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
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.32
Recommended Products
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
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
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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
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