Cefacetrile

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

What is the Cefacetrile?

The molecule Cefacetrile presents a molecular formula of C9H14N4O5 and its IUPAC name is (6R,7R)-3-(acetyloxymethyl)-7-[(2-cyanoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

Cefacetrile (also known as cefaclor) is a cephalosporin antibiotic. It is structurally similar to cephalexin and cefadroxil, and has a similar mechanism of action. Cefacetrile is active against a wide range of Gram-positive and Gram-negative bacteria..

Cefacetrile was first isolated in 1959 from a culture of Streptomyces cattleya. It was introduced into clinical use in the 1960s..

Cefacetrile is well absorbed from the gastrointestinal tract and is widely distributed throughout the body. It is excreted unchanged in the urine..

Cefacetrile is indicated for the treatment of a variety of bacterial infections, including upper respiratory tract infections, skin and soft tissue infections, and urinary tract infections. It is generally well tolerated, with the most common side effects being gastrointestinal upset and allergic reactions..

Cefacetrile is a safe and effective antibiotic for the treatment of a variety of bacterial infections. It is generally well tolerated with few side effects..

3D structure

Cartesian coordinates

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

2D drawing

 

Cefacetrile RTRQQBHATOEIAF-UUOKFMHZSA-N chemical compound 2D structure molecule svg
Cefacetrile

 

Molecule descriptors

 
IUPAC name(6R,7R)-3-(acetyloxymethyl)-7-[(2-cyanoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChI codeInChI=1S/C9H14N4O5/c10-7-4(8(11)17)12-2-13(7)9-6(16)5(15)3(1-14)18-9/h2-3,5-6,9,14-16H,1,10H2,(H2,11,17)/t3-,5-,6-,9-/m1/s1
InChI KeyRTRQQBHATOEIAF-UUOKFMHZSA-N
SMILESNC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1N

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.

  • (6R,7R)-3-(Acetoxymethyl)-7-(2-cyanoacetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • (6R,7R)-3-(Acetoxymethyl)-7-(2-cyanoacetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid
  • (6R,7R)-3-(acetyloxymethyl)-7-[(2-cyanoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • (6R,7R)-3-Acetoxymethyl-7-(2-cyanacetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure
  • (6R,7R)-3-[(acetyloxy)methyl]-7-(2-cyanoacetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • (6R,7R)-3-[(acetyloxy)methyl]-7-[(cyanoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • 10206-21-0
  • 2,4,6-TRIMETHOXYCINNAMICACID
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 3-[(acetyloxy)methyl]-7-[(2-cyanoacetyl)amino]-8-oxo-, (6R,7R)-
  • 7-(2-Cyanacetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carboxylat acetat (ester)
  • 7-Cyanacetylamino-cephalosporansaeure
  • CS-0017597
  • Cefacetril
  • Cefacetrile
  • Cefacetrile (INN)
  • Cefacetrilo
  • Cefacetrilum
  • Celospor
  • Cephacetrile
  • D07629
  • DB01414
  • FDM21QQ344
  • GTPL12192
  • HY-A0253
  • J-000558
  • NCGC00510891-01
  • Q4919176
  • Vetrimast
  • cephacetril

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3830496
  • UNII-FDM21QQ344
  • AKOS030240997
  • DTXSID0022779
  • CHEMBL2110602
  • CHEBI:135437
  • EINECS 233-508-8
  • SCHEMBL141792

Physico-Chemical properties

IUPAC name(6R,7R)-3-(acetyloxymethyl)-7-[(2-cyanoacetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Molecular formulaC9H14N4O5
Molecular weight258.231
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity57.67
LogP-1.5
Topological polar surface area156.9

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.