Fosfomycin | CAS#23155-02-4 | antibiotic

MedKoo Cat#: 598716 | Name: Fosfomycin

Description:

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

Fosfomycin is an antibiotic produced by Streptomyces fradiae.

Chemical Structure

Fosfomycin

CAS#23155-02-4 (free acid)

Theoretical Analysis

MedKoo Cat#: 598716

Name: Fosfomycin

CAS#: 23155-02-4 (free acid)

Chemical Formula: C3H7O4P

Exact Mass: 138.0082

Molecular Weight: 138.05

Elemental Analysis: C, 26.10; H, 5.11; O, 46.35; P, 22.44

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.

Bulk Inquiry

Related CAS #

23155-02-4 (free acid) 26016-98-8 (calcium) 26469-67-0 (calcium hydrate) 26016-99-9 (sodium) 78964-85-9 (Tromethamine)

Synonym

Fosfomycin; Fosfonomycin; phosphomycin; Phosphonomycin; Fosfocina; Fosfomicina; Fosfomycine; MK-955; MK 955; MK955; Antibiotic 833A;

IUPAC/Chemical Name

((2R,3S)-3-methyloxiran-2-yl)phosphonic acid

InChi Key

YMDXZJFXQJVXBF-STHAYSLISA-N

InChi Code

InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1

SMILES Code

C[C@H]1[C@@H](P(O)(O)=O)O1

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 138.05 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.

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: Reffert JL, Smith WJ. Fosfomycin for the treatment of resistant gram-negative bacterial infections. Insights from the Society of Infectious Diseases Pharmacists. Pharmacotherapy. 2014 Aug;34(8):845-57. doi: 10.1002/phar.1434. Epub 2014 Apr 30. Review. PubMed PMID: 24782335. 2: Docobo-Pérez F, Drusano GL, Johnson A, Goodwin J, Whalley S, Ramos-Martín V, Ballestero-Tellez M, Rodriguez-Martinez JM, Conejo MC, van Guilder M, Rodríguez-Baño J, Pascual A, Hope WW. Pharmacodynamics of fosfomycin: insights into clinical use for antimicrobial resistance. Antimicrob Agents Chemother. 2015 Sep;59(9):5602-10. doi: 10.1128/AAC.00752-15. Epub 2015 Jun 29. PubMed PMID: 26124169; PubMed Central PMCID: PMC4538498. 3: Gardiner BJ, Mahony AA, Ellis AG, Lawrentschuk N, Bolton DM, Zeglinski PT, Frauman AG, Grayson ML. Is fosfomycin a potential treatment alternative for multidrug-resistant gram-negative prostatitis? Clin Infect Dis. 2014 Feb;58(4):e101-5. doi: 10.1093/cid/cit704. Epub 2013 Oct 28. PubMed PMID: 24170195. 4: Stock I. [Fosfomycin--its significance for treatment of diseases due to multidrug-resistant bacteria]. Med Monatsschr Pharm. 2015 Jan;38(1):4-11. Review. German. PubMed PMID: 26349119. 5: Keating GM. Fosfomycin trometamol: a review of its use as a single-dose oral treatment for patients with acute lower urinary tract infections and pregnant women with asymptomatic bacteriuria. Drugs. 2013 Nov;73(17):1951-66. doi: 10.1007/s40265-013-0143-y. Review. PubMed PMID: 24202878. 6: Montgomery AB, Vallance S, Abuan T, Tservistas M, Davies A. A randomized double-blind placebo-controlled dose-escalation phase 1 study of aerosolized amikacin and fosfomycin delivered via the PARI investigational eFlow® inline nebulizer system in mechanically ventilated patients. J Aerosol Med Pulm Drug Deliv. 2014 Dec;27(6):441-8. doi: 10.1089/jamp.2013.1100. PubMed PMID: 24383962; PubMed Central PMCID: PMC4273204. 7: Parker SL, Frantzeskaki F, Wallis SC, Diakaki C, Giamarellou H, Koulenti D, Karaiskos I, Lipman J, Dimopoulos G, Roberts JA. Population Pharmacokinetics of Fosfomycin in Critically Ill Patients. Antimicrob Agents Chemother. 2015 Oct;59(10):6471-6. doi: 10.1128/AAC.01321-15. Epub 2015 Aug 3. PubMed PMID: 26239990; PubMed Central PMCID: PMC4576076. 8: Grayson ML, Macesic N, Trevillyan J, Ellis AG, Zeglinski PT, Hewitt NH, Gardiner BJ, Frauman AG. Fosfomycin for Treatment of Prostatitis: New Tricks for Old Dogs. Clin Infect Dis. 2015 Oct 1;61(7):1141-3. doi: 10.1093/cid/civ436. Epub 2015 Jun 10. PubMed PMID: 26063723. 9: Michalopoulos AS, Livaditis IG, Gougoutas V. The revival of fosfomycin. Int J Infect Dis. 2011 Nov;15(11):e732-9. doi: 10.1016/j.ijid.2011.07.007. Epub 2011 Sep 25. Review. PubMed PMID: 21945848. 10: Tesh LD, Shaeer KM, Cho JC, Estrada SJ, Huang V, Bland CM, DiMondi VP, Potter AN, Hussein G, Bookstaver PB. Neisseria gonorrhoeae and fosfomycin: Past, present and future. Int J Antimicrob Agents. 2015 Sep;46(3):290-6. doi: 10.1016/j.ijantimicag.2015.05.007. Epub 2015 Jun 19. Review. PubMed PMID: 26145201. 11: Albur MS, Noel A, Bowker K, MacGowan A. The combination of colistin and fosfomycin is synergistic against NDM-1-producing Enterobacteriaceae in in vitro pharmacokinetic/pharmacodynamic model experiments. Int J Antimicrob Agents. 2015 Nov;46(5):560-7. doi: 10.1016/j.ijantimicag.2015.07.019. Epub 2015 Sep 5. PubMed PMID: 26387065. 12: Wu YJ, Zheng QC, Zhang JL, Chu WT, Cui YL, Wang Y, Zhang HX. Fosfomycin induced structural change in fosfomycin resistance kinases FomA: molecular dynamics and molecular docking studies. J Mol Model. 2014 May;20(5):2236. doi: 10.1007/s00894-014-2236-2. Epub 2014 Apr 27. PubMed PMID: 24770549. 13: Parker SL, Lipman J, Dimopoulos G, Roberts JA, Wallis SC. A validated method for the quantification of fosfomycin on dried plasma spots by HPLC-MS/MS: application to a pilot pharmacokinetic study in humans. J Pharm Biomed Anal. 2015 Nov 10;115:509-14. doi: 10.1016/j.jpba.2015.07.013. Epub 2015 Jul 19. PubMed PMID: 26299527. 14: Raz R. Fosfomycin: an old--new antibiotic. Clin Microbiol Infect. 2012 Jan;18(1):4-7. doi: 10.1111/j.1469-0691.2011.03636.x. Epub 2011 Sep 13. Review. PubMed PMID: 21914036. 15: Di X, Wang R, Liu B, Zhang X, Ni W, Wang J, Liang B, Cai Y, Liu Y. In vitro activity of fosfomycin in combination with colistin against clinical isolates of carbapenem-resistant Pseudomas aeruginosa. J Antibiot (Tokyo). 2015 Sep;68(9):551-5. doi: 10.1038/ja.2015.27. Epub 2015 Mar 25. PubMed PMID: 25805069. 16: Alrowais H, McElheny CL, Spychala CN, Sastry S, Guo Q, Butt AA, Doi Y. Fosfomycin Resistance in Escherichia coli, Pennsylvania, USA. Emerg Infect Dis. 2015 Nov;21(11):2045-7. doi: 10.3201/eid2111.150750. PubMed PMID: 26488485; PubMed Central PMCID: PMC4622254. 17: Parker S, Lipman J, Koulenti D, Dimopoulos G, Roberts JA. What is the relevance of fosfomycin pharmacokinetics in the treatment of serious infections in critically ill patients? A systematic review. Int J Antimicrob Agents. 2013 Oct;42(4):289-93. doi: 10.1016/j.ijantimicag.2013.05.018. Epub 2013 Jul 20. Review. PubMed PMID: 23880170. 18: Poeppl W, Lingscheid T, Bernitzky D, Donath O, Reznicek G, Zeitlinger M, Burgmann H. Assessing pharmacokinetics of different doses of fosfomycin in laboratory rats enables adequate exposure for pharmacodynamic models. Pharmacology. 2014;93(1-2):65-8. doi: 10.1159/000357569. Epub 2014 Feb 5. PubMed PMID: 24503567. 19: Soraci AL, Amanto F, Tapia MO, de la Torre E, Toutain PL. Exposure variability of fosfomycin administered to pigs in food or water: impact of social rank. Res Vet Sci. 2014 Feb;96(1):153-9. doi: 10.1016/j.rvsc.2013.12.003. Epub 2013 Dec 12. PubMed PMID: 24388282. 20: Garrigós C, Murillo O, Lora-Tamayo J, Verdaguer R, Tubau F, Cabellos C, Cabo J, Ariza J. Fosfomycin-daptomycin and other fosfomycin combinations as alternative therapies in experimental foreign-body infection by methicillin-resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2013 Jan;57(1):606-10. doi: 10.1128/AAC.01570-12. Epub 2012 Oct 22. PubMed PMID: 23089756; PubMed Central PMCID: PMC3535973.