Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C8H11N.C3H7O4P |
| Molecular Weight | 259.2387 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H]1O[C@@H]1P(O)(O)=O.C[C@@H](N)C2=CC=CC=C2
InChI
InChIKey=ODALAXKSIBESFV-PXRNWTNJSA-N
InChI=1S/C8H11N.C3H7O4P/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)/t7-;2-,3+/m10/s1
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 |
|---|---|---|
| Effects of fosfomycin and imipenem-cilastatin on the nephrotoxicity of vancomycin and cisplatin in rats. | 1999 Feb |
|
| [Aeromonas spp bacteremia: study of 12 cases and review of the literature]. | 2001 Apr |
|
| FosB, a cysteine-dependent fosfomycin resistance protein under the control of sigma(W), an extracytoplasmic-function sigma factor in Bacillus subtilis. | 2001 Apr |
|
| Practice guidelines for the treatment of uncomplicated cystitis. | 2001 Aug |
|
| The effect of fosfomycin on glycopeptide antibiotic-induced nephrotoxicity in rats. | 2001 Dec |
|
| Isoprene produced by leaves protects the photosynthetic apparatus against ozone damage, quenches ozone products, and reduces lipid peroxidation of cellular membranes. | 2001 Dec |
|
| [Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine]. | 2001 Feb |
|
| Asparagine 23 and aspartate 305 are essential residues in the active site of UDP-N-acetylglucosamine enolpyruvyl transferase from Enterobacter cloacae. | 2001 Feb 13 |
|
| Evaluation of a new preservation solution containing fosfomycin for 20-hour canine lung preservation. | 2001 Feb-Mar |
|
| Deep wound infection after vagus nerve stimulator implantation: treatment without removal of the device. | 2001 Jan |
|
| [Drug resistance of Staphylococcus aureus strains, isolated from children with intestinal dysbacteriosis]. | 2001 Jan-Feb |
|
| Protective effects of fosfomycin on cisplatin-induced nephrotoxicity in patients with lung cancer. | 2001 Mar |
|
| [Pattern of antimicrobial susceptibility in uropathogen isolates from children]. | 2001 Mar |
|
| Thermal stability of disodium and calcium phosphomycin and the effects of the excipients evaluated by thermal analysis. | 2001 Mar |
|
| Natural antibiotic susceptibility of recently established coryneform bacteria. | 2001 May |
|
| Natural antibiotic susceptibility of Klebsiella pneumoniae, K. oxytoca, K. planticola, K. ornithinolytica and K. terrigena strains. | 2001 May |
|
| Protein purification and function assignment of the epoxidase catalyzing the formation of fosfomycin. | 2001 May 16 |
|
| Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
| Sharpless asymmetric dihydroxylation of trans-propenylphosphonate by using a modified AD-mix-alpha and the synthesis of fosfomycin. | 2001 Nov 16 |
|
| Control of Salmonella enteritidis phage type 4 experimental infection by fosfomycin in newly hatched chicks. | 2001 Oct |
|
| [Acute cystitis in women. Current microbial sensitivity in our setting]. | 2001 Sep |
|
| Effect of phosphate transporter and methylation inhibitor drugs on the disposition of arsenate and arsenite in rats. | 2001 Sep |
|
| Cloning and sequencing of the gene, fmtC, which affects oxacillin resistance in methicillin-resistant Staphylococcus aureus. | 2001 Sep 11 |
|
| Therapy of uncomplicated urinary tract infections. | 2002 |
|
| 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 |
|
| Antibiotics as anti-inflammatory agents. | 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 |
|
| Fosfomycin inhibits neutrophil function via a protein kinase C-dependent signaling pathway. | 2002 Mar |
|
| In vitro susceptibility of four serotypes of enterohaemorrhagic Escherichia coli to antimicrobial agents. | 2002 May |
|
| [Rational use of medications in the treatment of urinary infections]. | 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 |
|
| Empirical treatment of adult postsurgical nosocomial meningitis. | 2002 Oct |
|
| 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 |
|
| 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
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
25383-07-7
Created by
admin on Sat Dec 16 07:02:06 GMT 2023 , Edited by admin on Sat Dec 16 07:02:06 GMT 2023
|
PRIMARY | |||
|
DTXSID80726231
Created by
admin on Sat Dec 16 07:02:06 GMT 2023 , Edited by admin on Sat Dec 16 07:02:06 GMT 2023
|
PRIMARY | |||
|
50V5RBU89I
Created by
admin on Sat Dec 16 07:02:06 GMT 2023 , Edited by admin on Sat Dec 16 07:02:06 GMT 2023
|
PRIMARY | |||
|
57416889
Created by
admin on Sat Dec 16 07:02:06 GMT 2023 , Edited by admin on Sat Dec 16 07:02:06 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD
