Gemifloxacin Mesylate - CAS 210353-53-0
Catalog number:
210353-53-0
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C19H24FN5O7S
Molecular Weight:
485.50
COA:
Inquire
Targets:
Antibacterial
Description:
Gemifloxacin Mesylate,a fluoroquinolone, is an oral broad-spectrum antibacterial agent that show great in vitro activity against a wide variety of respiratory tract pathogens and is used to treat mild-to-moderate pneumonia.
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Purity:
> 95%
Appearance:
Beige Solid
Synonyms:
7-[(4E)-3-(aminomethyl)-4-methoxyiminopyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylic acid;methanesulfonic acid 7-(3-aminomethyl-4-methoxyimino-pyrrolidine-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-(1,8)-naphthyridine-3-c
Solubility:
Soluble to 30mg/mL in DMSO
Storage:
Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -64℃ for long term (months to years).
MSDS:
Inquire
Shelf Life:
2 years
Quantity:
Milligrams-Grams
Melting Point:
235-237°C
InChIKey:
JIYMVSQRGZEYAX-YDHFHHHVSA-N
InChI:
1S/C18H20FN5O4.CH4O3S/c1-28-22-14-8-23(6-9(14)5-20)17-13(19)4-11-15(25)12(18(26)27)7-24(10-2-3-10)16(11)21-17;1-5(2,3)4/h4,7,9-10H,2-3,5-6,8,20H2,1H3,(H,26,27);1H3,(H,2,3,4)/b22-14-;
Canonical SMILES:
CON=C1CN(CC1CN)C2=C(C=C3C(=O)C(=CN(C3=N2)C4CC4)C(=O)O)F.CS(=O)(=O)O
1.In vitro activity of WQ-3810, a novel fluoroquinolone, against multidrug-resistant and fluoroquinolone-resistant pathogens.
Kazamori D1, Aoi H2, Sugimoto K2, Ueshima T2, Amano H2, Itoh K2, Kuramoto Y2, Yazaki A2. Int J Antimicrob Agents. 2014 Nov;44(5):443-9. doi: 10.1016/j.ijantimicag.2014.07.017. Epub 2014 Sep 1.
The aim of this study was to examine the in vitro antibacterial activity of WQ-3810, a new fluoroquinolone, against clinically relevant pathogens such as Acinetobacter baumannii, Escherichia coli and Streptococcus pneumoniae, including multidrug-resistant (MDR) and fluoroquinolone-resistant (FQR) isolates, compared with those of ciprofloxacin, levofloxacin, moxifloxacin and gemifloxacin. WQ-3810 demonstrated the most potent activity against the antimicrobial-resistant pathogens tested. Against A. baumannii, including MDR isolates, the potency of WQ-3810 [minimum inhibitory concentration for 90% of the organisms (MIC(90))=1 mg/L] was more than eight-fold higher than that of ciprofloxacin (64 mg/L) and levofloxacin (8 mg/L). Against E. coli and S. pneumoniae, including FQR isolates, WQ-3810 (MIC(90)=4 mg/L and 0.06 mg/L, respectively) was also more active than ciprofloxacin (64 mg/L and 2 mg/L) and levofloxacin (32 mg/L and 2 mg/L). Furthermore, WQ-3810 was the most potent among the fluoroquinolones tested against meticillin-resistant Staphylococcus aureus (MRSA) and Neisseria gonorrhoeae, including FQR isolates.
2.Structural elucidation of gemifloxacin mesylate degradation product.
Paim CS1,2, Führ F1, Martins MT1, Gnoatto S1, Bajerski L2, Garcia CV1, Steppe M1, Schapoval EE1. Biomed Chromatogr. 2016 Mar;30(3):459-65. doi: 10.1002/bmc.3569. Epub 2015 Sep 2.
Gemifloxacin mesylate (GFM), chemically (R,S)-7-[(4Z)-3-(aminomethyl)-4-(methoxyimino)-1-pyrrolidinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid methanesulfonate, is a synthetic broad-spectrum antibacterial agent. Although many papers have been published in the literature describing the stability of fluorquinolones, little is known about the degradation products of GFM. Forced degradation studies of GFM were performed using radiation (UV-A), acid (1 mol L(-1) HCl) and alkaline conditions (0.2 mol L(-1) NaOH). The main degradation product, formed under alkaline conditions, was isolated using semi-preparative LC and structurally elucidated by nuclear magnetic resonance (proton - (1) H; carbon - (13) C; correlate spectroscopy - COSY; heteronuclear single quantum coherence - HSQC; heteronuclear multiple-bond correlation - HMBC; spectroscopy - infrared, atomic emission and mass spectrometry techniques). The degradation product isolated was characterized as sodium 7-amino-1-pyrrolidinyl-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate, which was formed by loss of the 3-(aminomethyl)-4-(methoxyimino)-1-pyrrolidinyl ring and formation of the sodium carboxylate.
3.Photochemical properties of gemifloxacin: a laser flash photolysis study.
Xu Y1, Liu Y2, Zhao J1, Li H2, Zhang P2, Wang W3. J Photochem Photobiol B. 2015 Feb;143:30-7. doi: 10.1016/j.jphotobiol.2014.12.014. Epub 2014 Dec 19.
The photochemical properties of gemifloxacin (GEFX), a fluoroquinolone antibacterial drug that exhibits phototoxicity toward biological substrates, were studied in aqueous solutions by laser flash photolysis (LFP) and pulse radiolysis. GEFX triplet state ((3)GEFX(∗)) absorption spectra showed maximum absorption at 510nm. (3)GEFX(∗) was quenched by naproxen (NAP) via energy transfer with a rate constant of 1.2×10(8)dm(3)mol(-1)s(-1). The energy of (3)GEFX(∗) was 266kJmol(-1) and the transient absorption spectra showed direct evidence of electron transfer from 2'-deoxyguanosine-5'-monophosphate, N,N,N',N'-tetramethyl-p-phenylenediamine, and tryptophan to (3)GEFX(∗) with bimolecular reaction rate constants of 4.1×10(6), 2.0×10(7), and 2.2×10(7)dm(3)mol(-1)s(-1), respectively. The rate constants for reactions of GEFX with OH, eaq(-) were found to be 1.5×10(10) and 1.4×10(10)dm(3)mol(-1)s(-1), respectively. The mechanisms and products of the photosensitive damage of lysozyme were related to the GEFX concentration, irradiation time, and ambient conditions.
4.Killing of Streptococcus pneumoniae by azithromycin, clarithromycin, erythromycin, telithromycin and gemifloxacin using drug minimum inhibitory concentrations and mutant prevention concentrations.
Blondeau JM1, Shebelski SD2, Hesje CK3. Int J Antimicrob Agents. 2015 Jun;45(6):594-9. doi: 10.1016/j.ijantimicag.2014.12.034. Epub 2015 Feb 16.
Streptococcus pneumoniae continues to be a significant respiratory pathogen, and increasing antimicrobial resistance compromises the use of β-lactam and macrolide antibiotics. Bacterial eradication impacts clinical outcome, and bacterial loads at the site of infection may fluctuate. Killing of two macrolide- and quinolone-susceptible clinical S. pneumoniae isolates by azithromycin, clarithromycin, erythromycin, telithromycin and gemifloxacin against varying bacterial densities was determined using the measured minimum inhibitory concentration (MIC) and mutant prevention concentration (MPC). For kill experiments, 10(6)-10(9) CFU/mL were exposed to the drug and were sampled at 0, 0.5, 1, 2, 3, 4, 6, 12 and 24 h following drug exposure. The log(10) reduction and percent reduction (kill) of viable cells was recorded. MICs and MPCs (mg/L) for azithromycin, clarithromycin, erythromycin, telithromycin and gemifloxacin were 0.063-0.125/0.5-1, 0.
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CAS 210353-53-0 Gemifloxacin Mesylate

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