ODQ

Product NameODQ
CAS41443-28-1
MFC9H5N3O2
MW187.15
EINECS
MOL File41443-28-1.mol

Chemical Properties

Melting point	160-170 °C
Boiling point	321.89°C (rough estimate)
Density	1.3753 (rough estimate)
refractive index	1.6500 (estimate)
RTECS	RO0913150
storage temp.	2-8°C
solubility	ethanol: 1.2 mg/mL
form	powder
pka	0.94±0.20(Predicted)
color	pale yellow
Stability	Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months.
InChI	1S/C9H5N3O2/c13-9-12-7-4-2-1-3-6(7)10-5-8(12)11-14-9/h1-5H
InChIKey	LZMHWZHOZLVYDL-UHFFFAOYSA-N
SMILES	[n]21c(n[o][c]2=O)cnc3c1cccc3
CAS DataBase Reference	41443-28-1(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36
WGK Germany	3
HS Code	29349990
Storage Class	11 - Combustible Solids

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English

Usage And Synthesis

Description

ODQ (41443-28-1) is a potent and selective inhibitor of soluble guanylyl cyclase (sGC),IC50= 20 nM).1 ODQ acts via competition with NO for the heme site of sGC where it binds irreversibly.2ODQ does not inhibit NO-mediated macrophage toxicity, an activity that is unrelated to cGMP nor does it inhibit particulate GC.1ODQ is an extremely useful tool to explore the involvement of the NO-cGMP pathway in cellular signaling and physiologic processes.3-5

Chemical Properties

ODQ is off-white to yellow powder

Uses

ODQ is a selective and potent sGC (soluble guanylyl cyclase) inhibitor.

Uses

1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one inhibits neurite outgrowth and causes neurite retraction in PC12 cells independently of soluble guanylyl cyclase.

Definition

ChEBI: 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one is a member of the class of oxadiazoloquinoxalines that is 1H-[1,2,4]oxadiazolo[4,3-a]quinoxaline substituted at position 1 by an oxo group. It has a role as an EC 4.6.1.2 (guanylate cyclase) inhibitor.

Biological Activity

ODQ is a potent and selective inhibitor of NO-sensitive guanylyl cyclase.

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.

storage

+4°C

References

[1] J GARTHWAITE. Potent and selective inhibition of nitric oxide-sensitive guanylyl cyclase by 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one.[J]. Molecular Pharmacology, 1995, 48 2: 184-188.
[2] A SCHRAMMEL. Characterization of 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one as a heme-site inhibitor of nitric oxide-sensitive guanylyl cyclase.[J]. Molecular Pharmacology, 1996, 50 1: 1-5.
[3] A G ESTÉVEZ. Nitric oxide-dependent production of cGMP supports the survival of rat embryonic motor neurons cultured with brain-derived neurotrophic factor.[J]. Journal of Neuroscience, 1998, 18 10: 3708-3714.
[4] G VANDECASTEELE R F T Eschenhagen. Role of the NO-cGMP pathway in the muscarinic regulation of the L-type Ca2+ current in human atrial myocytes.[J]. Journal of Physiology-London, 1998, 506 ( Pt 3): 653-663. DOI:10.1111/j.1469-7793.1998.653bv.x
[5] M C MARTINS-PINGE O U L G C Araújo. Nitric oxide-dependent guanylyl cyclase participates in the glutamatergic neurotransmission within the rostral ventrolateral medulla of awake rats.[J]. Hypertension, 1999, 34 4 Pt 2: 748-751. DOI:10.1161/01.hyp.34.4.748

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