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O3636

Sigma-Aldrich

1H-[1,2,4]Oxadiazolo[4,3-a]quinoxalin-1-one

powder

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Synonym(s):
ODQ
Empirical Formula (Hill Notation):
C9H5N3O2
CAS Number:
Molecular Weight:
187.15
MDL number:
PubChem Substance ID:
NACRES:
NA.32

assay

≥98% (TLC)

Quality Level

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

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Ammonium pyrrolidinedithiocarbamate ~99%

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Gene Information

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

Gene Information

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

Gene Information

human ... NOS1(4842), NOS2(4843), NOS2B(201288), NOS2C(645740), NOS3(4846), RELA(5970)

Gene Information

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

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

-

form

powder

form

solid

form

(powderor powder with lumps)

form

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

solubility

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

solubility

DMSO: soluble 30 mg/mL

solubility

water: 50 mg/mL, clear to very slightly hazy, colorless to faintly yellow

solubility

-

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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)
Nitric oxide and cGMP induce COX-2 expression and PGE2 production in human granulosa cells through CREB signaling pathway
Fang L, et al.
The Journal of Clinical Endocrinology and Metabolism, 100(2), E262-E269 (2015)
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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