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MedKoo Cat#: 461650 | Name: Flomoxef

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Flomoxef, also known as S 6315, is an oxacephem antibiotic. Flomoxef showed excellent in vitro activity against clinically important gram-positive and gram-negative pathogens causing community- and hospital-associated infections. he MICs of flomoxef at which 90% of clinical isolates were inhibited was >128 microg/mL in 26 isolates of Mycobacterium abscessus and 4 microg/mL in 31 isolates of M. fortuitum. Three out of 4 clinical M. peregrinum isolates were inhibited by flomoxef at concentrations of 4 microg/mL or less.

Chemical Structure

Flomoxef
Flomoxef
CAS#99665-00-6 (free acid)

Theoretical Analysis

MedKoo Cat#: 461650

Name: Flomoxef

CAS#: 99665-00-6 (free acid)

Chemical Formula: C15H18F2N6O7S2

Exact Mass: 496.0646

Molecular Weight: 496.46

Elemental Analysis: C, 36.29; H, 3.65; F, 7.65; N, 16.93; O, 22.56; S, 12.92

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
99665-00-6 (free acid) 92823-03-5 (sodium)
Synonym
Flomoxef; Flomoxefum; Flomoxefo; FMOX; 6315-S; 6315S; 6315 S;
IUPAC/Chemical Name
(6R,7R)-7-(2-((difluoromethyl)thio)acetamido)-3-(((1-(2-hydroxyethyl)-1H-tetrazol-5-yl)thio)methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
InChi Key
UHRBTBZOWWGKMK-DOMZBBRYSA-N
InChi Code
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
SMILES Code
O=C(C(N12)=C(CSC3=NN=NN3CCO)CO[C@]2([H])[C@](OC)(NC(CSC(F)F)=O)C1=O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 496.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Cui L, Li Y, Lv Y, Xue F, Liu J. Antimicrobial resistance surveillance of flomoxef in China. J Infect Chemother. 2015 May;21(5):402-4. doi: 10.1016/j.jiac.2015.01.008. Epub 2015 Jan 30. PubMed PMID: 25694055. 2: Lee CH, Su LH, Chen FJ, Tang YF, Li CC, Chien CC, Liu JW. 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 minimum inhibitory concentration of flomoxef: a retrospective study. Int J Antimicrob Agents. 2015 Dec;46(6):610-5. doi: 10.1016/j.ijantimicag.2015.07.020. Epub 2015 Sep 7. PubMed PMID: 26387064. 3: Yang Q, Zhang H, Cheng J, Xu Z, Hou X, Xu Y. Flomoxef showed excellent in vitro activity against clinically important gram-positive and gram-negative pathogens causing community- and hospital-associated infections. Diagn Microbiol Infect Dis. 2015 Apr;81(4):269-74. doi: 10.1016/j.diagmicrobio.2015.01.001. Epub 2015 Jan 9. PubMed PMID: 25641126. 4: Yang Q, Zhang H, Cheng J, Xu Z, Xu Y, Cao B, Kong H, Ni Y, Yu Y, Sun Z, Hu B, Huang W, Wang Y, Wu A, Feng X, Liao K, Shen D, Hu Z, Chu Y, Lu J, Su J, Gui B, Duan Q, Zhang S, Shao H. In vitro activity of flomoxef and comparators against Escherichia coli, Klebsiella pneumoniae and Proteus mirabilis producing extended-spectrum β-lactamases in China. Int J Antimicrob Agents. 2015 May;45(5):485-90. doi: 10.1016/j.ijantimicag.2014.11.012. Epub 2014 Dec 31. PubMed PMID: 25600890. 5: Matsumura Y, Yamamoto M, Nagao M, Komori T, Fujita N, Hayashi A, Shimizu T, Watanabe H, Doi S, Tanaka M, Takakura S, Ichiyama S. Multicenter retrospective study of cefmetazole and flomoxef for treatment of extended-spectrum-β-lactamase-producing Escherichia coli bacteremia. Antimicrob Agents Chemother. 2015 Sep;59(9):5107-13. doi: 10.1128/AAC.00701-15. Epub 2015 Jun 22. PubMed PMID: 26100708; PubMed Central PMCID: PMC4538479. 6: Matsumura Y, Yamamoto M, Nagao M, Tanaka M, Takakura S, Ichiyama S. In vitro activities and detection performances of cefmetazole and flomoxef for extended-spectrum β-lactamase and plasmid-mediated AmpC β-lactamase-producing Enterobacteriaceae. Diagn Microbiol Infect Dis. 2016 Apr;84(4):322-7. doi: 10.1016/j.diagmicrobio.2015.12.001. Epub 2015 Dec 11. PubMed PMID: 26782634. 7: Kravtsova OY, Paramonov SA, Vasilevich NI, Kazyulkin DN, Vlasova E, Engsig M. Determination of flomoxef in human plasma by liquid chromatography/electrospray ionization tandem mass spectrometry. Biomed Chromatogr. 2013 Dec;27(12):1609-14. doi: 10.1002/bmc.2968. Epub 2013 Jun 18. PubMed PMID: 23780743. 8: Yang CC, Li SH, Chuang FR, Chen CH, Lee CH, Chen JB, Wu CH, Lee CT. Discrepancy between effects of carbapenems and flomoxef in treating nosocomial hemodialysis access-related bacteremia secondary to extended spectrum beta-lactamase producing Klebsiella pneumoniae in patients on maintenance hemodialysis. BMC Infect Dis. 2012 Sep 5;12:206. doi: 10.1186/1471-2334-12-206. PubMed PMID: 22947300; PubMed Central PMCID: PMC3507710. 9: Ito A, Tatsumi YM, Wajima T, Nakamura R, Tsuji M. Evaluation of antibacterial activities of flomoxef against ESBL producing Enterobacteriaceae analyzed by Monte Carlo simulation. Jpn J Antibiot. 2013 Apr;66(2):71-86. PubMed PMID: 23951726. 10: Simon C, Simon M. In vitro activity of flomoxef and cefazolin in combination with vancomycin. Infection. 1991;19 Suppl 5:S276-8. PubMed PMID: 1783443. 11: Masuda Z, Kurosaki Y, Ishino K, Yamauchi K, Sano S. Pharmacokinetic analysis of flomoxef in children undergoing cardiopulmonary bypass and modified ultrafiltration. Gen Thorac Cardiovasc Surg. 2008 Apr;56(4):163-9. doi: 10.1007/s11748-007-0208-5. Epub 2008 Apr 10. PubMed PMID: 18401677. 12: Mochizuki K, Torisaki M, Yamashita Y, Komatsu M, Tanahashi T. Intravitreal flomoxef sodium in rabbits. Ophthalmic Res. 1993;25(2):128-36. PubMed PMID: 8321517. 13: Werner H, Heizmann W, Luft G. In vitro activity of flomoxef compared to moxalactam, cefoxitin, cefotaxime, and clindamycin against anaerobes. Arzneimittelforschung. 1988 Nov;38(11):1553-6. PubMed PMID: 3214438. 14: Hishikawa S, Kobayashi E, Sugimoto K, Miyata M, Fujimura A. Diurnal variation in the biliary excretion of flomoxef in patients with percutaneous transhepatic biliary drainage. Br J Clin Pharmacol. 2001 Jul;52(1):65-8. PubMed PMID: 11453891; PubMed Central PMCID: PMC2014506. 15: Simon C, Simon M, Plieth C. In vitro activity of flomoxef in comparison to other cephalosporins. Infection. 1988 Mar-Apr;16(2):131-4. PubMed PMID: 3372024. 16: Lee CH, Su LH, Tang YF, Liu JW. Treatment of ESBL-producing Klebsiella pneumoniae bacteraemia with carbapenems or flomoxef: a retrospective study and laboratory analysis of the isolates. J Antimicrob Chemother. 2006 Nov;58(5):1074-7. Epub 2006 Sep 13. PubMed PMID: 16971415. 17: Shimada M, Takenaka K, Sugimachi K. A comprehensive multi-institutional study of empiric therapy with flomoxef in surgical infections of the digestive organs. The Kyushu Research Group for Surgical Infection. J Chemother. 1994 Aug;6(4):251-6. PubMed PMID: 7830103. 18: Hishikawa S, Sugimoto K, Kobayashi E, Kumagai Y, Fujimura A. Dosing-time-dependent variation in biliary excretion of flomoxef in rats. Chronobiol Int. 2003 May;20(3):463-71. PubMed PMID: 12868541. 19: Lee CH, Chu C, Liu JW, Chen YS, Chiu CJ, Su LH. Collateral damage of flomoxef therapy: in vivo development of porin deficiency and acquisition of blaDHA-1 leading to ertapenem resistance in a clinical isolate of Klebsiella pneumoniae producing CTX-M-3 and SHV-5 beta-lactamases. J Antimicrob Chemother. 2007 Aug;60(2):410-3. Epub 2007 Jun 18. PubMed PMID: 17576696. 20: Chen YC, Hung CC, Lin SF, Chang SC, Hsieh WC. Comparison of flomoxef with latamoxef in the treatment of sepsis and/or Gram-negative bacteremia in adult patients. Int J Antimicrob Agents. 1996 May;7(1):69-74. PubMed PMID: 18611739.