shown to activate the orphanG-protein coupled receptor known asGPR35, both in rats and humans,[5] and to inhibit the mitochondrialpyruvate carrier.[6]

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.S2CID 24513289.
  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.Bibcode:2006FEBSL.580.5003T.doi:10.1016/j.febslet.2006.08.015.PMID 16934253.S2CID 43142927.
  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.
  4. ^Keizo Yuasa; Fumika Mi-Ichi; Tamaki Kobayashi; Masaya Yamanouchi; Jun Kotera; Kiyoshi Kita; Kenji Omori (2005)."PfPDE1, a novel cGMP-specific phosphodiesterase from the human malaria parasite Plasmodium falciparum".Biochem. J.392 (Pt 1):221–9.doi:10.1042/BJ20050425.PMC 1317681.PMID 16038615.
  5. ^Yasuhito Taniguchi; Hiroko Tonai-Kachi; Katsuhiro Shinjo (2006). "Zaprinast, a well-known cyclic guanosine monophosphate-specific phosphodiesterase inhibitor, is an agonist for GPR35".FEBS Letters.580 (21):5003–5008.Bibcode:2006FEBSL.580.5003T.doi:10.1016/j.febslet.2006.08.015.PMID 16934253.S2CID 43142927.
  6. ^Jianhai Du; Whitney M Cleghorn; Laura Contreras; Ken Lindsay; Austin M Rountree; Andrei O Chertov; Sally J Turner; Ayse Sahaboglu; Jonathan Linton; Martin Sadilek; Jorgina Satrustegui; Ian R Sweet; Francois Paquet-Durand; James B Hurley (2013)."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):36129–36140.doi:10.1074/jbc.M113.507285.PMC 3861660.PMID 24187136.S2CID 9429684.
PDE1
PDE2
PDE3
PDE4
PDE5
PDE7
PDE9
PDE10
PDE11
Non-selective
Unsorted


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