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.
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.