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O3636

Sigma-Aldrich

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:
41443-28-1
Molecular Weight:
187.15
MDL number:
MFCD00792620
UNSPSC Code:
41106305
PubChem Substance ID:
24278054
NACRES:
NA.32

Assay

≥98% (TLC)

Quality Level

200

form

powder

color

pale yellow

solubility

ethanol: 1.2 mg/mL
DMSO: 5 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

O=C1ON=C2C=Nc3ccccc3N12

InChI

1S/C9H5N3O2/c13-9-12-7-4-2-1-3-6(7)10-5-8(12)11-14-9/h1-5H

InChI key

LZMHWZHOZLVYDL-UHFFFAOYSA-N

Gene Information

human ... NOS1(4842) , NOS2(4843) , NOS2B(201288) , NOS2C(645740) , NOS3(4846)

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.

Caution

Hygroscopic

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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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
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)
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)
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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