Fosfomycin
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| Category | Antibiotics |
| Catalog number | BBF-01848 |
| CAS | 23155-02-4 |
| Molecular Weight | 138.06 |
| Molecular Formula | C3H7O4P |
| Purity | 98% |
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Description
Fosfomycin is produced by the strain of Streptomyces fradiae and Str. viridochromogenes. It competitively inhibits enol pyruvate transferase and blocks the early stages of bacterial cell wall synthesis. And it has anti-gram positive bacteria and negative bacteria activity.
Specification
| Synonyms | Veramina; phosphomycin; Fosfomycinum; L-cis-1,2-epoxypropylphosphonic acid; (-)-(1R,2S)-(1,2-Epoxypropyl)phosphonic acid; (1R,2S)-epoxypropylphosphonate; cis-(1R,2S)-epoxypropylphosphonic acid; 1R-cis-(1,2-epoxypropyl)phosphonic acid |
| Storage | -20 °C |
| IUPAC Name | [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid |
| Canonical SMILES | CC1C(O1)P(=O)(O)O |
| InChI | InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1 |
| InChI Key | YMDXZJFXQJVXBF-STHAYSLISA-N |
Properties
| Appearance | Crystalline |
| Application | Anti-Bacterial Agents |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 342.7±52.0 °C at 760 mmHg |
| Melting Point | 94°C |
| Density | 1.560±0.10 g/cm3 |
Reference Reading
1.Strategies for the treatment of polymyxin B-resistant Acinetobacter baumannii infections.
Menegucci TC1, Albiero J1, Migliorini LB1, Alves JL1, Viana GF1, Mazucheli J1, Carrara-Marroni FE2, Cardoso CL1, Tognim MC3. Int J Antimicrob Agents. 2016 Apr 5. pii: S0924-8579(16)30022-X. doi: 10.1016/j.ijantimicag.2016.02.007. [Epub ahead of print]
In this study, the activity of meropenem (MEM), fosfomycin (FOF) and polymyxin B (PMB), alone and in combination, was analysed. In addition, optimisation of the pharmacodynamic index of MEM and FOF against six isolates of OXA-23-producing Acinetobacter baumannii (including three resistant to PMB) that were not clonally related was assessed. Antimicrobial combinations were evaluated by chequerboard analysis and were considered synergistic when the fractional inhibitory concentration index (FICI) was ≤0.5. Pharmacodynamic analyses of the MEM and FOF dosing schemes were performed by Monte Carlo simulation. The target pharmacodynamic index (%ƒT>MIC) for MEM and FOF was ≥40% and ≥70%, respectively, and a probability of target attainment (PTA) ≥0.9 was considered adequate. Among the PMB-resistant isolates, combinations of PMB+MEM and PMB+FOF+MEM showed the highest synergistic activity (FICI ≤0.125); isolates that were previously PMB-resistant were included in the susceptible category using CLSI interpretive criteria.
2.Dissemination of Extended-Spectrum β-Lactamase- and AmpC β-Lactamase-Producing Escherichia coli within the Food Distribution System of Ho Chi Minh City, Vietnam.
Nguyen do P1, Nguyen TA1, Le TH1, Tran NM1, Ngo TP1, Dang VC1, Kawai T2, Kanki M2, Kawahara R2, Jinnai M2, Yonogi S2, Hirai Y2, Yamamoto Y3, Kumeda Y2. Biomed Res Int. 2016;2016:8182096. doi: 10.1155/2016/8182096. Epub 2016 Feb 17.
To investigate the dissemination of ESBL/pAmpC-producing E. coli within the food distribution system of Ho Chi Minh City (HCMC), Vietnam, the prevalence of ESBL/pAmpC-producing E. coli strains in chicken meat, pork, beef, and fish/shrimp samples obtained from slaughterhouses, a wholesale market, and supermarkets was examined. Among the total of 330 collected food samples, ESBL/pAmpC-producing E. coli was detected in 150 samples (45.5%). The highest prevalence of these isolates was in chicken meat (76/82, 92.7%), followed by pork (32/92, 34.8%), beef (18/74, 34.3%), and fish/shrimp (24/82, 29.3%). A total of 342 strains of ESBL/pAmpC-producing E. coli were isolated from 150 positive food samples. The most prevalent genes responsible for ESBL or pAmpC activity belonged to the CTX-M-9 (110/342, 31.2%), CTX-M-1 (102/342, 29.8%), and CIT (118/342, 34.5%) groups. To our knowledge, this is the first report of the high occurrence of pAmpC (37.1%) in animal-based food in Vietnam.
3.Susceptibility of contemporary isolates to fosfomycin: a systematic review of the literature.
Vardakas KZ1, Legakis NJ2, Triarides N1, Falagas ME3. Int J Antimicrob Agents. 2016 Feb 24. pii: S0924-8579(16)00047-9. doi: 10.1016/j.ijantimicag.2016.02.001. [Epub ahead of print]
The aim of this review was to evaluate the susceptibility of contemporary Gram-positive and Gram-negative bacteria to fosfomycin. PubMed and Scopus databases were systematically searched to identify studies published in print or electronically from January 2010 until June 2015. In total, 84 studies were selected. Susceptibility to fosfomycin of Staphylococcus aureus ranged between 33.2% and 100% (frequency=91.7%, 95% confidence interval 88.7-94.9%), of Enterococcus spp. from 30% to 100% (Enterococcus faecium 92.6%, 85.2-100%; Enterococcus faecalis 96.8%, 92.5-100%), of extended-spectrum β-lactamase (ESBL)-producing Escherichia coli from 81% to 100% (95.1%, 94.3-95.9%), of ESBL-producing Klebsiella pneumoniae from 15% to 100% (83.8%, 78.7-89.4%) and of carbapenem-resistant (CR) K. pneumoniae from 39.2% to 100% (73.5%, 66.4-81.4%). Staphylococcus aureus (including meticillin-resistant strains) and E. coli (including ESBL-producing strains) were the most likely to be susceptible with low minimum inhibitory concentrations (MICs).
4.[Community-acquired febrile urinary tract infection caused by extended-spectrum beta-lactamase-producing bacteria in hospitalised infants].
Hernández Marco R1, Guillén Olmos E2, Bretón-Martínez JR3, Giner Pérez L4, Casado Sánchez B5, Fujkova J4, Salamanca Campos M4, Nogueira Coito JM5. Enferm Infecc Microbiol Clin. 2016 Mar 11. pii: S0213-005X(16)00072-0. doi: 10.1016/j.eimc.2016.01.012. [Epub ahead of print]
INTRODUCTION: Extended-spectrum beta-lactamase (ESBL) producing bacteria are infrequent pathogens of urinary tract infections in children. The objective of our study was to investigate the presence, clinically associated characteristics and risk factors for acquisition of urinary tract infection/acute pyelonephritis (UTI/APN) in hospitalised children <2years old caused by community-acquired ESBL.
5.The mechanism of action of fosfomycin (phosphonomycin)
Kahan, F.M., Kahan, J.S., Cassidy, P.J. and Kropp, H., 1974. Annals of the New York Academy of Sciences, 235(1), pp.364-386.
The discovery of fosfomycin, a new antibiotic produced by strains of Streptomyces, was announced under its former name hosphonomycin by Hendlin and colleagues in 1969.l The chemical structure shown in FIGURE 1 combines two unusual features: an epoxide ring, rare among antibiotics, and a carbon-phosphorus bond which is seen to occur here for the first time among the natural products of the bacteria.
6.Fosfomycin
Falagas, M.E., Vouloumanou, E.K., Samonis, G. and Vardakas, K.Z., 2016. Clinical Microbiology Reviews, 29(2), pp.321-347.
The treatment of bacterial infections suffers from two major problems: spread of multidrug-resistant (MDR) or extensively drug-resistant (XDR) pathogens and lack of development of new antibiotics active against such MDR and XDR bacteria. As a result, physicians have turned to older antibiotics, such as polymyxins, tetracyclines, and aminoglycosides. Lately, due to development of resistance to these agents, fosfomycin has gained attention, as it has remained active against both Gram-positive and Gram-negative MDR and XDR bacteria. New data of higher quality have become available, and several issues were clarified further. In this review, we summarize the available fosfomycin data regarding pharmacokinetic and pharmacodynamic properties, the in vitro activity against susceptible and antibiotic-resistant bacteria, mechanisms of resistance and development of resistance during treatment, synergy and antagonism with other antibiotics, clinical effectiveness, and adverse events. Issues that need to be studied further are also discussed.
7.The revival of fosfomycin
Michalopoulos, A.S., Livaditis, I.G. and Gougoutas, V., 2011. International journal of infectious diseases, 15(11), pp.e732-e739.
Fosfomycin, originally named phosphonomycin, was discovered in Spain in 1969. There are three forms of fosfomycin: fosfomycin tromethamine (a soluble salt) and fosfomycin calcium for oral use, and fosfomycin disodium for intravenous use. Fosfomycin is a bactericidal antibiotic that interferes with cell wall synthesis in both Gram-positive and Gram-negative bacteria by inhibiting the initial step involving phosphoenolpyruvate synthetase. It has a broad spectrum of activity against a wide range of Gram-positive and Gram-negative bacteria. It is highly active against Gram-positive pathogens such as Staphylococcus aureus and Enterococcus, and against Gram-negative bacteria such as Pseudomonas aeruginosa and Klebsiella pneumoniae. Its unique mechanism of action may provide a synergistic effect to other classes of antibiotics including beta-lactams, aminoglycosides, and fluoroquinolones. Oral fosfomycin is mainly used in the treatment of urinary tract infections, particularly those caused by Escherichia coli and Enterococcus faecalis. Intravenous fosfomycin has been administered in combination with other antibiotics for the treatment of nosocomial infections due to multidrug-resistant (MDR) Gram-positive and Gram-negative bacteria. Fosfomycin has good distribution into tissues, achieving clinically relevant concentrations in serum, kidneys, bladder wall, prostate, lungs, inflamed tissues, bone, cerebrospinal fluid, abscess fluid, and heart valves. Fosfomycin is well tolerated, with a low incidence of adverse events. Further randomized controlled trials are needed in order to evaluate the efficacy of intravenous fosfomycin for the management of nosocomial infections due to MDR pathogens.
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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 ╳
