Fosfomycin

Not to be confused with Fosmidomycin.

Fosfomycin
Structural formula of fosfomycin
Ball-and-stick model of the fosfomycin molecule
Clinical data
Trade namesMonuril, Monurol, Ivozfo, others
Other namesPhosphomycin, phosphonomycin, fosfomycin tromethamine
AHFS/Drugs.comMonograph
MedlinePlusa697008
License data
Routes of
administration		Intravenous, By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability30–37% (by mouth, fosfomycin tromethamine); varies with food intake
Protein bindingNil
MetabolismNil
Elimination half-life5.7 hours (mean)
ExcretionKidney, unchanged
Identifiers
  • [(2R,3S)-3-methyloxiran-2-yl]phosphonic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.041.315 Edit this at Wikidata
Chemical and physical data
FormulaC3H7O4P
Molar mass138.059 g·mol−1
3D model (JSmol)
Melting point94 °C (201 °F)
  • C[C@H]1[C@H](O1)P(=O)(O)O
  • InChI=1S/C3H7O4P/c1-2-3(7-2)8(4,5)6/h2-3H,1H3,(H2,4,5,6)/t2-,3+/m0/s1 checkY
  • Key:YMDXZJFXQJVXBF-STHAYSLISA-N checkY
  (verify)

Fosfomycin, sold under the brand name Monurol among others, is an antibiotic primarily used to treat lower urinary tract infections.[8] It is not indicated for kidney infections.[8] Occasionally it is used for prostate infections.[8] It is generally taken by mouth.[8]

Common side effects include diarrhea, nausea, headache, and vaginal yeast infections.[8] Severe side effects may include anaphylaxis and Clostridioides difficile-associated diarrhea.[8] While use during pregnancy has not been found to be harmful, such use is not recommended.[9] A single dose when breastfeeding appears safe.[9] Fosfomycin works by interfering with the production of the bacterial cell wall.[8]

Fosfomycin was discovered in 1969 and approved for medical use in the United States in 1996 [globalize][8][10] It is on the World Health Organization's List of Essential Medicines.[11] The World Health Organization classifies fosfomycin as critically important for human medicine.[12] It is available as a generic medication.[13] It was originally produced by certain types of Streptomyces, although it is now made chemically.[10]

  1. ^ "Prescription medicines: registration of new chemical entities in Australia, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 10 April 2023. Retrieved 9 April 2023.
  2. ^ "Prescription medicines and biologicals: TGA annual summary 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 31 March 2024.
  3. ^ https://www.tga.gov.au/resources/prescription-medicines-registrations/cipfosin-cipla-fosfomycin-cipla-australia-pty-ltd
  4. ^ "Regulatory Decision Summary - Ivozfo". Health Canada. 23 October 2014. Archived from the original on 7 June 2022. Retrieved 7 June 2022.
  5. ^ "Monuril 3g granules for oral solution - Summary of Product Characteristics (SmPC)". (emc). 1 June 2021. Archived from the original on 8 March 2022. Retrieved 7 June 2022.
  6. ^ "Fomicyt 40 mg/mL powder for solution for infusion - Summary of Product Characteristics (SmPC)". (emc). 11 February 2021. Archived from the original on 7 June 2022. Retrieved 7 June 2022.
  7. ^ "Monurol- fosfomycin tromethamine powder". DailyMed. 24 October 2019. Archived from the original on 7 June 2022. Retrieved 7 June 2022.
  8. ^ a b c d e f g h "Fosfomycin Tromethamine Monograph for Professionals". Drugs.com. Archived from the original on 29 October 2019. Retrieved 29 October 2019.
  9. ^ a b "Fosfomycin (Monurol) Use During Pregnancy". Drugs.com. Archived from the original on 29 October 2019. Retrieved 29 October 2019.
  10. ^ a b Finch RG, Greenwood D, Whitley RJ, Norrby SR (2010). Antibiotic and Chemotherapy E-Book. Elsevier Health Sciences. p. 259. ISBN 9780702047657.
  11. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  12. ^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528.
  13. ^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 560–561. ISBN 9780857113382.