Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C3H6O4P.Na |
| Molecular Weight | 160.0409 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].C[C@@H]1O[C@@H]1[P@](O)([O-])=O
InChI
InChIKey=JHXHBFDOOUMZSP-LJUKVTEVSA-M
InChI=1S/C3H7O4P.Na/c1-2-3(7-2)8(4,5)6;/h2-3H,1H3,(H2,4,5,6);/q;+1/p-1/t2-,3+;/m0./s1
| Molecular Formula | C3H6O4P |
| Molecular Weight | 137.0511 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| 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: Page: MON-US-02 |
unhealthy, 32 n = 426 Health Status: unhealthy Condition: Infection Age Group: 32 Sex: M+F Population Size: 426 Sources: Page: MON-US-02 |
Disc. AE: Diarrhea, Erythema... AEs leading to discontinuation/dose reduction: Diarrhea Sources: Page: MON-US-02Erythema 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: Page: MON-US-02 |
unhealthy, 32 n = 426 Health Status: unhealthy Condition: Infection Age Group: 32 Sex: M+F Population Size: 426 Sources: Page: MON-US-02 |
| 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: Page: MON-US-02 |
unhealthy, 32 n = 426 Health Status: unhealthy Condition: Infection Age Group: 32 Sex: M+F Population Size: 426 Sources: Page: MON-US-02 |
| 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: Page: MON-US-02 |
unhealthy, 32 n = 426 Health Status: unhealthy Condition: Infection Age Group: 32 Sex: M+F Population Size: 426 Sources: Page: MON-US-02 |
| 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: Page: MON-US-02 |
unhealthy, 32 n = 426 Health Status: unhealthy Condition: Infection Age Group: 32 Sex: M+F Population Size: 426 Sources: Page: MON-US-02 |
| 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: Page: MON-US-02 |
unhealthy, 32 n = 426 Health Status: unhealthy Condition: Infection Age Group: 32 Sex: M+F Population Size: 426 Sources: Page: MON-US-02 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Practice guidelines for the treatment of uncomplicated cystitis. | 2001 Aug |
|
| [Fosfomycin: an underrated antibiotic for urinary tract infections due to Escherichia coli]. | 2001 Dec |
|
| [The epoxidation of cis-propenylphophonic acid to fosfomycin by Pencillium sp]. | 2001 Jun |
|
| Microbiological evaluation of a commercial transport system for urine samples. | 2002 |
|
| Therapy of uncomplicated urinary tract infections. | 2002 |
|
| In vitro susceptibility of vancomycin-resistant enterococci (VRE) to fosfomycin. | 2002 Apr |
|
| Mevalonate and nonmevalonate pathways for the biosynthesis of isoprene units. | 2002 Aug |
|
| Efficacy of calcium fosfomycin for the treatment of experimental infections of broiler chickens with Escherichia coli O78:K80. | 2002 Aug |
|
| 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 Aug |
|
| [Antibacterial activities of fosfomycin against several fresh clinical isolates--comparison of the test methods for antibacterial activity]. | 2002 Dec |
|
| Biofilm testing of Staphylococcus epidermidis clinical isolates: low performance of vancomycin in relation to other antibiotics. | 2002 Dec |
|
| [Rhône-Alpes observatory of Streptococcus pneumoniae in 1999: 35 cases of meningitis]. | 2002 Dec |
|
| Time- and dose-dependent effect of fosfomycin on suppression of infection-induced endotoxin shock in mice. | 2002 Dec |
|
| Fosmidomycin for malaria. | 2002 Dec 14 |
|
| Mechanistic studies of HPP epoxidase: configuration of the substrate governs its enzymatic fate. | 2002 Dec 2 |
|
| Time-dependent toxicity in the long-term inhibition assay with Vibrio fischeri. | 2002 Feb |
|
| Antibiotics as anti-inflammatory agents. | 2002 Jan |
|
| Pseudo-septic meningeal reaction after intradural glucocorticoid therapy for sciatica. | 2002 Jan |
|
| Urinary tract infection: traditional pharmacologic therapies. | 2002 Jul 8 |
|
| In-vitro susceptibility of quinolone-resistant clinical isolates of Escherichia coli to fosfomycin trometamol. | 2002 Jun |
|
| [Treatment in initial stage of VTEC infection]. | 2002 Jun |
|
| [Indicators for early diagnosis of enterohemorrhagic Escherichia coli infection and methods for final diagnosis]. | 2002 Jun |
|
| Antisense and chemical suppression of the nonmevalonate pathway affects ent-kaurene biosynthesis in Arabidopsis. | 2002 Jun |
|
| A pathway-specific cell based screening system to detect bacterial cell wall inhibitors. | 2002 Mar |
|
| Fosfomycin inhibits neutrophil function via a protein kinase C-dependent signaling pathway. | 2002 Mar |
|
| Effectiveness of fosfomycin combined with other antimicrobial agents against multidrug-resistant Pseudomonas aeruginosa isolates using the efficacy time index assay. | 2002 Mar |
|
| 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 Mar 13 |
|
| In vitro susceptibility of four serotypes of enterohaemorrhagic Escherichia coli to antimicrobial agents. | 2002 May |
|
| Emergence of vancomycin-intermediate Staphylococcus aureus and S. sciuri, Greece. | 2002 May |
|
| [Rational use of medications in the treatment of urinary infections]. | 2002 May 15 |
|
| Flow injection spectrophotometric determination of the antibiotic fosfomycin in pharmaceutical products and urine samples after on-line thermal-induced digestion. | 2002 May 15 |
|
| Susceptibility of Streptococcus mutans and Streptococcus sobrinus to cell wall inhibitors and development of a novel selective medium for S. sobrinus. | 2002 May-Jun |
|
| Penetration of fosfomycin into the parenchyma of human brain: a case study in three patients. | 2002 Nov |
|
| Elucidation of the methylerythritol phosphate pathway for isoprenoid biosynthesis in bacteria and plastids. A metabolic milestone achieved through genomics. | 2002 Nov |
|
| Natural antibiotic susceptibility of Enterobacter spp., with special reference to Enterobacter aerogenes and Enterobacter intermedius strains. | 2002 Oct |
|
| Empirical treatment of adult postsurgical nosocomial meningitis. | 2002 Oct |
|
| On-line analysis of the (13)CO(2) labeling of leaf isoprene suggests multiple subcellular origins of isoprene precursors. | 2002 Oct |
|
| Natural antibiotic susceptibility of Enterobacter amnigenus, Enterobacter cancerogenus, Enterobacter gergoviae and Enterobacter sakazakii strains. | 2002 Sep |
|
| Role of fosfomycin in a synergistic combination with ofloxacin against Pseudomonas aeruginosa growing in a biofilm. | 2002 Sep |
|
| 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 Sep 18 |
|
| On the transformation of (S)-2-hydroxypropylphosphonic acid into fosfomycin in Streptomyces fradiae--a unique method of epoxide ring formation. | 2002 Sep 2 |
|
| Life-threatening infantile diarrhea from fluoroquinolone-resistant Salmonella enterica typhimurium with mutations in both gyrA and parC. | 2003 Feb |
|
| Urinary tract infection: traditional pharmacologic therapies. | 2003 Feb |
|
| [Staphylococcus aureus meningitis with intermediate sensitivity to glycopeptides. Therapeutic indications]. | 2003 Feb 8 |
|
| Moellerella wisconsensis: identification, natural antibiotic susceptibility and its dependency on the medium applied. | 2003 Jan |
|
| An international survey of the antimicrobial susceptibility of pathogens from uncomplicated urinary tract infections: the ECO.SENS Project. | 2003 Jan |
|
| Structure and function of the Mur enzymes: development of novel inhibitors. | 2003 Jan |
|
| Identification and disruption of btlA, a locus involved in bile tolerance and general stress resistance in Listeria monocytogenes. | 2003 Jan 21 |
|
| Inhibition of paclitaxel and baccatin III accumulation by mevinolin and fosmidomycin in suspension cultures of Taxus baccata. | 2003 Mar 6 |
|
| 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 May 16 |
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
on
Edited
Fri Dec 15 15:21:28 GMT 2023
by
admin
on
Fri Dec 15 15:21:28 GMT 2023
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| Record UNII |
0F86SNQ5NQ
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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33996-10-0
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0F86SNQ5NQ
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10197820
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DTXSID50187597
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