Fosfomycin

Fosfomycin
Clinical data
Trade names	Monuril, Monurol, Ivozfo, others
Other names	Phosphomycin, phosphonomycin, fosfomycin tromethamine
AHFS/Drugs.com	Monograph
MedlinePlus	a697008
License data	US DailyMed: Fosfomycin;
Routes of; administration	Intravenous, By mouth
ATC code	J01XX01 (WHO) S02AA17 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	30–37% (by mouth, fosfomycin tromethamine); varies with food intake
Protein binding	Nil
Metabolism	Nil
Elimination half-life	5.7 hours (mean)
Excretion	Kidney, unchanged
Identifiers
	IUPAC name [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid;
CAS Number	23155-02-4 ; 78964-85-9 (tromethamine salt);
PubChem CID	446987;
DrugBank	DB00828 ;
ChemSpider	394204 ;
UNII	2N81MY12TE;
KEGG	D04253 ; D00925;
ChEBI	CHEBI:28915 ;
ChEMBL	ChEMBL1757 ;
CompTox Dashboard (EPA)	DTXSID4048480 ;
ECHA InfoCard	100.041.315
Chemical and physical data
Formula	C3H7O4P
Molar mass	138.059 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	94 °C (201 °F)
	SMILES C[C@H]1[C@H](O1)P(=O)(O)O;
	InChI InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1 ; Key:YMDXZJFXQJVXBF-STHAYSLISA-N ;
	(verify)

Fosfomycin, sold under the brand name Monurol among others, is an antibiotic primarily used to treat lower urinary tract infections. It is not indicated for kidney infections. Occasionally it is used for prostate infections. It is generally taken by mouth.

Common side effects include diarrhea, nausea, headache, and vaginal yeast infections. Severe side effects may include anaphylaxis and Clostridioides difficile-associated diarrhea. While use during pregnancy has not been found to be harmful, such use is not recommended. A single dose when breastfeeding appears safe. Fosfomycin works by interfering with the production of the bacterial cell wall.

Fosfomycin was discovered in 1969 and approved for medical use in the United States in 1996 . It is on the World Health Organization's List of Essential Medicines. The World Health Organization classifies fosfomycin as critically important for human medicine. It is available as a generic medication. It was originally produced by certain types of Streptomyces, although it is now made chemically.

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