5-(2-propoxyphenyl)-1H,4H,7H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one

• ChemBase ID: 104715
• Molecular Formular: C13H13N5O2
• Molecular Mass: 271.27462
• Monoisotopic Mass: 271.10692468
• SMILES: CCCOc1c(cccc1)c1nc(=O)c2c([nH]1)nn[nH]2
• Canonical SMILES: CCCOc1ccccc1c1nc(=O)c2c([nH]1)nn[nH]2
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(2-propoxyphenyl)-1H,4H,7H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one; 5-(2-propoxyphenyl)-3H,4H,7H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
• IUPAC Traditional name: zaprinast; 5-(2-propoxyphenyl)-3H,4H-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
• Synonyms: 1,4-Dihydro-5-[2-propoxyphenyl]-7H-1,2,3-triazolo[4,5d]pyrimidine-7-one; M & B 22948; ZAPRINAST; M&B 22,948; 1,4-Dihydro-5-(2-propoxyphenyl)-7H-1,2,3-triazolo(4,5-d)pyrimidin-7-one; Zaprinast

Database IDs

• CAS Number: 37762-06-4
• EC Number: 253-655-1
• MDL Number: MFCD00214073
• PubChem SID: 162093036; 24278072
• PubChem CID: 5722
• CHEMBL: 28079
• Chemspider ID: 5520
• Wikipedia Title: Zaprinast

CALCULATED PROPERTIES

• Acid pKa: 6.142505
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.1778634
• LogD (pH = 7.4): 0.67267376
• Log P: 2.2653344
• Molar Refractivity: 74.2885 cm^3
• Polarizability: 26.967182 Å^3
• Polar Surface Area: 92.26 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble0.11 mg/mL; DMSO: soluble10 mg/mL; H2O: insoluble
• Apperance: white solid

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... PDE2A(5138), PDE4A(5141), PDE4B(5142), PDE4D(5144)

Product Information

• Purity: 98%

DETAILS

MP Biomedicals - 02156931

Purity: 98%
Selective cGMP specific phosphodiesterase inhibitor.

Sigma Aldrich - Z0878

Biochem/physiol Actions
Selective inhibitor of cGMP-specific phosphodiesterases V and VI (PDE5/6) and an agonist at the G protein-coupled receptor 35 (GPR35).1

REFERENCES

• Gillespie, P.G., et al., Mol. Pharmacol. , 36 : 773, (1989).
• Burns, F., et al., Biochem. J. , 238 : 487, (1992).