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23155-02-4 molecular structure
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[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid

ChemBase ID: 707
Molecular Formular: C3H7O4P
Molecular Mass: 138.059041
Monoisotopic Mass: 138.00819533
SMILES and InChIs

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

Cite this record

CBID:707 http://www.chembase.cn/molecule-707.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
[(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
IUPAC Traditional name
fosfomycin
Brand Name
Monurol
Veramina
Synonyms
Fosfomycin disodium salt
Fosfomycin sodium
Fosfocina
Fosfonomycin
Phosphomycin
phosphomycin disodium salt
Phosphonomycin
Fosfomycin
CAS Number
23155-02-4
PubChem SID
160964170
46506665
PubChem CID
446987

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 1.2504967  H Acceptors
H Donor LogD (pH = 5.5) -3.0407646 
LogD (pH = 7.4) -3.1824315  Log P -0.7377749 
Molar Refractivity 25.8737 cm3 Polarizability 10.712277 Å3
Polar Surface Area 70.06 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.86  LOG S -0.47 
Solubility (Water) 4.69e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
50 mg/mL (Sodium salt) expand Show data source
Hydrophobicity(logP)
-1.6 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00828 external link
Item Information
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

REFERENCES

REFERENCES

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PATENTS

PATENTS

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