Compound: zaprinast
SMILES: O=c1nc([nH]c2c1[nH]nn2)-c3c(OCCC)cccc3
InChIKey: REZGGXNDEMKIQB-UHFFFAOYSA-N
Synonyms: zaprinast, 37762-06-4, Zaprinastum, M&B 22948, M&B-22948, NSC-757885, DTXSID8045224, GXT25D5DS0, 2-o-Propoxyphenyl-8-azapurine-6-one, DTXCID6025224, 2-(2-propoxyphenyl)-8-azapurin-6-one, 5-(2-propoxyphenyl)-2,3-dihydrotriazolo(4,5-e)pyrimidin-7-one, 5-(2-propoxyphenyl)-2,3-dihydrotriazolo[4,5-e]pyrimidin-7-one, RefChem:904807, 253-655-1, 2-(o-Propoxyphenyl)-8-azapurin-6-one, 5-(2-Propoxyphenyl)-1H-[1,2,3]triazolo[4,5-d]pyrimidin-7(4H)-one, Tocris-0947, 1,4-Dihydro-5-(2-propoxyphenyl)-7H-1,2,3-triazolo(4,5-d)pyrimidin-7-one, NCGC00016105-03, CAS-37762-06-4, 3,6-dihydro-5-(2-propoxyphenyl)-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one, 1110670-37-5, 5-(2-propoxyphenyl)-2,6-dihydrotriazolo[4,5-d]pyrimidin-7-one, Zaprinastum [INN-Latin], 1,4-Dihydro-5-(2-propoxyphenyl)-7H-1,2,3-triazolo[4,5-d]pyrimidin-7-one, M&B 22,948, M and B 22948, 8-Aza-2-(2-propoxyphenyl)-6-purinone, Zaprinast [INN:BAN], SR-01000075536, EINECS 253-655-1, UNII-GXT25D5DS0, Zaprinast?, Zaprinast, solid, Prestwick_655, 2-o-Propoxyphenyl-8-azapurin-6-on, MFCD00214073, Spectrum_001265, ZAPRINAST [INN], Prestwick0_000335, Prestwick1_000335, Prestwick2_000335, Prestwick3_000335, Spectrum2_001447, Spectrum3_000933, Spectrum4_001032, Spectrum5_001023, Lopac-Z-0878, 3,6-Dihydro-5-(o-propoxyphenyl)-7H-v-triazolo(4,5-d)pyrimidin-7-one, ZAPRINAST [MART.], 1,4-Dihydro-5-(2-propoxyphenyl)-7H-1,2,3-triazolo[4,5-d]pyrimidine-7-one, 3,6-Dihydro-5-(2-propoxyphenyl)-7H-(1,2,3)truaziki(4,5-d)pyrimidin-7-on, A1IL3, Lopac0_001240, SCHEMBL50328, SCHEMBL50329, SCHEMBL50330, BSPBio_000369, BSPBio_001348, KBioGR_001583, KBioSS_001745, MLS000859963, CHEMBL28079, DivK1c_000584, SPECTRUM1501199, SPBio_001313, SPBio_002290, Zaprinast (M B 22948), BPBio1_000407, GTPL2919, orb1306414, SCHEMBL6374345, SCHEMBL6913739, 5-(2-propoxyphenyl)-2H-triazolo[4,5-d]pyrimidin-7-ol, SCHEMBL30276335, SCHEMBL30713719, BCBcMAP01_000103, BDBM14363, CHEBI:92215, HMS501N06, KBio1_000584, KBio2_001745, KBio2_004313, KBio2_006881, KBio3_001966, NINDS_000584, GLXC-06862, HMS1569C11, HMS1791D10, HMS1921P15, HMS1989D10, HMS2090L04, HMS2096C11, HMS2235N23, HMS3263H22, HMS3267G07, HMS3370J04, HMS3402D10, HMS3411J20, HMS3675J20, HMS3713C11, Pharmakon1600-01501199, 5-(2-propoxyphenyl)-2,3-dihydrotriazolo[4,5-d]pyrimidin-7-one, HY-B1816, Tox21_110306, Tox21_501240, 6,7-Dihydro-5-(2-propoxyphenyl)-1H-triazolo(4,5-d)pyrimidin-7-on, BDBM50612246, CCG-39177, EX-A16639, NSC757885, 1,4-Dihydro-5-(2-propoxyphenyl)-1,2,3-triazolo(4,5-d)pyrimidin-7-one, 6,7-Dihydro-5-(2-propoxyphenyl)-1H-triazolo(4,5-d)pyrimidin-7-on [IUPAC], AKOS024458708, AKOS027446368, Tox21_110306_1, 2-(2-propoxyphenyl)-8-azahypoxanthine, CCG-205314, CCG-220335, CCG-222544, FZ28754, LP01240, NSC 757885, SDCCGSBI-0051207.P004, 7H-1,2,3-Triazolo(4,5-d)pyrimidin-7-one, 1,4-dihydro-5-(2-propoxyphenyl)-, IDI1_000584, SMP1_000321, NCGC00016105-01, NCGC00016105-02, NCGC00016105-04, NCGC00016105-05, NCGC00016105-08, NCGC00024894-01, NCGC00024894-02, NCGC00024894-03, NCGC00024894-04, NCGC00024894-08, NCGC00094481-01, NCGC00094481-02, NCGC00261925-01, DA-79072, MS-23838, SMR000326822, SBI-0051207.P002, CS-0013862, EU-0101240, NS00015865, M02689, Z 0878, AB00052245_02, SR-01000597480, Q6592076, SR-01000075536-1, SR-01000075536-4, SR-01000075536-5, SR-01000597480-1, BRD-K12516989-001-01-9, BRD-K16542329-001-05-1, BRD-K16542329-001-08-5, BRD-K16542329-001-13-5, BRD-K16542329-001-14-3, 5-(2-propoxyphenyl)-3,6-dihydrotriazolo[4,5-d]pyrimidin-7-one, 5-(2-Propoxy-phenyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one, 5-(2-propoxyphenyl)-2H,3H,7H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one, 3-(2-propoxyphenyl)-2,4,7,8,9-pentazabicyclo[4.3.0]nona-1,3,6-trien-5-one, 5-(2-propoxyphenyl)-1,4-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one, 5-(2-Propoxyphenyl)-3,6-dihydro-7H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one, 7H-1,2,3-Triazolo[4,5-d]pyrimidin-7-one, 2,3-dihydro-5-(2-propoxyphenyl)-, 7H-1,2,3-Triazolo[4,5-d]pyrimidin-7-one,2,3-dihydro-5-(2-propoxyphenyl)-
Theoretical properties:
molecular_formula: C13H13N5O2
molecular_weight: 271.27 g/mol
exact_mass: 271.10692467 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 4
heavy_atom_count: 20
topological_polar_surface_area: 92.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 31.4 [ug/mL] (The mean of the results at pH 7.4)
Descriptions:
pubchem: 5-(2-propoxyphenyl)-2,3-dihydrotriazolo[4,5-d]pyrimidin-7-one is a member of triazolopyrimidines.
chembl: ZAPRINAST is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: 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.
Zaprinast has also been shown to activate the orphan G-protein coupled receptor known as GPR35, both in rats and humans, and to inhibit the mitochondrial pyruvate carrier.