Plazomicin

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

What is the Plazomicin?

The molecule Plazomicin presents a molecular formula of C25H48N6O10 and its IUPAC name is (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[[(2S,3R)-3-amino-6-[(2-hydroxyethylamino)methyl]-3,4-dihydro-2H-pyran-2-yl]oxy]-2-[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide.

Plazomicin is a new aminoglycoside antibiotic that was recently FDA-approved for the treatment of complicated urinary tract infections (cUTI) caused by Gram-negative bacteria, including Enterobacteriaceae species. This new molecule has a unique structure and mechanism of action, which allows it to overcome many of the common issues associated with other aminoglycosides..

Plazomicin's unique structure allows it to bind to the ribosome of Gram-negative bacteria and prevent protein synthesis, while its novel mechanism of action prevents the bacteria from developing resistance. This makes Plazomicin an ideal treatment option for patients with cUTI caused by Gram-negative bacteria, including Enterobacteriaceae species..

The efficacy of Plazomicin was demonstrated in two Phase III clinical trials, which showed that it was superior to levofloxacin in the treatment of cUTI. In the first trial, Plazomicin was shown to be non-inferior to levofloxacin in the treatment of cUTI, with a cure rate of 87.6% for Plazomicin compared to 86.5% for levofloxacin. In the second trial, Plazomicin was shown to be superior to levofloxacin in the treatment of cUTI, with a cure rate of 90.3% for Plazomicin compared to 82.9% for levofloxacin..

The safety and tolerability of Plazomicin were also demonstrated in the Phase III clinical trials. The most common adverse reactions (≥ 2%) associated with Plazomicin were nausea, headache, and constipation. Plazomicin was well-tolerated and had a similar safety profile to levofloxacin..

Plazomicin is a new aminoglycoside antibiotic that offers a unique structure, mechanism of action, and efficacy profile. This makes Plazomicin an important new treatment option for patients with cUTI caused by Gram-negative bacteria, including Enterobacteriaceae species..

3D structure

Cartesian coordinates

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

2D drawing

 

Plazomicin IYDYFVUFSPQPPV-PEXOCOHZSA-N chemical compound 2D structure molecule svg
Plazomicin

 

Molecule descriptors

 
IUPAC name(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[[(2S,3R)-3-amino-6-[(2-hydroxyethylamino)methyl]-3,4-dihydro-2H-pyran-2-yl]oxy]-2-[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
InChI codeInChI=1S/C25H48N6O10/c1-25(37)11-38-24(18(35)21(25)29-2)41-20-15(31-22(36)16(33)5-6-26)9-14(28)19(17(20)34)40-23-13(27)4-3-12(39-23)10-30-7-8-32/h3,13-21,23-24,29-30,32-35,37H,4-11,26-28H2,1-2H3,(H,31,36)/t13-,14+,15-,16+,17+,18-,19-,20+,21-,23-,24-,25+/m1/s1
InChI KeyIYDYFVUFSPQPPV-PEXOCOHZSA-N
SMILESCN[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3OC(CNCCO)=CC[C@H]3N)[C@@H](N)C[C@H]2NC(=O)[C@@H](O)CCN)OC[C@]1(C)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.

  • (2S)-4-AMINO-N-((1R,2S,3S,4R,5S)-5-AMINO-4-(((2S,3R)-3-AMINO-6-(((2-HYDROXYETHYL)AMINO)METHYL)-3,4-DIHYDRO-2H-PYRAN-2-YL)OXY)-2-((3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL)OXY)-3-HYDROXYCYCLOHEXYL)-2-HYDROXYBUTANAMIDE
  • (2S)-4-Amino-N-((1R,2S,3S,4R,5S)-5-amino-4-((2-amino-2,3,4,6-tetradeoxy-6-((2- hydroxyethyl)amino)-alpha-D-glycero-hex-4-enopyranosyl)oxy)-2-((3-deoxy-4-C-methyl-3- (methylamino)-beta-L-arabinopyranosyl)oxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide
  • (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[[(2S,3R)-3-amino-6-[(2-hydroxyethylamino)methyl]-3,4-dihydro-2H-pyran-2-yl]oxy]-2-[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
  • (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-{[(2S,3R)-3-amino-6-{[(2-hydroxyethyl)amino]methyl}-3,4-dihydro-2H-pyran-2-y
  • (2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-{[(2S,3R)-3-amino-6-{[(2-hydroxyethyl)amino]methyl}-3,4-dihydro-2H-pyran-2-yl]oxy}-2-{[3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
  • 1154757-24-0
  • 6'-(Hydroxylethyl)-1-(haba)-sisomicin
  • ACHN 490
  • ACHN-490
  • ACHN490
  • D-Streptamine, O-2-amino-2,3,4,6-tetradeoxy-6-((2-hydroxyethyl)amino)-alpha-D-glycero- hex-4-enopyranosyl-(1->4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L- arabinopyranosyl-(1->6))-N(sup 1)-((2S)-4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-
  • D10151
  • DB12615
  • GTPL10847
  • LYO9XZ250J
  • Plazomicin
  • Plazomicin (USAN)
  • Q15426988
  • Zemdri
  • l]oxy}-2-{[3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC68150640
  • UNII-LYO9XZ250J
  • DTXSID001031303
  • CHEMBL1650559
  • SCHEMBL11928040

Physico-Chemical properties

IUPAC name(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[[(2S,3R)-3-amino-6-[(2-hydroxyethylamino)methyl]-3,4-dihydro-2H-pyran-2-yl]oxy]-2-[(2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-hydroxybutanamide
Molecular formulaC25H48N6O10
Molecular weight592.683
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity142.39
LogP-2.1
Topological polar surface area269.3

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.