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

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
Structure of FOSFOMYCIN (R)-1-PHENETHYLAMINE MONOHYDRATE

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

HIDE SMILES / InChI
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 H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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

Description

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.

CNS Activity

Originator

Approval Year

1996
225
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 100.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/050717s009lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/050717Orig1s000rev.pdf
Page: MON-US-02
unhealthy, 32
n = 426
Health Status: unhealthy
Condition: Infection
Age Group: 32
Sex: M+F
Population Size: 426
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/050717Orig1s000rev.pdf
Page: MON-US-02
Disc. AE: Diarrhea, Erythema...
AEs leading to
discontinuation/dose reduction:
Diarrhea
Erythema
Vomiting
Rash
Dry mouth
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/050717Orig1s000rev.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/050717Orig1s000rev.pdf
Page: MON-US-02
unhealthy, 32
n = 426
Health Status: unhealthy
Condition: Infection
Age Group: 32
Sex: M+F
Population Size: 426
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/050717Orig1s000rev.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/050717Orig1s000rev.pdf
Page: MON-US-02
unhealthy, 32
n = 426
Health Status: unhealthy
Condition: Infection
Age Group: 32
Sex: M+F
Population Size: 426
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/050717Orig1s000rev.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/050717Orig1s000rev.pdf
Page: MON-US-02
unhealthy, 32
n = 426
Health Status: unhealthy
Condition: Infection
Age Group: 32
Sex: M+F
Population Size: 426
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/050717Orig1s000rev.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/050717Orig1s000rev.pdf
Page: MON-US-02
unhealthy, 32
n = 426
Health Status: unhealthy
Condition: Infection
Age Group: 32
Sex: M+F
Population Size: 426
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/050717Orig1s000rev.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/050717Orig1s000rev.pdf
Page: MON-US-02
unhealthy, 32
n = 426
Health Status: unhealthy
Condition: Infection
Age Group: 32
Sex: M+F
Population Size: 426
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/nda/96/050717Orig1s000rev.pdf
Page: MON-US-02
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP
111
CYP
270

UGT
192
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP
147
 no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
270
 no
UGT
192
 no
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:28915
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28915
ZINC
ZINC000001530427
http://zinc15.docking.org/substances/ZINC000001530427
PubMed

PubMed

TitleDatePubMed
Effects of fosfomycin and imipenem-cilastatin on the nephrotoxicity of vancomycin and cisplatin in rats.
1999 Feb
[A case report of urinary tract infection and meningitis caused by methicillin-resistant Staphylococcus aureus (MRSA) after transurethral resection of the prostate].
1999 Mar
Acute, recurrent fosfomycin-induced liver toxicity in an adult patient with cystic fibrosis.
2001
[Activity of bicozamycin against Escherichia coli O157:H7 producing Vero toxin].
2001
FosB, a cysteine-dependent fosfomycin resistance protein under the control of sigma(W), an extracytoplasmic-function sigma factor in Bacillus subtilis.
2001 Apr
Thermodynamic characterization of ligand-induced conformational changes in UDP-N-acetylglucosamine enolpyruvyl transferase.
2001 Aug 21
Campylobacter, Salmonella, Shigella and Escherichia coli in live and dressed poultry from metropolitan accra.
2001 Dec 4
[Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine].
2001 Feb
[Correlation between sensitivity to fosfomycin and the presence of penicillinase PSE-1 in Pseudomonas aeruginosa].
2001 Feb
The effect of fosfomycin on neutrophil function.
2001 Feb
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
Two cases of severe bronchopneumonia due to influenza A (H3N2) virus: detection of influenza virus gene using reverse transcription polymerase chain reaction.
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
Thermal stability of disodium and calcium phosphomycin and the effects of the excipients evaluated by thermal analysis.
2001 Mar
Diaryl ester prodrugs of FR900098 with improved in vivo antimalarial activity.
2001 Mar 26
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
[Urinary infection caused by Oligella urethralis].
2001 Nov 30
Time-kill evaluation of antimicrobial regimens against clinical isolates of penicillin-resistant Streptococcus pneumoniae.
2001 Oct
Biosynthetic pathway of insect juvenile hormone III in cell suspension cultures of the sedge Cyperus iria.
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
The role of murMN operon in penicillin resistance and antibiotic tolerance of Streptococcus pneumoniae.
2001 Winter
In vitro susceptibility of vancomycin-resistant enterococci (VRE) to fosfomycin.
2002 Apr
Mevalonate and nonmevalonate pathways for the biosynthesis of isoprene units.
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
Biofilm testing of Staphylococcus epidermidis clinical isolates: low performance of vancomycin in relation to other antibiotics.
2002 Dec
Fosmidomycin for malaria.
2002 Dec 14
Pseudo-septic meningeal reaction after intradural glucocorticoid therapy for sciatica.
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
[Indicators for early diagnosis of enterohemorrhagic Escherichia coli infection and methods for final diagnosis].
2002 Jun
A pathway-specific cell based screening system to detect bacterial cell wall inhibitors.
2002 Mar
[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
On-line analysis of the (13)CO(2) labeling of leaf isoprene suggests multiple subcellular origins of isoprene precursors.
2002 Oct
[Staphylococcus aureus meningitis with intermediate sensitivity to glycopeptides. Therapeutic indications].
2003 Feb 8
Patents

Patents

EP1762573A1
8
US4937367
8
US8604078
8
WO2015070131A1
8

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
In Vitro Use Guide
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 Sat Dec 16 07:42:55 GMT 2023
Edited
by admin
on Sat Dec 16 07:42:55 GMT 2023
Record UNII
6226IMZ7MC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FOSFOMYCIN (R)-1-PHENETHYLAMINE MONOHYDRATE
Common Name English
BENZENEMETHANAMINE, .ALPHA.-METHYL-, (R)-, (2R-CIS)-(3-METHYLOXIRANYL)PHOSPHONATE (1:1), MONOHYDRATE
Systematic Name English
FOSFOMYCIN PHENETHYLAMMONIUM MONOHYDRATE
Common Name English
PHOSPHONIC ACID, (3-METHYLOXIRANYL)-, (2R-CIS)-, COMPD. WITH (R)-.ALPHA.-METHYLBENZENEMETHANAMINE (1:1), MONOHYDRATE
Systematic Name English
Code System Code Type Description
PUBCHEM
91617671
Created by admin on Sat Dec 16 07:42:56 GMT 2023 , Edited by admin on Sat Dec 16 07:42:56 GMT 2023
PRIMARY
CAS
65794-75-4
Created by admin on Sat Dec 16 07:42:56 GMT 2023 , Edited by admin on Sat Dec 16 07:42:56 GMT 2023
PRIMARY
FDA UNII
6226IMZ7MC
Created by admin on Sat Dec 16 07:42:56 GMT 2023 , Edited by admin on Sat Dec 16 07:42:56 GMT 2023
PRIMARY
Related Record Type Details
Structure of FOSFOMYCIN (R)-1-PHENETHYLAMINE
ANHYDROUS->SOLVATE
Related Record Type Details
Structure of FOSFOMYCIN
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966