(R)-Grepafloxacin

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

What is the (R)-Grepafloxacin?

The molecule (R)-Grepafloxacin presents a molecular formula of C19H22FN3O3 and its IUPAC name is 1-cyclopropyl-6-fluoro-5-methyl-7-[(3R)-3-methylpiperazin-1-yl]-4-oxoquinoline-3-carboxylic acid.

R-Grepafloxacin is a molecule that was designed as a part of a class of molecules called quinolone antibiotics. These molecules are designed to target and kill bacteria by inhibiting their ability to produce DNA. R-Grepafloxacin was specifically designed to target a type of bacteria called Gram-negative bacteria. Gram-negative bacteria are a type of bacteria that are resistant to many antibiotics. R-Grepafloxacin was designed to be more effective against Gram-negative bacteria than other quinolone antibiotics. R-Grepafloxacin was first approved for use in the United States in 1999..

3D structure

Cartesian coordinates

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

2D drawing

 

(R)-Grepafloxacin AIJTTZAVMXIJGM-SNVBAGLBSA-N chemical compound 2D structure molecule svg
(R)-Grepafloxacin

 

Molecule descriptors

 
IUPAC name1-cyclopropyl-6-fluoro-5-methyl-7-[(3R)-3-methylpiperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
InChI codeInChI=1S/C19H22FN3O3/c1-10-8-22(6-5-21-10)15-7-14-16(11(2)17(15)20)18(24)13(19(25)26)9-23(14)12-3-4-12/h7,9-10,12,21H,3-6,8H2,1-2H3,(H,25,26)/t10-/m1/s1
InChI KeyAIJTTZAVMXIJGM-SNVBAGLBSA-N
SMILESCc1c(F)c(N2CCN[C@H](C)C2)cc2c1c(=O)c(C(=O)O)cn2C1CC1

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.

  • (+)-Grepafloxacin
  • (R)-Grepafloxacin
  • (R)-grepafloxacin
  • 146761-68-4
  • 3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-((3R)-3-methyl-1-piperazinyl)-4-oxo-
  • 3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-, (R)-
  • B60Q83J4KP
  • BIDD:GT0300
  • D-Grepafloxacin
  • Grepafloxacin, (+)-
  • Grepafloxacin, (R)-
  • Q27274417

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC587541
  • UNII-B60Q83J4KP
  • SCHEMBL34157

Physico-Chemical properties

IUPAC name1-cyclopropyl-6-fluoro-5-methyl-7-[(3R)-3-methylpiperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
Molecular formulaC19H22FN3O3
Molecular weight359.395
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity105.02
LogP2.7
Topological polar surface area74.6

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.