(R)-nadifloxacin

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

What is the (R)-nadifloxacin?

The molecule (R)-nadifloxacin presents a molecular formula of C19H21FN2O4 and its IUPAC name is (12R)-7-fluoro-8-(4-hydroxypiperidin-1-yl)-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylic acid.

R-nadifloxacin is a fluoroquinolone antibiotic. It is the R-enantiomer of nadifloxacin..

Fluoroquinolones are a class of antibiotics that are particularly effective against Gram-negative bacteria. They work by inhibiting the bacterial enzyme DNA gyrase, which is responsible for unwinding and replicating the double-stranded DNA in bacteria..

R-nadifloxacin is active against a wide range of Gram-negative bacteria, including Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, and Pseudomonas aeruginosa. It is also active against some Gram-positive bacteria, such as Staphylococcus aureus and Streptococcus pneumoniae..

R-nadifloxacin exists as a 0.3% ophthalmic solution for the treatment of bacterial conjunctivitis. It can be found as a 0.4% intravaginal cream for the treatment of bacterial vaginosis..

R-nadifloxacin is generally well-tolerated. The most common side effects are eye irritation and vaginal burning and itching..

R-nadifloxacin is a safe and effective antibiotic for the treatment of bacterial infections. It has a wide range of activity against both Gram-positive and Gram-negative bacteria. It is well-tolerated and has a low incidence of side effects..

3D structure

Cartesian coordinates

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

2D drawing

 

(R)-nadifloxacin JYJTVFIEFKZWCJ-SNVBAGLBSA-N chemical compound 2D structure molecule svg
(R)-nadifloxacin

 

Molecule descriptors

 
IUPAC name(12R)-7-fluoro-8-(4-hydroxypiperidin-1-yl)-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylic acid
InChI codeInChI=1S/C19H21FN2O4/c1-10-2-3-12-16-13(18(24)14(19(25)26)9-22(10)16)8-15(20)17(12)21-6-4-11(23)5-7-21/h8-11,23H,2-7H2,1H3,(H,25,26)/t10-/m1/s1
InChI KeyJYJTVFIEFKZWCJ-SNVBAGLBSA-N
SMILESC[C@@H]1CCc2c(N3CCC(O)CC3)c(F)cc3c(=O)c(C(=O)O)cn1c23

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.

  • (5R)-9-fluoro-8-(4-hydroxypiperidin-1-yl)-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid
  • (R)-(+)-Nadifloxacin
  • (R)-nadifloxacin
  • 160961-35-3
  • Q27117309
  • R-(+)-Nadifloxacin
  • R-NDFX
  • R-Nadifloxacin

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3794622
  • AKOS015896496
  • DTXSID80167044
  • CHEBI:37907
  • SCHEMBL3818938

Physico-Chemical properties

IUPAC name(12R)-7-fluoro-8-(4-hydroxypiperidin-1-yl)-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylic acid
Molecular formulaC19H21FN2O4
Molecular weight360.379
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity99.46
LogP2.4
Topological polar surface area82.8

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.