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Z0878

Sigma-Aldrich

Zaprinast

solid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C13H13N5O2
CAS Number:
37762-06-4
Molecular Weight:
271.27
EC Number:
253-655-1
MDL number:
MFCD00214073
UNSPSC Code:
12352202
PubChem Substance ID:
24278072
NACRES:
NA.77

form

solid

Quality Level

200

color

white

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.11 mg/mL
DMSO: 10 mg/mL
H2O: insoluble

SMILES string

CCCOc1ccccc1C2=NC(=O)c3nn[nH]c3N2

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)

InChI key

REZGGXNDEMKIQB-UHFFFAOYSA-N

Gene Information

human ... PDE2A(5138) , PDE4A(5141) , PDE4B(5142) , PDE4D(5144)

Application

Zaprinast has been used to determine its inhibitory effect on the meiosis of oocytes by germinal vesicle breakdown (GVBD) assay and to test the inhibitory effect of it on the retinal cells by immunohistochemistry.

Biochem/physiol Actions

Zaprinast insubstantially inhibits phosphodiesterase 10 and 11 (PDE10 and PDE11). It also exhibits vasodilating effects.
Selective inhibitor of cGMP-specific phosphodiesterases V and VI (PDE5/6) and an agonist at the G protein-coupled receptor 35 (GPR35).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Cristina Cosi et al.
Neuropharmacology, 60(7-8), 1227-1231 (2010-11-30)
G-protein coupled receptor 35 (GPR35) is a former "orphan receptor" expressed in brain and activated by either kynurenic acid or zaprinast. While zaprinast has been studied as a phosphodiesterase inhibitor, kynurenic acid (KYNA) is a tryptophan metabolite and has been
Barbara Picconi et al.
Brain : a journal of neurology, 134(Pt 2), 375-387 (2010-12-25)
The aim of the present study was to evaluate the role of the nitric oxide/cyclic guanosine monophosphate pathway in corticostriatal long-term depression induction in a model of levodopa-induced dyskinesia in experimental parkinsonism. Moreover, we have also analysed the possibility of
Selective pulmonary vasodilation induced by aerosolized zaprinast
Ichinose F, et al.
Anesthesiology, 88(2), 410-416 (1998)
P Calabresi et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 19(7), 2489-2499 (1999-03-23)
High-frequency stimulation (HFS) of corticostriatal glutamatergic fibers induces long-term depression (LTD) of excitatory synaptic potentials recorded from striatal spiny neurons. This form of LTD can be mimicked by zaprinast, a selective inhibitor of cGMP phosphodiesterases (PDEs). Biochemical analysis shows that
Resumption of meiosis induced by meiosis-activating sterol has a different signal transduction pathway than spontaneous resumption of meiosis in denuded mouse oocytes cultured in vitro
Faerge I, et al.
Biology of Reproduction, 65(6), 1751-1758 (2001)
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