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Merck

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

Key Documents

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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

200

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

O3636-VAR: + O3636-25MG-PW: + O3636-5MG: + O3636-BULK: + O3636-5MG-PW: + O3636-25MG:

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Certificates of Analysis (COA)

Lot/Batch Number
079M4142V
088M4091V
13180318
038M4021V
13170801

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Lineu Baldissera et al.
Pulmonary pharmacology & therapeutics, 41, 86-95 (2016-11-07)
Activators of soluble guanylyl cyclase (sGC) act preferentially in conditions of enzyme oxidation or haem group removal. This study was designed to investigate the effects of the sGC activator BAY 60-2770 in murine airways inflammation and human eosinophil chemotaxis. C57Bl/6
Diana Braun et al.
Frontiers in physiology, 9, 480-480 (2018-05-19)
Ischemia/reperfusion injury holds a key position in many pathological conditions such as acute kidney injury and in the transition to chronic stages of renal damage. We hypothesized that besides a reported disproportional activation of vasoconstrictor response, hypoxia/reoxygenation (H/R) adversely affects
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)
J Garthwaite et al.
Molecular pharmacology, 48(2), 184-188 (1995-08-01)
In brain and other tissues, nitric oxide (NO) operates as a diffusible second messenger that stimulates the soluble form of the guanylyl cylase enzyme and so elicits an accumulation of cGMP in target cells. Inhibitors of NO synthesis have been
Serena Materazzi et al.
Microvascular research, 109, 38-44 (2016-11-08)
The role of endogenous H2S has been highlighted as a gaseous transmitter. The vascular smooth muscle inhibitory effects of H2S have been characterized in isolated aorta and mesenteric arteries in rats and mice. Our study was aimed at investigating the
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