Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C8H11N.C3H7O4P.H2O |
| Molecular Weight | 277.254 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.C[C@@H]1O[C@@H]1P(O)(O)=O.C[C@@H](N)C2=CC=CC=C2
InChI
InChIKey=XDXCFDPDYZSCAG-YTBDAQBXSA-N
InChI=1S/C8H11N.C3H7O4P.H2O/c1-7(9)8-5-3-2-4-6-8;1-2-3(7-2)8(4,5)6;/h2-7H,9H2,1H3;2-3H,1H3,(H2,4,5,6);1H2/t7-;2-,3+;/m10./s1
| Molecular Formula | C8H11N |
| Molecular Weight | 121.1796 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | C3H7O4P |
| Molecular Weight | 138.059 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Fosfomycin (marketed under the trade names Monurol and Monuril) is a broad-spectrum antibiotic. Monurol (fosfomycin tromethamine) sachet contains fosfomycin tromethamine, a synthetic, broad spectrum, bactericidal antibiotic for oral administration. Monurol is indicated only for the treatment of uncomplicated urinary tract infections (acute cystitis) in women due to susceptible strains of Escherichia coli and Enterococcus faecalis. Fosfomycin is a phosphoenolpyruvate analogue produced by Streptomyces that irreversibly inhibits enolpyruvate transferase (MurA), which prevents the formation of N-acetylmuramic acid, an essential element of the peptidoglycan cell wall.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 100.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | MONUROL Approved UseMONUROL is indicated only for the treatment of uncomplicated urinary tract infections (acute cystitis) in women due to susceptible strains of Escherichia coli and Enterococcus faecalis. MONUROL is not indicated for the treatment of pyelonephritis or perinephric abscess. If persistence or reappearance of bacteriuria occurs after treatment with MONUROL, other therapeutic agents should be selected. Launch Date1996 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
26.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28630194 |
3 g single, oral dose: 3 g route of administration: Oral experiment type: SINGLE co-administered: |
FOSFOMYCIN TROMETHAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
191 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28630194 |
3 g single, oral dose: 3 g route of administration: Oral experiment type: SINGLE co-administered: |
FOSFOMYCIN TROMETHAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
9.04 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28630194 |
3 g single, oral dose: 3 g route of administration: Oral experiment type: SINGLE co-administered: |
FOSFOMYCIN TROMETHAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
100% |
unknown, unknown |
FOSFOMYCIN TROMETHAMINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
3 g 1 times / day single, oral Recommended Dose: 3 g, 1 times / day Route: oral Route: single Dose: 3 g, 1 times / day Sources: |
unhealthy, 32 Health Status: unhealthy Age Group: 32 Sex: M+F Sources: |
Disc. AE: Diarrhea, Erythema... AEs leading to discontinuation/dose reduction: Diarrhea Sources: Erythema Vomiting Rash Dry mouth |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Diarrhea | Disc. AE | 3 g 1 times / day single, oral Recommended Dose: 3 g, 1 times / day Route: oral Route: single Dose: 3 g, 1 times / day Sources: |
unhealthy, 32 Health Status: unhealthy Age Group: 32 Sex: M+F Sources: |
| Dry mouth | Disc. AE | 3 g 1 times / day single, oral Recommended Dose: 3 g, 1 times / day Route: oral Route: single Dose: 3 g, 1 times / day Sources: |
unhealthy, 32 Health Status: unhealthy Age Group: 32 Sex: M+F Sources: |
| Erythema | Disc. AE | 3 g 1 times / day single, oral Recommended Dose: 3 g, 1 times / day Route: oral Route: single Dose: 3 g, 1 times / day Sources: |
unhealthy, 32 Health Status: unhealthy Age Group: 32 Sex: M+F Sources: |
| Rash | Disc. AE | 3 g 1 times / day single, oral Recommended Dose: 3 g, 1 times / day Route: oral Route: single Dose: 3 g, 1 times / day Sources: |
unhealthy, 32 Health Status: unhealthy Age Group: 32 Sex: M+F Sources: |
| Vomiting | Disc. AE | 3 g 1 times / day single, oral Recommended Dose: 3 g, 1 times / day Route: oral Route: single Dose: 3 g, 1 times / day Sources: |
unhealthy, 32 Health Status: unhealthy Age Group: 32 Sex: M+F Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Structural basis of fosmidomycin action revealed by the complex with 2-C-methyl-D-erythritol 4-phosphate synthase (IspC). Implications for the catalytic mechanism and anti-malaria drug development. | 2003-05-16 |
|
| Inhibition of paclitaxel and baccatin III accumulation by mevinolin and fosmidomycin in suspension cultures of Taxus baccata. | 2003-03-06 |
|
| [Staphylococcus aureus meningitis with intermediate sensitivity to glycopeptides. Therapeutic indications]. | 2003-02-08 |
|
| Life-threatening infantile diarrhea from fluoroquinolone-resistant Salmonella enterica typhimurium with mutations in both gyrA and parC. | 2003-02 |
|
| Urinary tract infection: traditional pharmacologic therapies. | 2003-02 |
|
| Identification and disruption of btlA, a locus involved in bile tolerance and general stress resistance in Listeria monocytogenes. | 2003-01-21 |
|
| Moellerella wisconsensis: identification, natural antibiotic susceptibility and its dependency on the medium applied. | 2003-01 |
|
| An international survey of the antimicrobial susceptibility of pathogens from uncomplicated urinary tract infections: the ECO.SENS Project. | 2003-01 |
|
| Structure and function of the Mur enzymes: development of novel inhibitors. | 2003-01 |
|
| Fosmidomycin for malaria. | 2002-12-14 |
|
| Mechanistic studies of HPP epoxidase: configuration of the substrate governs its enzymatic fate. | 2002-12-02 |
|
| [Antibacterial activities of fosfomycin against several fresh clinical isolates--comparison of the test methods for antibacterial activity]. | 2002-12 |
|
| Biofilm testing of Staphylococcus epidermidis clinical isolates: low performance of vancomycin in relation to other antibiotics. | 2002-12 |
|
| [Rhône-Alpes observatory of Streptococcus pneumoniae in 1999: 35 cases of meningitis]. | 2002-12 |
|
| Time- and dose-dependent effect of fosfomycin on suppression of infection-induced endotoxin shock in mice. | 2002-12 |
|
| Penetration of fosfomycin into the parenchyma of human brain: a case study in three patients. | 2002-11 |
|
| Elucidation of the methylerythritol phosphate pathway for isoprenoid biosynthesis in bacteria and plastids. A metabolic milestone achieved through genomics. | 2002-11 |
|
| Natural antibiotic susceptibility of Enterobacter spp., with special reference to Enterobacter aerogenes and Enterobacter intermedius strains. | 2002-10 |
|
| Empirical treatment of adult postsurgical nosocomial meningitis. | 2002-10 |
|
| On-line analysis of the (13)CO(2) labeling of leaf isoprene suggests multiple subcellular origins of isoprene precursors. | 2002-10 |
|
| Crystal structure of a genomically encoded fosfomycin resistance protein (FosA) at 1.19 A resolution by MAD phasing off the L-III edge of Tl(+). | 2002-09-18 |
|
| On the transformation of (S)-2-hydroxypropylphosphonic acid into fosfomycin in Streptomyces fradiae--a unique method of epoxide ring formation. | 2002-09-02 |
|
| Natural antibiotic susceptibility of Enterobacter amnigenus, Enterobacter cancerogenus, Enterobacter gergoviae and Enterobacter sakazakii strains. | 2002-09 |
|
| Role of fosfomycin in a synergistic combination with ofloxacin against Pseudomonas aeruginosa growing in a biofilm. | 2002-09 |
|
| Mevalonate and nonmevalonate pathways for the biosynthesis of isoprene units. | 2002-08 |
|
| Efficacy of calcium fosfomycin for the treatment of experimental infections of broiler chickens with Escherichia coli O78:K80. | 2002-08 |
|
| Comparative pulsed-field gel electrophoresis typing of gentamicin-resistant and -susceptible methicillin-resistant Staphylococcus aureus strains isolated in France between 1991 and 1998. Changes in antibiotic susceptibility. | 2002-08 |
|
| Urinary tract infection: traditional pharmacologic therapies. | 2002-07-08 |
|
| Susceptibility of Streptococcus mutans and Streptococcus sobrinus to cell wall inhibitors and development of a novel selective medium for S. sobrinus. | 2002-06-18 |
|
| In-vitro susceptibility of quinolone-resistant clinical isolates of Escherichia coli to fosfomycin trometamol. | 2002-06 |
|
| [Treatment in initial stage of VTEC infection]. | 2002-06 |
|
| [Indicators for early diagnosis of enterohemorrhagic Escherichia coli infection and methods for final diagnosis]. | 2002-06 |
|
| Antisense and chemical suppression of the nonmevalonate pathway affects ent-kaurene biosynthesis in Arabidopsis. | 2002-06 |
|
| [Rational use of medications in the treatment of urinary infections]. | 2002-05-15 |
|
| Flow injection spectrophotometric determination of the antibiotic fosfomycin in pharmaceutical products and urine samples after on-line thermal-induced digestion. | 2002-05-15 |
|
| In vitro susceptibility of four serotypes of enterohaemorrhagic Escherichia coli to antimicrobial agents. | 2002-05 |
|
| Emergence of vancomycin-intermediate Staphylococcus aureus and S. sciuri, Greece. | 2002-05 |
|
| In vitro susceptibility of vancomycin-resistant enterococci (VRE) to fosfomycin. | 2002-04 |
|
| EPR study of substrate binding to the Mn(II) active site of the bacterial antibiotic resistance enzyme FosA: a better way to examine Mn(II). | 2002-03-13 |
|
| A pathway-specific cell based screening system to detect bacterial cell wall inhibitors. | 2002-03 |
|
| Fosfomycin inhibits neutrophil function via a protein kinase C-dependent signaling pathway. | 2002-03 |
|
| Effectiveness of fosfomycin combined with other antimicrobial agents against multidrug-resistant Pseudomonas aeruginosa isolates using the efficacy time index assay. | 2002-03 |
|
| Time-dependent toxicity in the long-term inhibition assay with Vibrio fischeri. | 2002-02 |
|
| Antibiotics as anti-inflammatory agents. | 2002-01 |
|
| Pseudo-septic meningeal reaction after intradural glucocorticoid therapy for sciatica. | 2002-01 |
|
| Microbiological evaluation of a commercial transport system for urine samples. | 2002 |
|
| Therapy of uncomplicated urinary tract infections. | 2002 |
|
| [Fosfomycin: an underrated antibiotic for urinary tract infections due to Escherichia coli]. | 2001-12 |
|
| Practice guidelines for the treatment of uncomplicated cystitis. | 2001-08 |
|
| [The epoxidation of cis-propenylphophonic acid to fosfomycin by Pencillium sp]. | 2001-06 |
Sample Use Guides
Urinary tract infections, uncomplicated: Oral: Females: Single dose of 3 g in 3 to 4 oz (90 to 120 mL) of water
Complicated UTI (off-label): Males: Oral: 3 g every 2 to 3 days for 3 doses
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 21:43:11 GMT 2025
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on
Mon Mar 31 21:43:11 GMT 2025
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| Record UNII |
6226IMZ7MC
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
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91617671
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65794-75-4
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6226IMZ7MC
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DTXSID701349787
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