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

• ChemBase编号: 707
• 分子式: C3H7O4P
• 平均质量: 138.059041
• 单一同位素质量: 138.00819533
• SMILES: P(=O)(O)(O)[C@H]1O[C@H]1C
• Canonical SMILES: C[C@@H]1O[C@@H]1P(=O)(O)O
• InChI: InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1
• InChIKey: YMDXZJFXQJVXBF-STHAYSLISA-N

名称和登记号

名称

• IUPAC标准名: [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
• IUPAC传统名: fosfomycin
• 商标名: Monurol; Veramina
• 别名: Fosfomycin disodium salt; Fosfomycin sodium; Fosfocina; Fosfonomycin; Phosphomycin; phosphomycin disodium salt; Phosphonomycin; Fosfomycin

登记号

• CAS号: 23155-02-4
• PubChem SID: 160964170; 46506665
• PubChem CID: 446987

理论计算性质

JChem

• Acid pKa: 1.2504967
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): -3.0407646
• LogD (pH = 7.4): -3.1824315
• Log P: -0.7377749
• 摩尔折射率: 25.8737 cm^3
• 极化性: 10.712277 Å^3
• 极化表面积: 70.06 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.86
• LOG S: -0.47
• 溶解度: 4.69e+01 g/l

分子性质

理化性质

• 溶解度: 50 mg/mL (Sodium salt)
• 疏水性(logP): -1.6

详细说明

DrugBank - DB00828

• Drug Groups: approved
• Description: An antibiotic produced by Streptomyces fradiae. [PubChem]
• Indication: For the treatment of uncomplicated urinary tract infections (acute cystitis) in women due to susceptible strains of Escherichia coli and Enterococcus faecalis.
• Pharmacology: Fosfomycin is a broad spectrum antibiotic that concentrates in kidney and bladder and is used to treat uncomplicated urinary tract infections. Fosfomycin also reduces nephrotoxicity and ototoxicity of platinum-containing anti-tumor agents.
• Toxicity: LD₅₀>5 g/kg (rats). Side effects may include diarrhea
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: No transformation, excreted unchanged
• Absorption: Fosfomycin tromethamine is rapidly absorbed following oral administration and converted to fosfomycin. Oral bioavailability under fasting conditions is 37%. When given with food, oral bioavailability is reduced to 30%
• Half Life: 5.7 (± 2.8) hours. The elimination half-life is 40 hours in anuric patients undergoing hemodialysis.
• Protein Binding: 0% (not bound to plasma proteins)
• Elimination: Fosfomycin is excreted unchanged in both urine and feces.
• Distribution: * 136.1 ±44.1 L
• Clearance: * 16.9 +/- 3.5 L/hr
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com