Avibactam

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

What is the Avibactam?

The molecule Avibactam presents a molecular formula of C7H11N3O6S and its IUPAC name is [(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate.

Avibactam is a new beta-lactamase inhibitor that is currently in development. This molecule was designed to improve the activity of currently available beta-lactam antibiotics against Gram-negative bacteria. In addition, avibactam has the potential to restore the activity of beta-lactam antibiotics against bacteria that have acquired resistance to these drugs..

The mechanism of action of avibactam is unique among beta-lactamase inhibitors. Avibactam binds to the active site of the beta-lactamase enzyme, preventing the enzyme from hydrolyzing the beta-lactam ring of the antibiotic. This results in the antibiotic being able to retain its full activity against the bacteria..

Avibactam is currently in clinical trials and is showing promise as a new tool for the treatment of Gram-negative infections. This molecule has the potential to restore the activity of beta-lactam antibiotics against bacteria that have acquired resistance to these drugs..

3D structure

Cartesian coordinates

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

2D drawing

 

Avibactam NDCUAPJVLWFHHB-UHNVWZDZSA-N chemical compound 2D structure molecule svg
Avibactam

 

Molecule descriptors

 
IUPAC name[(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate
InChI codeInChI=1S/C7H11N3O6S/c8-6(11)5-2-1-4-3-9(5)7(12)10(4)16-17(13,14)15/h4-5H,1-3H2,(H2,8,11)(H,13,14,15)/t4-,5+/m1/s1
InChI KeyNDCUAPJVLWFHHB-UHNVWZDZSA-N
SMILESNC(=O)[C@@H]1CC[C@@H]2CN1C(=O)N2OS(=O)(=O)O

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.

  • (1R,2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl hydrogen sulfate
  • (1R,2S,5R)-7-OXO-6-SULFOOXY-1,6-DIAZABICYCLO(3.2.1)OCTANE-2-CARBOXAMIDE
  • (2S,5R)-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
  • 06MFO7817I
  • 1,6-Diazabicyclo(3.2.1)octane-2-carboxamide, 7-oxo-6-(sulfooxy)-, (1R,2S,5R)-rel-
  • 1192500-31-4
  • 396731-14-9
  • 794508-22-8
  • AC-35749
  • AMY24028
  • AVE-1330A free acid
  • AVI
  • AVIBACTAM COMPONENT OF ZAVICEFTA
  • AVIBACTAM, (+/-)-
  • Avibactam
  • Avibactam (free acid)
  • Avibactam free acid
  • Avibactamfreeacid
  • BDBM50339145
  • CS-0593
  • DB09060
  • E80372
  • GTPL10761
  • HY-14879
  • NXL104
  • Nxl-104 free acid
  • Q15410251
  • SULFURIC ACID, MONO((1R,2S,5R)-2-(AMINOCARBONYL)-7-OXO-1,6-DIAZABICYCLO(3.2.1)OCT-6-YL) ESTER
  • SULFURIC ACID, MONO[(1R,2S,5R)-2-(AMINOCARBONYL)-7-OXO-1,6-DIAZABICYCLO[3.2.1]OCT-6-YL] ESTER
  • ZAVICEFTA COMPONENT AVIBACTAM
  • [(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate
  • trans-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3.2.1]octan-2-carboxamide

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC9302239
  • UNII-06MFO7817I
  • UNII-7352665165
  • DTXSID901026066
  • CHEMBL1689063
  • CHEBI:85984
  • SCHEMBL1666807

Physico-Chemical properties

IUPAC name[(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]octan-6-yl] hydrogen sulfate
Molecular formulaC7H11N3O6S
Molecular weight265.244
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity60.27
LogP0.1
Topological polar surface area138.6

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.