Fosfomycin calcium | CAS#26016-98-8 | MurA inhibitor | isopentenyl mevalonate kinase inhibitor

MedKoo Cat#: 540143 | Name: Fosfomycin calcium

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Description:

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

Fosfomycin calcium is a MurA and isopentenyl mevalonate kinase inhibitor that prevents synthesis of bacterial cell walls. It also prevents aminoglycoside antibiotic-induced nephrotoxicity and lowers serum levels of TNF-α, IL-1β, and IL-6 in models of septic Pseudomonas infection.

Chemical Structure

Fosfomycin calcium

CAS#26016-98-8 (calcium)

Theoretical Analysis

MedKoo Cat#: 540143

Name: Fosfomycin calcium

CAS#: 26016-98-8 (calcium)

Chemical Formula: C3H5CaO4P

Exact Mass: 0.0000

Molecular Weight: 176.12

Elemental Analysis: C, 20.46; H, 2.86; Ca, 22.76; O, 36.34; P, 17.59

Price and Availability

Size	Price	Availability
5g	USD 350.00	2 Weeks
10g	USD 600.00	2 Weeks
25g	USD 950.00	2 Weeks

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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

Calcium fosfomycin; Calcium phosphonomycin; Fosmicin; Calcium phosphonomycin; NSC 758170; NSC758170; NSC-758170

IUPAC/Chemical Name

calcium ((2R,3S)-3-methyloxiran-2-yl)phosphonate

InChi Key

YMZJBJPWTXJQMR-LJUKVTEVSA-L

InChi Code

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

SMILES Code

O=P([O-])([C@@H]1[C@@H](O1)C)[O-].[Ca+2]

Appearance

Solid powder

Purity

>95% (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

>2 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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 176.12 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: 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. 2: Jiang H, Chen H, Cai N, Zou J, Ju X. Quantitative 31P-NMR spectroscopy for the determination of fosfomycin and impurity A in pharmaceutical products of fosfomycin sodium or calcium. Magn Reson Chem. 2015 Jun;53(6):454-9. doi: 10.1002/mrc.4224. Epub 2015 Apr 9. PubMed PMID: 25855198. 3: Matsumoto T, Muratani T, Nakahama C, Tomono K. Clinical effects of 2 days of treatment by fosfomycin calcium for acute uncomplicated cystitis in women. J Infect Chemother. 2011 Feb;17(1):80-6. doi: 10.1007/s10156-010-0092-2. Epub 2010 Aug 7. PubMed PMID: 20694571. 4: Fujita M, Tomo N, Abe M, Hosoi K, Sató T. Experimental studies on absorption, distribution and excretion of a new antibiotic, fosfomycin. II. Absorption of oral preparations of fosfomycin calcium salt in dogs (author's transl). Jpn J Antibiot. 1975 Jun;28(3):314-9. Japanese. PubMed PMID: 1152285. 5: Borsa F, Leroy A, Fillastre JP, Godin M, Moulin B. Comparative pharmacokinetics of tromethamine fosfomycin and calcium fosfomycin in young and elderly adults. Antimicrob Agents Chemother. 1988 Jun;32(6):938-41. PubMed PMID: 3415215; PubMed Central PMCID: PMC172313. 6: Valtz A, Martinetto P, Achino A, Angeretti A, Gaffodio AM, Ferrero F. [Distribution of calcium-fosfomycin, lysine-fosfomycin, ornithine-fosfomycin and arginine-fosfomycin in volunteers]. G Ital Chemioter. 1979 Jan-Dec;26(1-2):213-7. Italian. PubMed PMID: 122077. 7: Fujita M, Tomono N, Abe M, Hosoi K, Sato T. [Experimental studies on absorption, distribution and excretion of fosfomycin. I. Absorption distribution and excretion of fosfomycin calcium salt (author's transl)]. Jpn J Antibiot. 1975 Jun;28(3):309-13. Japanese. PubMed PMID: 1152284. 8: Fernández A, Lara C, Loste A, Marca MC. Efficacy of calcium fosfomycin for the treatment of experimental infections of broiler chickens with Escherichia coli O78:K80. Vet Res Commun. 2002 Aug;26(6):427-36. PubMed PMID: 12241095. 9: Yokota M, Suzuki H, Odaki M, Koeda T. [Effects of fosfomycin calcium and sodium salts on the visual and auditory organs (author's transl)]. Jpn J Antibiot. 1977 Nov;30(11):920-7. Japanese. PubMed PMID: 592494. 10: Webster GK, Bell RG. Gas chromatographic analysis of fosfomycin in plasma for pharmacokinetic analysis. J AOAC Int. 1999 May-Jun;82(3):620-4. PubMed PMID: 10367380. 11: Koeda T, Moriguchi M. [Effect of fosfomycin-calcium on reproductive performance of rat and rabbit: teratogenicity test (author's transl)]. Jpn J Antibiot. 1979 Apr;32(4):546-54. Japanese. PubMed PMID: 459085. 12: Pérez DS, Tapia MO, Soraci AL. Fosfomycin: Uses and potentialities in veterinary medicine. Open Vet J. 2014;4(1):26-43. Epub 2014 Mar 16. Review. PubMed PMID: 26623336; PubMed Central PMCID: PMC4629597. 13: Bergan T. Pharmacokinetic comparison between fosfomycin and other phosphonic acid derivatives. Chemotherapy. 1990;36 Suppl 1:10-8. PubMed PMID: 2085981. 14: Koeda T, Moriguchi M, Hata T. [Effect of fosfomycin-calcium on reproductive performance of rats. II. Fertility test (author's transl)]. Jpn J Antibiot. 1980 May;33(5):613-7. Japanese. PubMed PMID: 7431661. 15: Mayama T, Yokota M, Shimatani I, Ohyagi H. Analysis of oral fosfomycin calcium (Fosmicin) side-effects after marketing. Int J Clin Pharmacol Ther Toxicol. 1993 Feb;31(2):77-82. PubMed PMID: 8458680. 16: Hayashi I, Hasegawa H. [Reevaluation of current antimicrobials. Fosfomycin sodium/calcium]. Jpn J Antibiot. 1994 Jul;47(7):861-8. Review. Japanese. PubMed PMID: 7933518. 17: Krause R, Patruta S, Daxböck F, Fladerer P, Wenisch C. The effect of fosfomycin on neutrophil function. J Antimicrob Chemother. 2001 Feb;47(2):141-6. PubMed PMID: 11157896. 18: Bergan T. Degree of absorption, pharmacokinetics of fosfomycin trometamol and duration of urinary antibacterial activity. Infection. 1990;18 Suppl 2:S65-9. PubMed PMID: 2286464. 19: Woodruff HB, Mata JM, Hernández S, Mochales S, Rodríguez A, Stapley EO, Wallick H, Miller AK, Hendlin D. Fosfomycin: Laboratory studies. Chemotherapy. 1977;23 Suppl 1:1-22. PubMed PMID: 583866. 20: Gismondo MR, Romeo MA, Lo Bue AM, Chisari G, Nicoletti G. Microbiological basis for the use of fosfomycin trometamol as single-dose therapy for simple cystitis. Chemioterapia. 1986 Aug;5(4):278-82. PubMed PMID: 3094965.