Furazolidona

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Furazolidona are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Furazolidona?

The molecule Furazolidona presents a molecular formula of C8H7N3O5 and its IUPAC name is 3-[(Z)-(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one.

Furazolidone is a nitrofuran derivative with antiprotozoal and antibacterial activity. It was first synthesized in 1960 by a team of researchers at the Janssen Pharmaceutical Company. Furazolidone is structurally similar to nitrofurantoin, another nitrofuran derivative with similar activity. The mechanism of action of furazolidone is not fully understood, but it is thought to work by inhibiting the synthesis of nucleic acids and proteins in susceptible organisms. Furazolidone is active against a wide range of bacteria and protozoa, including Escherichia coli, Salmonella spp., Shigella spp., and Giardia lamblia. It is used to treat gastrointestinal and genitourinary infections caused by these organisms. Furazolidone exists in oral and topical formulations..

3D structure

Cartesian coordinates

Geometry of Furazolidona in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Furazolidona PLHJDBGFXBMTGZ-UITAMQMPSA-N chemical compound 2D structure molecule svg
Furazolidona

 

Molecule descriptors

 
IUPAC name3-[(Z)-(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one
InChI codeInChI=1S/C8H7N3O5/c12-8-10(3-4-15-8)9-5-6-1-2-7(16-6)11(13)14/h1-2,5H,3-4H2/b9-5-
InChI KeyPLHJDBGFXBMTGZ-UITAMQMPSA-N
SMILESO=C1OCCN1/N=C\c1ccc([N+](=O)[O-])o1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (E)-3-(((5-nitrofuran-2-yl)methylene)amino)oxazolidin-2-one
  • (E)-3-((5-nitrofuran-2-yl)methyleneamino)
  • (E)-3-((5-nitrofuran-2-yl)methyleneamino)oxazolidin-2-one
  • 67-45-8
  • C76126
  • Epitope ID:116184
  • FZL
  • Furanzolidone,(S)
  • Furazolidona
  • Furazolidonum
  • NCGC00016299-01
  • Q2467555
  • furazolidone

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC113418
  • CAS-67-45-8
  • CHEMBL1572167
  • CHEBI:5195

Physico-Chemical properties

IUPAC name3-[(Z)-(5-nitrofuran-2-yl)methylideneamino]-1,3-oxazolidin-2-one
Molecular formulaC8H7N3O5
Molecular weight225.158
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity56.97
LogP1.4
Topological polar surface area100.9

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.