3-cyano-4-phenyl-1,2,5-oxadiazol-2-ium-2-olate

• ChemBase ID: 155400
• Molecular Formular: C9H5N3O2
• Molecular Mass: 187.1549
• Monoisotopic Mass: 187.03817642
• SMILES: c1ccc(cc1)c1c([n+](on1)[O-])C#N
• Canonical SMILES: N#Cc1[n+]([O-])onc1c1ccccc1
• InChI: InChI=1S/C9H5N3O2/c10-6-8-9(11-14-12(8)13)7-4-2-1-3-5-7/h1-5H
• InChIKey: PMYJGTWUVVVOFO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-cyano-4-phenyl-1,2,5-oxadiazol-2-ium-2-olate
• IUPAC Traditional name: 3-cyano-4-phenyl-1,2,5-oxadiazol-2-ium-2-olate
• Synonyms: Furoxan, RVC-589; Phenyl-furazancarbonitrile 2-Oxide; 4-Phenyl-3-furoxancarbonitrile; Furoxan; RVC-589; 4-Phenyl-3-furoxancarbonitrile

Database IDs

• CAS Number: 125520-62-9
• MDL Number: MFCD00270898
• PubChem SID: 24278622; 162249538
• PubChem CID: 1756

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.2504
• LogD (pH = 7.4): 1.2504
• Log P: 1.2504
• Molar Refractivity: 69.8428 cm^3
• Polarizability: 18.737883 Å^3
• Polar Surface Area: 75.28 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Crystalline Solid
• Melting Point: 73-74°C

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C9H5N3O2

DETAILS

Sigma Aldrich - P1726

Biochem/physiol Actions
NO donor, mediated by thiol-containing cofactors, even synthetic exogenous compounds such as thiophenol.1 Activator of rat lung soluble guanylyl cyclase. Platelet aggregation inhibitor (IC50 = 200 nM).

Toronto Research Chemicals - P322500

Able to activate the soluble guanylate cyclase by releasing Nitric Oxide under the action of thiol cofactors. Also inhibits platelet aggregation.

REFERENCES

• Medana, C., et al.: J. Med. Chem., 37, 4412 (1994)
• Feridi, R., et al.: Br. J. Pharm., 114, 816 (1994)
• Liu, S.X., et al.: J. Ocul. Pharm. Ther., 13, 105 (1997)