O3636
1H-[1,2,4]Oxadiazolo[4,3-a]quinoxalin-1-one
powder
Synonym(s):
ODQ
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About This Item
Empirical Formula (Hill Notation):
C9H5N3O2
CAS Number:
Molecular Weight:
187.15
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
41106305
MDL number:
InChI
1S/C9H5N3O2/c13-9-12-7-4-2-1-3-6(7)10-5-8(12)11-14-9/h1-5H
SMILES string
O=C1ON=C2C=Nc3ccccc3N12
InChI key
LZMHWZHOZLVYDL-UHFFFAOYSA-N
assay
≥98% (TLC)
form
powder
color
pale yellow
solubility
ethanol: 1.2 mg/mL, DMSO: 5 mg/mL, H2O: insoluble
storage temp.
2-8°C
Quality Level
Gene Information
human ... NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846)
Related Categories
Application
1H-[1,2,4]Oxadiazolo[4,3-a]quinoxalin-1-one has been used as a oxidising agent for affinity selection-mass spectrometry (AS-MS) compound binding assay, as a soluble guanylate cyclase (sGC) inhibitor to inhibit S-nitroso-N-acetyl-DL-penicillamine (SNAP)-induced cGMP production.
Biochem/physiol Actions
H-[1,2,4]Oxadiazolo[4,3-a]quinoxalin-1-one (ODQ) non competitively inhibits the action of nitric oxide-sensitive guanylyl cyclase and results in a supposedly irreversible oxidation of the prosthetic heme group. ODQ has been used to study the role of cyclic guanosine monophosphate (cGMP) pathway in nitric oxide (NO) signal transduction.
Selective inhibitor of nitric oxide-sensitive guanylyl cyclase.
Disclaimer
Hygroscopic
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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Yayoi Shiokawa et al.
Planta medica, 85(13), 1080-1087 (2019-07-26)
Although Acanthopanax senticosus root extract (ASRE), a functional food used in Japan, improves peripheral blood circulation and exerts vasorelaxant effects in rats under healthy conditions, the underlying mechanisms currently remain unclear. Therefore, we investigated the mechanisms responsible for ASRE-induced relaxation
Potent and selective inhibition of nitric oxide-sensitive guanylyl cyclase by 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one.
Garthwaite J
Molecular Pharmacology, 48(2), 184-188 (1995)
The role of nitric oxide during embryonic epidermis development of Xenopus laevis
Tomankova S, et al.
Biology Open, 6(6), 862-871 (2017)
A Novel Selective Soluble Guanylate Cyclase Activator, MGV354, Lowers Intraocular Pressure in Preclinical Models, Following Topical Ocular Dosing
Prasanna G, et al.
Investigative Ophthalmology & Visual Science, 59(5), 1704-1716 (2018)
Characterization of 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one as a heme-site inhibitor of nitric oxide-sensitive guanylyl cyclase.
Schrammel A
Molecular Pharmacology, 50(1), 1-5 (1996)
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