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

• ChemBase编号: 133014
• 分子式: C3H5Na2O4P
• 平均质量: 182.022701
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: disodium [(2R,3S)-3-methyloxiran-2-yl]phosphonate
• IUPAC传统名: disodium fosfomycin(2-)
• 别名: (-)-(1R,2S)-(1,2-环氧丙基)膦酸; 磷霉素 二钠盐; 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

登记号

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

理论计算性质

• Acid pKa: 1.2504967
• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): -3.0407646
• LogD (pH = 7.4): -3.1824315
• Log P: -0.7377749
• 摩尔折射率: 23.6303 cm^3
• 极化性: 10.472997 Å^3
• 极化表面积: 75.72 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Water
• 外观: White to Off-White Solid
• 熔点: >270°C (dec.)
• 疏水性(logP): -0.425

安全信息

• 保存条件: -20°C Freezer
• RTECS编号: SZ7902000
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 纯度: 95%

详细说明

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.

参考文献

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