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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
MOL RATIO 1 MOL RATIO (average)
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
MOL RATIO 1 MOL RATIO (average)
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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Targets

Primary TargetPharmacologyConditionPotency
100.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
MONUROL

Cmax

ValueDoseCo-administeredAnalytePopulation
26.8 μg/mL
3 g single, oral
FOSFOMYCIN TROMETHAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
191 μg × h/mL
3 g single, oral
FOSFOMYCIN TROMETHAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
9.04 h
3 g single, oral
FOSFOMYCIN TROMETHAMINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
unknown, unknown
FOSFOMYCIN TROMETHAMINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as victim

PubMed

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
Record UNII
6226IMZ7MC
Record Status Validated (UNII)
Record Version