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Merck
CN

P7902

Phosphomycin calcium salt

Synonym(s):

(−)-(1R,2S)-(1,2-Epoxypropyl)phosphonic acid, Fosfomycin calcium salt, Phosphonomycin

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About This Item

Linear Formula:
C3H5O4PCa
CAS Number:
26016-98-8
Molecular Weight:
176.12
UNSPSC Code:
51101500
PubChem Substance ID:
24898888
EC Number:
247-408-7
MDL number:
MFCD00070095

Key Documents

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InChI key

YMZJBJPWTXJQMR-UHFFFAOYSA-L

InChI

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

SMILES string

[Ca++].CC1OC1P([O-])([O-])=O

solubility

1 M HCl: soluble 50 mg/mL

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria

mode of action

cell wall synthesis | interferes

storage temp.

2-8°C

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Application

Phosphomycin, also known as Fosfomycin, is an antibiotic produced by Streptomyces fradiae. It is used to treat uncomplicated urinary tract infections and to reduce nephrotoxicity and ototoxicity of platinum-containing anti-tumor agents. It is used to study resistance proteins in Bacillus subtilis and Mycobacterium tuberculosis. It is a potential treatment for bronchiectasis.

Biochem/physiol Actions

Fosfomycin is a phosphoenolpyruvate analog. It irreversibly inhibits enolpyruvate transferase (MurA). Therefore, the producion of N-acetylmuramic acid, an essential element of the peptidoglycan cell wall is inhibited.
Phosphomycin calcium salt blocks the formation or N-acetylmuramic acid by inhibiting UDP-Nacetylglucosamine 3-enolpyruvate transferase (MurA).

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Storage Class

13 - Non Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

涉药品监管产品
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Certificates of Analysis (COA)

Lot/Batch Number
SLBH1888V
081M1279V
021M0122V
069K1699
117K1313

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David L MacLeod et al.
The Journal of antimicrobial chemotherapy, 64(4), 829-836 (2009-08-15)
To compare the in vitro and in vivo activities of a 4:1 (w/w) fosfomycin/tobramycin combination (FTI) with those of fosfomycin and tobramycin alone against cystic fibrosis (CF) and non-CF bronchiectasis pathogens. Clinical isolates of CF Pseudomonas aeruginosa, Staphylococcus aureus, Haemophilus
M Cao et al.
Journal of bacteriology, 183(7), 2380-2383 (2001-03-13)
We demonstrate that the Bacillus subtilis fosB(yndN) gene encodes a fosfomycin resistance protein. Expression of fosB requires sigma(W), and both fosB and sigW mutants are fosfomycin sensitive. FosB is a metallothiol transferase related to the FosA class of Mn(2+)-dependent glutathione
K A De Smet et al.
Microbiology (Reading, England), 145 ( Pt 11), 3177-3184 (1999-12-10)
Mycobacterium tuberculosis has innate resistance to a range of broad-spectrum antimicrobial agents. This may in part reflect the relative impermeability of the mycobacterial cell wall, but additional specific mechanisms may also be important. In the case of fosfomycin, it has

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