P1726
4-Phenyl-3-furoxancarbonitrile
Synonym(s):
Furoxan, RVC-589
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About This Item
Empirical Formula (Hill Notation):
C9H5N3O2
Molecular Weight:
187.15
UNSPSC Code:
12352202
PubChem Substance ID:
MDL number:
InChI
1S/C9H5N3O2/c10-6-8-9(11-14-12(8)13)7-4-2-1-3-5-7/h1-5H
SMILES string
[O-][n+]1onc(-c2ccccc2)c1C#N
InChI key
PMYJGTWUVVVOFO-UHFFFAOYSA-N
assay
≥99% (TLC)
form
powder
solubility
ethanol: 25 mg/mL to clear, colorless
storage temp.
2-8°C
Biochem/physiol Actions
NO donor, mediated by thiol-containing cofactors, even synthetic exogenous compounds such as thiophenol. Activator of rat lung soluble guanylyl cyclase. Platelet aggregation inhibitor (IC50 = 200 nM).
signalword
Warning
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
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 Information
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S X Liu et al.
Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics, 13(2), 105-114 (1997-04-01)
It is known that NO is involved in the regulation of intraocular pressure (IOP) and retinal function recovery after ischemia. Thus, S-nitrosoglutathione (RVC-588) and 4-phenyl-3-furoxancarbonitrile (RVC-589) as NO donor and precursor, respectively, were studied in terms of their ability to
C Medana et al.
Journal of medicinal chemistry, 37(25), 4412-4416 (1994-12-09)
4-Phenyl-3-furoxancarbonitrile (2) affords nitric oxide under the action of thiol cofactors. Two principal products were isolated in the reaction with thiophenol: the phenylcyanoglyoxime (6) and 5-amino-3-phenyl-4-(phenylthio)isoxazole (7). Mechanisms which could account for the formation of these two products are discussed.
R Ferioli et al.
British journal of pharmacology, 114(4), 816-820 (1995-02-01)
1. The mechanism of action and biological activity of a series of R-substituted and di-R-substituted phenylfuroxans is reported. 2. Maximal potency as vasodilators on rabbit aortic rings, precontracted with noradrenaline (1 microM), was shown by phenyl-cyano isomers and by the
Yun Hua et al.
Assay and drug development technologies, 12(7), 395-418 (2014-09-03)
The androgen receptor-transcriptional intermediary factor 2 (AR-TIF2) positional protein-protein interaction (PPI) biosensor assay described herein combines physiologically relevant cell-based assays with the specificity of binding assays by incorporating structural information of AR and TIF2 functional domains along with intracellular targeting
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