Nifuroxazide

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

What is the Nifuroxazide?

The molecule Nifuroxazide presents a molecular formula of C12H9N3O5 and its IUPAC name is 4-hydroxy-N-[(E)-(5-nitrofuran-2-yl)methylideneamino]benzamide.

Nifuroxazide (INN) is a nitrofuran derivative with antibacterial and antidiarrheal properties. It is marketed under various trade names, including Ercefuril, Enterofuril, and Furazolidone..

Nifuroxazide acts by inhibiting bacterial DNA replication and protein synthesis. It is active against a broad range of Gram-positive and Gram-negative bacteria..

Nifuroxazide is used for the treatment of diarrhea, dysentery, and enterocolitis. It is also used for the prevention of traveler's diarrhea..

Nifuroxazide is generally well-tolerated. The most common side effects are gastrointestinal in nature, such as nausea, vomiting, and abdominal pain..

Nifuroxazide should not be used in patients with a history of hypersensitivity to nitrofurans. It should also be used with caution in patients with renal impairment..

Nifuroxazide is a safe and effective medication for the treatment of diarrhea and other gastrointestinal infections. It is important to follow the instructions of your healthcare provider when taking this medication..

3D structure

Cartesian coordinates

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

2D drawing

 

Nifuroxazide YCWSUKQGVSGXJO-NTUHNPAUSA-N chemical compound 2D structure molecule svg
Nifuroxazide

 

Molecule descriptors

 
IUPAC name4-hydroxy-N-[(E)-(5-nitrofuran-2-yl)methylideneamino]benzamide
InChI codeInChI=1S/C12H9N3O5/c16-9-3-1-8(2-4-9)12(17)14-13-7-10-5-6-11(20-10)15(18)19/h1-7,16H,(H,14,17)/b13-7+
InChI KeyYCWSUKQGVSGXJO-NTUHNPAUSA-N
SMILESO=C(N/N=C/c1ccc([N+](=O)[O-])o1)c1ccc(O)cc1

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.

  • (Nitro-5' furfurylidene-2') hydroxy-4 benzhydrazide
  • 4-Dydroxy-N-[(E)-(5-nitro-2-furyl)methyleneamino]benzamide
  • 4-Hydroxy-N'-((5-nitrofuran-2-yl)methylene)benzohydrazide
  • 4-Hydroxy-N'-(5-nitrofurfuryliden)benzhydrazid
  • 4-hydroxy-N'-[(1E)-(5-nitro-2-furyl)methylene]benzohydrazide
  • 4-hydroxy-N'-[(E)-(5-nitrofuran-2-yl)methylidene]benzohydrazide
  • 4-hydroxy-N-[(E)-(5-nitro-2-furyl)methyleneamino]benzamide
  • 4-hydroxy-N-[(E)-(5-nitrofuran-2-yl)methylidene]benzenecarbohydrazonic acid
  • 4-hydroxy-N-[(E)-(5-nitrofuran-2-yl)methylideneamino]benzamide
  • 965-52-6
  • 965N526
  • A845610
  • AB00513861
  • AB00513861_02
  • AB00513861_03
  • AC-8713
  • AS-13310
  • BDBM50396177
  • BENZOIC ACID, p-HYDROXY-, (5-NITROFURFURYLIDENE)HYDRAZIDE
  • BIM-0014420.P001
  • BPBio1_000693
  • BRN 1352180
  • BSPBio_000629
  • Benzoic acid, 4-hydroxy-, 2-[(5-nitro-2-furanyl)methylene]hydrazide
  • Benzoic acid, 4-hydroxy-, [(1E)-(5-nitro-2-furanyl)methylene]hydrazide
  • CCG-213989
  • CCRIS 5490
  • CS-4918
  • D07111
  • DB13855
  • Diarlidan
  • Diaryl
  • Dicoferin
  • Ercefurol
  • Ercefuryl
  • HMS1569P11
  • HMS2096P11
  • HMS3713P11
  • HY-B1436
  • MFCD00079482
  • MLS000069620
  • NSC 759261
  • NSC-759261
  • NSC759261
  • Nifuroxazid
  • Nifuroxazida
  • Nifuroxazide
  • Nifuroxazide (INN)
  • Nifuroxazidum
  • Opera_ID_40
  • PM5LI0P38J
  • Pharmakon1600-01505788
  • Prestwick2_000555
  • Prestwick3_000555
  • Prestwick_874
  • R.C. 27-109
  • RC 27109
  • RC-27109
  • SBI-0014420.P002
  • SJ000287313
  • SMR000058185
  • STK091243
  • STL454990
  • W-100139
  • p-Hydroxybenzoic acid (5-nitrofurfurylidene)hydrazide
  • p-Hydroxybenzoic acid 5-nitrofurfurylidene hydrazide
  • s4182

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC7997719
  • UNII-PM5LI0P38J
  • AKOS000483758
  • BRD-K68188368-001-03-7
  • CHEMBL244888
  • CHEBI:94556
  • CHEBI:135136
  • EINECS 213-522-0
  • SCHEMBL542542
  • SCHEMBL543480
  • SCHEMBL14608895

Physico-Chemical properties

IUPAC name4-hydroxy-N-[(E)-(5-nitrofuran-2-yl)methylideneamino]benzamide
Molecular formulaC12H9N3O5
Molecular weight275.217
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity70.72
LogP2.6
Topological polar surface area120.7

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.