Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

P1726

Sigma-Aldrich

4-Phenyl-3-furoxancarbonitrile

Synonym(s):

Furoxan, RVC-589

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C9H5N3O2
Molecular Weight:
187.15
MDL number:
MFCD00270898
UNSPSC Code:
12352202
PubChem Substance ID:
24278622

Assay

≥99% (TLC)

form

powder

solubility

ethanol: 25 mg/mL to clear, colorless

storage temp.

2-8°C

SMILES string

[O-][n+]1onc(-c2ccccc2)c1C#N

InChI

1S/C9H5N3O2/c10-6-8-9(11-14-12(8)13)7-4-2-1-3-5-7/h1-5H

InChI key

PMYJGTWUVVVOFO-UHFFFAOYSA-N

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).

Pictograms

Exclamation mark
GHS07

Signal Word

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 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service