disodium [(2R,3S)-3-methyloxiran-2-yl]phosphonate

• ChemBase ID: 133014
• Molecular Formular: C3H5Na2O4P
• Molecular Mass: 182.022701
• Monoisotopic Mass: 181.97208383
• SMILES: C[C@H]1[C@H](O1)P(=O)([O-])[O-].[Na+].[Na+]
• Canonical SMILES: C[C@@H]1O[C@@H]1P(=O)([O-])[O-].[Na+].[Na+]
• InChI: InChI=1S/C3H7O4P.2Na/c1-2-3(7-2)8(4,5)6;;/h2-3H,1H3,(H2,4,5,6);;/q;2*+1/p-2/t2-,3+;;/m0../s1
• InChIKey: QZIQJIKUVJMTDG-JSTPYPERSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(2R,3S)-3-methyloxiran-2-yl]phosphonate
• IUPAC Traditional name: disodium fosfomycin(2-)
• Synonyms: Phosphomycin Disodium Salt; Disodium (1R,2S)-(1,2-epoxypropyl)phosphonate; Fosfomycin Disodium Salt; disodium [(2R,3S)-3-methyloxiran-2-yl]phosphonate; Fosfomycin; Phosphonomycin; Phosphomycin disodium salt; (-)-(1R,2S)-(1,2-环氧丙基)膦酸; 磷霉素 二钠盐

Database IDs

• CAS Number: 26016-99-9
• EC Number: 247-409-2
• MDL Number: MFCD22741288
• Beilstein Number: 4604425
• PubChem SID: 162227291; 24278640
• PubChem CID: 73491

CALCULATED PROPERTIES

• Acid pKa: 1.2504967
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -3.0407646
• LogD (pH = 7.4): -3.1824315
• Log P: -0.7377749
• Molar Refractivity: 23.6303 cm^3
• Polarizability: 10.472997 Å^3
• Polar Surface Area: 75.72 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: >270°C (dec.)
• Hydrophobicity(logP): -0.425

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: SZ7902000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%

DETAILS

Sigma Aldrich - P5396

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 for susceptibility studies of Klebsiella pneumoniae1 and to study in vitro susceptibility testing procedures for fosfomycin tromethamine2.
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.
聚集在肾脏和膀胱中的抗生素；降低含铂抗肿瘤制剂的肾毒性和耳毒性。磷霉素可以抑制 UDP-GlcNAc 烯醇式丙酮酸转移酶 (MurA)（细菌细胞壁生物合成中的酶）。

Toronto Research Chemicals - F727500

Antibiotic.

REFERENCES

• Goto, M., et al.: Antimicrob. Agents Chemother., 20, 393 (1981)