Structure via PubChem · Public domain (PubChem)
fosfomycin
Sign in to saveAlso known as Phosphonemycin, Fosfomycinum, Phosphonomycin, 1R-cis-(1,2-Epoxypropyl)phosphonic acid, FCM, (1R,2S)-Epoxypropylphosphonic acid, (-)-(1R,2S)-(1,2-Epoxypropyl)phosphonic acid, (2R-cis)-(3-Methyloxiranyl)phosphonic acid
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.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 461113563
- Drug.image
- Fosfomycin.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 125
- Drug.alt
- Structural formula of fosfomycin
- Drug.image2
- Fosfomycin 3D ball.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 150
- Drug.alt2
- Ball-and-stick model of the fosfomycin molecule
- Drug.tradename
- Monuril, Monurol, Ivozfo, others
- Drug.synonyms
- Phosphomycin, phosphonomycin, fosfomycin tromethamine
- Drug.MedlinePlus
- a697008
- Drug.DailyMedID
- Fosfomycin
- Drug.routes_of_administration
- Intravenous, By mouth
- Drug.ATC_prefix
- J01
- Drug.ATC_suffix
- XX01
- Drug.legal_AU
- S4
via Wikipedia infobox
Chemical data
- Formula
- C3H7O4P
- Molecular weight
- 138.06 g/mol
- IUPAC name
- [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
- SMILES
- C[C@H]1[C@H](O1)P(=O)(O)O
- InChIKey
- YMDXZJFXQJVXBF-STHAYSLISA-N
- XLogP
- -1.4
- Polar surface area
- 70.1 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
5,297 papers- Fosfomycin Tromethamine: A Urinary Antibiotic.The Journal of the Association of Physicians of India · 2025
- Fosfomycin: 50 Years of A Great Discovery (1969-2019).Archivos espanoles de urologia · 2022
- Fosfomycin for bacterial prostatitis: a review.International journal of antimicrobial agents · 2020
- [Fosfomycin].Revista espanola de quimioterapia : publicacion oficial de la Sociedad Espanola de Quimioterapia · 2003
- Mobile fosfomycin resistance genes in Enterobacteriaceae-An increasing threat.MicrobiologyOpen · 2020
via PubMed
Wikidata facts
- Mass
- 138.008
Show 5 more facts
- Commons category
- Fosfomycin
- chemical formula
- C₃H₇O₄P
- canonical SMILES
- CC1C(O1)P(=O)(O)O
- isomeric SMILES
- C[C@H]1[C@H](O1)P(=O)(O)O
- World Health Organisation international non-proprietary name
- fosfomycin
Sources (6)
via Wikidata · CC0
~8 min read
Article
10 sectionsContents
- Medical uses
- Bacterial sensitivity
- Resistance
- Side effects
- Mechanism of action
- Immunomodulatory properties
- History
- Biosynthesis
- Synthetic manufacture
- References
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.