Flomoxef
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| Category | Antibiotics |
| Catalog number | BBF-01715 |
| CAS | 99665-00-6 |
| Molecular Weight | 496.47 |
| Molecular Formula | C15H18F2N6O7S2 |
| Purity | >98% |
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Description
Flomoxef is a semi-synthetic oxygen cephalene antibiotic. It has anti-gram-positive bacteria and gram-negative bacteria activity. However, it has weak antibacterial activity against Cloacae, Citrobacter and Serratia marcescens, and has no effect on Pseudomonas aeruginosa, and has better effect on anaerobes than other cephalosporins.
Specification
| Related CAS | 92823-03-5 (sodium salt) |
| Synonyms | Flomoxefum; FMOX; Flumarin; Furumarin |
| Storage | Store at -20°C |
| IUPAC Name | (6R,7R)-7-[[2-(difluoromethylsulfanyl)acetyl]amino]-3-[[1-(2-hydroxyethyl)tetrazol-5-yl]sulfanylmethyl]-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Canonical SMILES | COC1(C2N(C1=O)C(=C(CO2)CSC3=NN=NN3CCO)C(=O)O)NC(=O)CSC(F)F |
| InChI | InChI=1S/C15H18F2N6O7S2/c1-29-15(18-8(25)6-31-13(16)17)11(28)23-9(10(26)27)7(4-30-12(15)23)5-32-14-19-20-21-22(14)2-3-24/h12-13,24H,2-6H2,1H3,(H,18,25)(H,26,27)/t12-,15+/m1/s1 |
| InChI Key | UHRBTBZOWWGKMK-DOMZBBRYSA-N |
Properties
| Appearance | Oily Matter |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 232-233°C |
| Melting Point | 82.5-87.5°C |
| Density | 1.85±0.1 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1.Comparative effectiveness of flomoxef versus carbapenems in the treatment of bacteraemia due to extended-spectrum β-lactamase-producing Escherichia coli or Klebsiella pneumoniae with emphasis on min
Lee CH1, Su LH2, Chen FJ3, Tang YF4, Li CC4, Chien CC4, Liu JW5. Int J Antimicrob Agents. 2015 Dec;46(6):610-5. doi: 10.1016/j.ijantimicag.2015.07.020. Epub 2015 Sep 7.
This study compared treatment outcomes of adult patients with bacteraemia due to extended-spectrum β-lactamase-producing Escherichia coli or Klebsiella pneumoniae (ESBL-EK) receiving flomoxef versus those receiving a carbapenem as definitive therapy. In propensity score matching (PSM) analysis, case patients receiving flomoxef shown to be active in vitro against ESBL-EK were matched with controls who received a carbapenem. The primary endpoint was 30-day crude mortality. The flomoxef group had statistically significantly higher sepsis-related mortality (27.3% vs. 10.5%) and 30-day mortality (28.8% vs. 12.8%) than the carbapenem group. Of the bacteraemic episodes caused by isolates with a MICflomoxef of ≤1 mg/L, sepsis-related mortality rates were similar between the two treatment groups (8.7% vs. 6.4%; P=0.73). The sepsis-related mortality rate of the flomoxef group increased to 29.6% and 50.0% of episodes caused by isolates with a MICflomoxef of 2-4 mg/L and 8 mg/L, respectively, which was significantly higher than the carbapenem group (12.
2.In vitro activities and detection performances of cefmetazole and flomoxef for extended-spectrum β-lactamase and plasmid-mediated AmpC β-lactamase-producing Enterobacteriaceae.
Matsumura Y1, Yamamoto M2, Nagao M3, Tanaka M4, Takakura S5, Ichiyama S6. Diagn Microbiol Infect Dis. 2016 Apr;84(4):322-7. doi: 10.1016/j.diagmicrobio.2015.12.001. Epub 2015 Dec 11.
To investigate the in vitro activities of cephamycins (cefmetazole and flomoxef) for extended-spectrum β-lactamase (ESBL)- and plasmid-mediated AmpC β-lactamase (pAmpC)-producing Enterobacteriaceae, a total of 574 third-generation cephalosporin-resistant clinical isolates were collected at a Japanese multicenter study. PCR and sequencing identified 394 isolates with only ESBL genes, 63 isolates with only pAmpC genes, and 6 isolates with both ESBL and pAmpC genes. blaCTX-M types predominated 95.5% of the ESBL genes, and blaCMY-2 predominated 91.3% of the pAmpC genes. The MIC50/90 values of cefmetazole and flomoxef were ≤1/4 and ≤1/≤1μg/mL for isolates with only ESBL genes, respectively, and 16/>16 and 8/16μg/mL for isolates with only pAmpC genes, respectively. Flomoxef ≥4μg/mL had the best screening performance for the detection of isolates with pAmpC genes. Flomoxef had better in vitro activities against ESBL-producing Enterobacteriaceae and provided a clearer distinction between ESBL and pAmpC-producing Enterobacteriaceae compared to cefmetazole.
3.Mechanism of resistance and antibacterial susceptibility in extended-spectrum β-lactamase phenotype Klebsiella pneumoniae and Klebsiella oxytoca isolated between 2000 and 2010 in Japan.
Sato T1, Hara T2, Horiyama T2, Kanazawa S2, Yamaguchi T2, Maki H2. J Med Microbiol. 2015 May;64(Pt 5):538-43. doi: 10.1099/jmm.0.000057. Epub 2015 Mar 26.
Clinical isolates of Klebsiella pneumoniae and Klebsiella oxytoca collected from 20 Japanese medical facilities between 2000 and 2010 were analysed to evaluate the mechanisms of resistance and antibacterial susceptibilities to 14 antimicrobials. Overall, eight of 484 (1.6%) K. pneumoniae and 19 of 359 (5.3%) K. oxytoca were determined to be extended-spectrum β-lactamase (ESBL) phenotype isolates, and the identified ESBLs amongst the K. pneumoniae isolates were CTX-M-2, -3, -14 and -15, and SHV-12. In contrast, overproduction of chromosomal β-lactamase OXY-2, which was due to a distinct mutation at the - 10 promoter region of this gene, conferred the ESBL phenotype to all the K. oxytoca isolates except one. Based on the Clinical and Laboratory Standards Institute breakpoints, all the ESBL phenotype K. pneumoniae were susceptible to doripenem, flomoxef, moxalactam (latamoxef), cefmetazole and tazobactam/piperacillin, whereas the ESBL phenotype K.
4.Flomoxef showed excellent in vitro activity against clinically important gram-positive and gram-negative pathogens causing community- and hospital-associated infections.
Yang Q1, Zhang H1, Cheng J1, Xu Z1, Hou X1, Xu Y2. Diagn Microbiol Infect Dis. 2015 Apr;81(4):269-74. doi: 10.1016/j.diagmicrobio.2015.01.001. Epub 2015 Jan 9.
The objective of this study was to better understand the in vitro activity of flomoxef against clinical pathogens. A total of 545 clinical isolates, including Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, methicillin-susceptible Staphylococcus aureus (MSSA), methicillin-resistant S. aureus, Streptococcus pneumoniae, and Streptococcus pyogenes, were isolated consecutively from clinical specimens from Peking Union Medical College Hospital in 2013. MICs were determined using broth microdilution method. esbl and ampC genes were detected by polymerase chain reaction and sequencing. Flomoxef showed excellent activity against E. coli, K. pneumoniae, and P. mirabilis isolates, with susceptibility rate of 88.8%, 88.3%, and 97.7%, separately. Moreover, flomoxef exhibited great activity against extended-spectrum beta-lactamase (ESBL) producers, with MIC50/MIC90 of 0.125/(0.5-1) μg/mL. Flomoxef showed MIC50/MIC90 of 0.5/0.5 μg/mL against MSSA, 0.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
