Structure via PubChem · Public domain (PubChem)
zaprinast
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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, selective for the subtypes PDE5, PDE6, PDE9 and PDE11. IC50 values are 0.76, 0.15, 29.0, and 12.0 μM, respectively.
In the Vinony graph
Vinony's link graph records 101 inbound references to zaprinast, and connects out to Plasmodium falciparum, malaria and digital object identifier.
It is catalogued under topics including Abandoned drugs, Chembox image size set and ECHA InfoCard ID from Wikidata.
Vinony links it to 5 Wikipedia language editions.
Chemical data
- Formula
- C13H13N5O2
- Molecular weight
- 271.27 g/mol
- IUPAC name
- 5-(2-propoxyphenyl)-2,3-dihydrotriazolo[4,5-d]pyrimidin-7-one
- SMILES
- CCCOC1=CC=CC=C1C2=NC(=O)C3=NNNC3=N2
- InChIKey
- REZGGXNDEMKIQB-UHFFFAOYSA-N
- XLogP
- 2.2
- Polar surface area
- 87.4 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
939 papers- Zaprinast and avanafil increase the vascular endothelial growth factor, vitamin D(3), bone morphogenic proteins 4 and 7 levels in the kidney tissue of male rats applied the glucocorticoid.Archives of physiology and biochemistry · 2022
- Can zaprinast and avanafil induce the levels of angiogenesis, bone morphogenic protein 2, 4 and 7 in kidney of ovariectomised rats?Archives of physiology and biochemistry · 2022
- Phosphodiesterase 5 inhibitors and nitrergic transmission-from zaprinast to sildenafil.European journal of pharmacology · 2001
- Zaprinast activates MAPKs, NFκB, and Akt and induces the expressions of inflammatory genes in microglia.International immunopharmacology · 2012
- Zaprinast, a phosphodiesterase type-5 inhibitor, alters paced mating behavior in female rats.Physiology & behavior · 2009
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 271.106925
Show 3 more facts
- canonical SMILES
- CCCOC1=CC=CC=C1C2=NC(=O)C3=NNNC3=N2
- chemical formula
- C₁₃H₁₃N₅O₂
- subject has role
- phosphodiesterase inhibitor
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- 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, selective for the subtypes PDE5, PDE6, PDE9 and PDE11. IC50 values are 0.76, 0.15, 29.0, and 12.0 μM, respectively.
Zaprinast inhibits the growth of asexual blood-stage malaria parasites (P. falciparum) in vitro with an ED50 value of 35 μM, and inhibits PfPDE1, a P. falciparum cGMP-specific phosphodiesterase, with an IC50 value of 3.8 μM.
Excerpted from Wikipedia’s “zaprinast” article, available under the CC BY-SA 4.0 licence.