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Z0878

Zaprinast

cGMP-specific phosphodiesterases V and VI inhibitor, solid

Synonym(s):

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

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25 MG

CZK 2,550.00

100 MG

CZK 7,301.50

CZK 2,550.00

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About This Item

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

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Product Name

Zaprinast, solid

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

SMILES string

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

form

solid

color

white

solubility

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

Quality Level

200

Gene Information

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

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This Item
T6154M228N149
Zaprinast solid

Sigma-Aldrich

Z0878

Zaprinast

Trazodone hydrochloride ≥99% (HPLC), powder

Sigma-Aldrich

T6154

Trazodone hydrochloride

MRS 1220 solid

Sigma-Aldrich

M228

MRS 1220

Nimodipine

Sigma-Aldrich

N149

Nimodipine

form

solid

form

powder

form

solid

form

powder

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

200

solubility

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

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble 23.3 mg/mL, methanol: soluble 25 mg/mL, clear, colorless, 0.1 M HCl: soluble 7.4 mg/mL, DMSO: soluble, H2O: soluble, hazy, colorless

solubility

DMSO: 2 mg/mL, 2-hydroxypropyl-β-cyclodextrin: insoluble, H2O: insoluble, ethanol: insoluble

solubility

methanol: 62.5 mg/mL, 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: insoluble, H2O: insoluble

color

white

color

-

color

white

color

off-white to yellow

Gene Information

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

Gene Information

human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2C(3358), SLC6A4(6532)

Gene Information

human ... ADORA3(140)
rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Gene Information

human ... ADORA3(140), CACNA1C(775), CACNA1D(776), CACNA1F(778), CACNA1S(779), CACNG1(786), NR3C2(4306)
rat ... Adora1(29290), Adora2a(25369)

Application

Zaprinast has been used to determine its inhibitory effect on the meiosis of oocytes by germinal vesicle breakdown (GVBD) assay [1] and to test the inhibitory effect of it on the retinal cells by immunohistochemistry.[2]

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).
Zaprinast insubstantially inhibits phosphodiesterase 10 and 11 (PDE10 and PDE11).[3] It also exhibits vasodilating effects.[2]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000458105
0000458105
0000458852
0000458852
0000436154

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Xinhua Zhang et al.
American journal of physiology. Endocrinology and metabolism, 302(2), E243-E253 (2011-10-27)
Testosterone (T) plays a permissive role in the development of benign prostatic hyperplasia (BPH), and phosphodiesterase 5 inhibitors (PDE5is) have been found to be effective for BPH and lower urinary tract symptoms (LUTS) in clinical trials. This study investigated the
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
Rick H Cote
Methods in molecular biology (Clifton, N.J.), 307, 141-154 (2005-07-01)
Of the 11 families of mammalian cyclic nucleotide phosphodiesterases (PDEs), 5 contain regulatory domains capable of binding cyclic guanosine 5'-monophosphate (cGMP). The best understood of the GAF-containing PDEs is the family of rod (PDE6R) and cone (PDE6C) photo receptor PDEs.
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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