Fosfomycin

Basic Info

Common NameFosfomycin(F05840)
2D Structure
FRCD IDF05840
CAS Number23155-02-4
PubChem CID446987
FormulaC3H7O4P
IUPAC Name

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

InChI Key

YMDXZJFXQJVXBF-STHAYSLISA-N

InChI

InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1

Canonical SMILES

CC1C(O1)P(=O)(O)O

Isomeric SMILES

C[C@H]1[C@H](O1)P(=O)(O)O

Synonyms
        
            Phosphonomycin
        
            Phosphonemycin
        
            FOSFOMYCIN
        
            phosphomycin
        
            23155-02-4
        
            Fosfomycin sodium
        
            Veramina
        
            Fosfonomycin
        
            Fosfocina
        
            [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
Classifies
                

                  
                    Predicted: Pollutant
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassOrganic phosphonic acids and derivatives
SubclassOrganic phosphonic acids
Intermediate Tree NodesNot available
Direct ParentOrganic phosphonic acids
Alternative Parents
Molecular FrameworkAliphatic heteromonocyclic compounds
SubstituentsOrganophosphonic acid - Oxacycle - Organoheterocyclic compound - Oxirane - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organophosphorus compound - Organooxygen compound - Aliphatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.

Properties

Property NameProperty Value
Molecular Weight138.059
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Complexity138
Monoisotopic Mass138.008
Exact Mass138.008
XLogP-1.4
Formal Charge0
Heavy Atom Count8
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9382
Human Intestinal AbsorptionHIA-0.5000
Caco-2 PermeabilityCaco2-0.6652
P-glycoprotein SubstrateNon-substrate0.7234
P-glycoprotein InhibitorNon-inhibitor0.8938
Non-inhibitor0.9878
Renal Organic Cation TransporterNon-inhibitor0.9505
Distribution
Subcellular localizationMitochondria0.7256
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7514
CYP450 2D6 SubstrateNon-substrate0.8332
CYP450 3A4 SubstrateNon-substrate0.6513
CYP450 1A2 InhibitorNon-inhibitor0.8492
CYP450 2C9 InhibitorNon-inhibitor0.8551
CYP450 2D6 InhibitorNon-inhibitor0.9202
CYP450 2C19 InhibitorNon-inhibitor0.8016
CYP450 3A4 InhibitorNon-inhibitor0.9624
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9440
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9456
Non-inhibitor0.9491
AMES ToxicityNon AMES toxic0.6575
CarcinogensNon-carcinogens0.6059
Fish ToxicityLow FHMT0.8685
Tetrahymena Pyriformis ToxicityLow TPT0.5356
Honey Bee ToxicityHigh HBT0.7495
BiodegradationNot ready biodegradable0.8940
Acute Oral ToxicityIII0.5485
Carcinogenicity (Three-class)Non-required0.5914
Model Value Unit
Absorption
Aqueous solubility-1.7914LogS
Caco-2 Permeability-0.2359LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5802LD50, mol/kg
Fish Toxicity2.1253pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.3511pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
PerciformesJapan0.05ppm
MilkJapan0.05ppm
Cattle,Edible OffalJapan0.5ppm
Cattle,KidneyJapan0.5ppm
Cattle,LiverJapan0.5ppm
Cattle,FatJapan0.5ppm
Cattle,MuscleJapan0.5ppm

References

TitleJournalDatePubmed ID
Renal function in patients with non-dialysis chronic kidney disease receivingintravenous ferric carboxymaltose: an analysis of the randomized FIND-CKD trial.BMC Nephrol2017 Jan 1728095881
East and West African milk products are reservoirs for human and livestock-associated Staphylococcus aureus.Food Microbiol2017 Aug28400021
Clinical efficacy of ferric carboxymaltose treatment in patients with restlesslegs syndrome.Sleep Med2016 Sep27823710
Effect of antibiotics on cellular stress generated in Shiga toxin-producing Escherichia coli O157:H7 and non-O157 biofilms.Toxicol In Vitro2015 Oct26130220
Optimizing iron delivery in the management of anemia: patient considerations and the role of ferric carboxymaltose.Drug Des Devel Ther2014 Dec 1125525337
Comparative review of the safety and efficacy of ferric carboxymaltose versusstandard medical care for the treatment of iron deficiency anemia in bariatricand gastric surgery patients.Obes Surg2013 Sep23553506
Ferric carboxymaltose prevents recurrence of anemia in patients with inflammatorybowel disease.Clin Gastroenterol Hepatol2013 Mar23078888
Hepcidin levels predict nonresponsiveness to oral iron therapy in patients withiron deficiency anemia.Am J Hematol2013 Feb23335357
Penetration of fosfomycin into IPEC-J2 cells in the presence or absence of deoxynivalenol.PLoS One201324040387
Serotype, Shiga toxin (Stx) type, and antimicrobial resistance of Stx-producing Escherichia coli isolated from humans in Shizuoka Prefecture, Japan (2003-2007).Jpn J Infect Dis201222627299
Antimicrobial resistance patterns of Shiga toxin-producing Escherichia coli O157:H7 and O157:H7- from different origins.Microb Drug Resist2007 Spring17536933
[Antimicrobial susceptibility of shiga toxin producing E coli (STEC) strains isolated from human infections and food].Rev Med Chil2004 Oct15631209