Ozenoxacin

  • CAT Number: I008531
  • CAS Number: 245765-41-7
  • Molecular Formula: C21H21N3O3
  • Molecular Weight: 363.417
  • Purity: ≥95%
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Ozenoxacin(CAT: I008531) is a topical antibiotic that belongs to the quinolone class of antimicrobial agents. It is primarily used for the treatment of impetigo, a highly contagious bacterial skin infection. Ozenoxacin works by inhibiting the activity of bacterial enzymes that are essential for DNA replication and cell division, ultimately leading to bacterial cell death. Clinical studies have shown that ozenoxacin is effective in treating impetigo, and it is generally well-tolerated with few side effects. However, as with all antibiotics, there is a risk of developing bacterial resistance with prolonged or inappropriate use of the drug. 

Catalog Number I008531
CAS Number 245765-41-7
Synonyms

GF-001001-00; M-5120; T-3912; GF-00100100; Ozenoxacin;1-cyclopropyl-8-methyl-7-(5-methyl-6-(methylamino)pyridin-3-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Molecular Formula

C21H21N3O3

Purity 95%
Target O=C(C1=CN(C2CC2)C3=C(C=CC(C4=CC(C)=C(NC)N=C4)=C3C)C1=O)O
Solubility Soluble in DMSO
Storage 0 - 4 °C for short term, or -20 °C for long term
IUPAC Name 1-cyclopropyl-8-methyl-7-[5-methyl-6-(methylamino)pyridin-3-yl]-4-oxoquinoline-3-carboxylic acid
InChI InChI=1S/C21H21N3O3/c1-11-8-13(9-23-20(11)22-3)15-6-7-16-18(12(15)2)24(14-4-5-14)10-17(19(16)25)21(26)27/h6-10,14H,4-5H2,1-3H3,(H,22,23)(H,26,27)
InChIKey XPIJWUTXQAGSLK-UHFFFAOYSA-N
SMILES CC1=C(N=CC(=C1)C2=C(C3=C(C=C2)C(=O)C(=CN3C4CC4)C(=O)O)C)NC
Reference

1. J Infect Chemother. 2017 Jun;23(6):374-380. doi: 10.1016/j.jiac.2017.03.004. Epub
2017 Apr 4.
<br>
Bactericidal activity and post-antibiotic effect of ozenoxacin against
Propionibacterium acnes.
<br>
Kanayama S(1), Okamoto K(2), Ikeda F(3), Ishii R(3), Matsumoto T(4), Hayashi
N(5), Gotoh N(5).
<br>
Author information: <br>
(1)Drug Development Research Laboratories, Kyoto R&D Center, Maruho Co., Ltd.,
Japan; Department of Microbiology and Infection Control Science, Kyoto
Pharmaceutical University, Japan. Electronic address:
[email protected].
(2)Drug Development Research Laboratories, Kyoto R&D Center, Maruho Co., Ltd.,
Japan; Department of Microbiology and Infection Control Science, Kyoto
Pharmaceutical University, Japan.
(3)Strategic Research Planning & Management Dept., Kyoto R&D Center, Maruho Co.,
Ltd., Japan.
(4)Drug Development Research Laboratories, Kyoto R&D Center, Maruho Co., Ltd.,
Japan.
(5)Department of Microbiology and Infection Control Science, Kyoto Pharmaceutical
University, Japan.
<br>
Ozenoxacin, a novel non-fluorinated topical quinolone, is used for the treatment
of acne vulgaris in Japan. We investigated bactericidal activity and
post-antibiotic effect (PAE) of ozenoxacin against Propionibacterium acnes, a
major causative bacterium of acne vulgaris. The minimum inhibitory concentrations
(MICs) of ozenoxacin against 3 levofloxacin-susceptible strains (MIC of
levofloxacin; ≤4 μg/mL) and 3 levofloxacin-resistant strains (MIC of
levofloxacin; ≥8 μg/mL) ranged from 0.03 to 0.06 μg/mL and from 0.25 to
0.5 μg/mL, respectively. These MICs of ozenoxacin were almost the same or lower
than nadifloxacin and clindamycin. The minimum bactericidal concentrations (MBCs)
of ozenoxacin against the levofloxacin-susceptible and -resistant strains were
from 0.06 to 8 μg/mL and from 0.5 to 4 μg/mL, respectively. These MBCs were lower
than those of nadifloxacin and clindamycin. In time-kill assay, ozenoxacin at
1/4, 1 and 4 times the respective MIC against both levofloxacin-susceptible and
-resistant strains showed a concentration-dependent bactericidal activity.
Ozenoxacin at 4 times the MICs against the levofloxacin-susceptible strains
showed more potent and more rapid onset of bactericidal activity compared to
nadifloxacin and clindamycin at 4 times the respective MICs. The PAEs of
ozenoxacin at 4 times the MICs against the levofloxacin-susceptible strains were
from 3.3 to 17.1 h, which were almost the same or longer than nadifloxacin and
clindamycin. In contrast, the PAEs were hardly induced by any antimicrobial
agents against the levofloxacin-resistant strains. The present findings suggest
that ozenoxacin has a potent bactericidal activity against both
levofloxacin-susceptible and -resistant P. acnes, and a long-lasting PAE against
levofloxacin-susceptible P. acnes.

<br>

2. Future Microbiol. 2014;9(8 Suppl):S1-2. doi: 10.2217/fmb.14.80.
<br>
Ozenoxacin: a review of absorption, dermal exposure and toxicity, tolerability
and safety studies.
<br>
Gropper S.

<br>
3. Antimicrob Agents Chemother. 2013 Dec;57(12):6389-92. doi: 10.1128/AAC.01509-13.
Epub 2013 Sep 30.
<br>
In vitro activity of Ozenoxacin against quinolone-susceptible and
quinolone-resistant gram-positive bacteria.
<br>
López Y(1), Tato M, Espinal P, Garcia-Alonso F, Gargallo-Viola D, Cantón R, Vila
J.
<br>
Author information: <br>
(1)Barcelona Centre for International Health Research (CRESIB), Barcelona, Spain.
<br>
In vitro activity of ozenoxacin, a novel nonfluorinated topical (L. D. Saravolatz
and J. Leggett, Clin. Infect. Dis. 37:1210-1215, 2003) quinolone, was compared
with the activities of other quinolones against well-characterized
quinolone-susceptible and quinolone-resistant Gram-positive bacteria. Ozenoxacin
was 3-fold to 321-fold more active than other quinolones. Ozenoxacin could
represent a first-in-class nonfluorinated quinolone for the topical treatment of
a broad range of dermatological infections.
<br>

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