U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C3H7O4P
Molecular Weight 138.059
Optical Activity ( - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FOSFOMYCIN

SMILES

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

InChI

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

HIDE SMILES / InChI

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

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
MONUROL

Approved Use

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. 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 Date

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
26.8 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
191 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
9.04 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
unknown, unknown
FOSFOMYCIN TROMETHAMINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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
Erythema
Vomiting
Rash
Dry mouth
Sources: Page: MON-US-02
AEs

AEs

AESignificanceDosePopulation
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
PubMed

PubMed

TitleDatePubMed
Practice guidelines for the treatment of uncomplicated cystitis.
2001 Aug
Campylobacter, Salmonella, Shigella and Escherichia coli in live and dressed poultry from metropolitan accra.
2001 Dec 4
[The epoxidation of cis-propenylphophonic acid to fosfomycin by Pencillium sp].
2001 Jun
[Effects of erythromycin and fosfomycin on Pseudomonas aeruginosa biofilm in vitro].
2001 Jun
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
[Urinary infection caused by Oligella urethralis].
2001 Nov 30
[Acute cystitis in women. Current microbial sensitivity in our setting].
2001 Sep
Cloning and sequencing of the gene, fmtC, which affects oxacillin resistance in methicillin-resistant Staphylococcus aureus.
2001 Sep 11
Microbiological evaluation of a commercial transport system for urine samples.
2002
Therapy of uncomplicated urinary tract infections.
2002
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
Antibiotics as anti-inflammatory agents.
2002 Jan
Modulatory effect of macrolide antibiotics on the Th1- and Th2-type cytokine production.
2002 Jan
E. coli MEP synthase: steady-state kinetic analysis and substrate binding.
2002 Jan 8
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
Effectiveness of fosfomycin combined with other antimicrobial agents against multidrug-resistant Pseudomonas aeruginosa isolates using the efficacy time index assay.
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
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
Patents

Sample Use Guides

In Vivo Use Guide
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
Fosfomycin MIC50 and MIC90 values were 16 and 128 ug/mL for the 38 ceftazidime-nonsusceptible Enterobacter isolates and 64 and 128 ug/mL for the 15 ceftazidime-nonsusceptible P. aeruginosa isolates, respectively.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:26:30 GMT 2023
Edited
by admin
on Fri Dec 15 16:26:30 GMT 2023
Record UNII
2N81MY12TE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FOSFOMYCIN
INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
FOSFOMYCIN [JAN]
Common Name English
PHOSPHONIC ACID, (3-METHYLOXIRANYL)-, (2R-CIS)-
Common Name English
fosfomycin [INN]
Common Name English
FOSFOMYCIN [USAN]
Common Name English
J01XX01
Code English
FOSFOMYCIN [MART.]
Common Name English
ZTI-01
Code English
(-)-(1R,2S)-(1,2-EPOXYPROPYL)PHOSPHONIC ACID
Systematic Name English
Fosfomycin [WHO-DD]
Common Name English
FOSFOMYCIN [VANDF]
Common Name English
FOSFOMYCIN [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC J01XX01
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
NCI_THESAURUS C255
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
WHO-VATC QJ01XX01
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
LIVERTOX NBK547912
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
FDA ORPHAN DRUG 271908
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL1757
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
CAS
23155-02-4
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
DRUG BANK
DB00828
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
MERCK INDEX
m5551
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY Merck Index
INN
3014
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
CHEBI
62247
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
CHEBI
62419
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
DRUG CENTRAL
1243
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
RXCUI
4550
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY RxNorm
CHEBI
28915
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
DAILYMED
2N81MY12TE
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
MESH
D005578
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
FDA UNII
2N81MY12TE
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
NCI_THESAURUS
C61772
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
WIKIPEDIA
FOSFOMYCIN
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
LACTMED
Fosfomycin
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
ECHA (EC/EINECS)
245-463-1
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
EVMPD
SUB07797MIG
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID4048480
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
PUBCHEM
446987
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
SMS_ID
100000086575
Created by admin on Fri Dec 15 16:26:30 GMT 2023 , Edited by admin on Fri Dec 15 16:26:30 GMT 2023
PRIMARY
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TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
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Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Cmax PHARMACOKINETIC ROUTE OF ADMINISTRATION: ORAL

FOOD EFFECT: WITH A HIGH-FAT MEAL

TIME: WITHIN 4 HOURS

DOSE: 3 GRAMS

Volume of Distribution PHARMACOKINETIC
ORAL BIOAVAILABILITY PHARMACOKINETIC FOOD EFFECT: FED

MIC BIOLOGICAL
MIC BIOLOGICAL
MIC BIOLOGICAL
Volume of Distribution PHARMACOKINETIC
ORAL BIOAVAILABILITY PHARMACOKINETIC FOOD EFFECT: FASTING

Cmax PHARMACOKINETIC DOSE: 3 GRAMS

ROUTE OF ADMINISTRATION: ORAL

FOOD EFECT: FASTING

TIME: WITHIN 2 HOURS

Biological Half-life PHARMACOKINETIC