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MedKoo Cat#: 330148 | Name: Flomoxef sodium
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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 sodium
Flomoxef sodium
CAS#92823-03-5 (sodium)

Theoretical Analysis

MedKoo Cat#: 330148

Name: Flomoxef sodium

CAS#: 92823-03-5 (sodium)

Chemical Formula: C15H17F2N6NaO7S2

Exact Mass: 0.0000

Molecular Weight: 518.44

Elemental Analysis: C, 34.75; H, 3.31; F, 7.33; N, 16.21; Na, 4.43; O, 21.60; S, 12.37

Price and Availability

Size Price Availability Quantity
10mg USD 350.00 2 Weeks
25mg USD 650.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
99665-00-6 (free acid) 92823-03-5 (sodium)
Synonym
Flomoxef sodium; FMOX sodium; Flumarin; 6315-S sodium; 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-carboxylate
InChi Key
PPPZBOLFWGINKN-YLCXCWDSSA-M
InChi Code
InChI=1S/C15H18F2N6O7S2.Na/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);/q;+1/p-1/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-].[Na+]
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 518.44 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: Lee CH, Chen IL, Li CC, Chien CC. Clinical benefit of ertapenem compared to flomoxef for the treatment of cefotaxime-resistant Enterobacteriaceae bacteremia. Infect Drug Resist. 2018 Feb 23;11:257-266. doi: 10.2147/IDR.S146923. eCollection 2018. PubMed PMID: 29503575; PubMed Central PMCID: PMC5826091. 2: Yu X, Wang F, Li J, Shan W, Zhu B, Wang J. Separation and characterization of unknown impurities and isomers in flomoxef sodium by LC-IT-TOF MS and study of their negative-ion fragmentation regularities. J Pharm Biomed Anal. 2017 Jun 5;140:81-90. doi: 10.1016/j.jpba.2017.03.032. Epub 2017 Mar 19. PubMed PMID: 28343077. 3: 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. 4: 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. 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: 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. 7: 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. 8: 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. 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: 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. 11: 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. 12: Lee CH, Liu JW, Li CC, Chien CC, Tang YF, Su LH. Spread of ISCR1 elements containing blaDHA-₁ and multiple antimicrobial resistance genes leading to increase of flomoxef resistance in extended-spectrum-beta-lactamase-producing Klebsiella pneumoniae. Antimicrob Agents Chemother. 2011 Sep;55(9):4058-63. doi: 10.1128/AAC.00259-11. Epub 2011 Jul 11. PubMed PMID: 21746945; PubMed Central PMCID: PMC3165323. 13: Inoshita A, Yokoi H, Matsumoto F, Yao T, Kawano K, Furukawa M, Ikeda K. A randomized prospective study of oral levofloxacin vs intravenous flomoxef prophylaxis in postoperative infection after endoscopic sinus surgery. Am J Otolaryngol. 2010 Sep-Oct;31(5):360-3. doi: 10.1016/j.amjoto.2009.06.001. Epub 2009 Jul 29. PubMed PMID: 20015788. 14: Tsai MS, Tang YF, Eng HL. In vitro activity of flomoxef against rapidly growing mycobacteria. J Chemother. 2008 Jun;20(3):303-6. PubMed PMID: 18606583. 15: 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. 16: 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. 17: Miyamoto M, Watanabe Y, Mizuki N. [Preoperatively administered flomoxef sodium concentration in aqueous humor]. Nippon Ganka Gakkai Zasshi. 2007 Apr;111(4):326-30. Japanese. PubMed PMID: 17461038. 18: Togo S, Tanaka K, Matsuo K, Nagano Y, Ueda M, Morioka D, Endo I, Shimada H. Duration of antimicrobial prophylaxis in patients undergoing hepatectomy: a prospective randomized controlled trial using flomoxef. J Antimicrob Chemother. 2007 May;59(5):964-70. Epub 2007 Feb 28. PubMed PMID: 17329271. 19: 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. 20: Mizuki N, Watanabe Y, Miyamoto M, Iijima Y, Takiyama N, Ito Y, Ito N, Nishida T, Iwata S, Endo Y, Ito D. Flomoxef sodium and levofloxacin concentrations in aqueous humor. Ocul Immunol Inflamm. 2005 Apr-Jun;13(2-3):229-34. PubMed PMID: 16019684.