Back نيتروفورانتوين Arabic نیتروفورانتوئین AZB Nitrofurantoïna Catalan Nitroffwrantoin Welsh Nitrofurantoin German Νιτροφουραντοΐνη Greek Nitrofurantoína Spanish نیتروفورانتوئین Persian Nitrofurantoiini Finnish Nitrofuran Faeroese

Nitrofurantoin

Nitrofurantoin
Structural formula of nitrofurantoin
Ball-and-stick model of the nitrofurantoin molecule
Clinical data
Trade namesMacrobid, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa682291
License data
Pregnancy
category
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability40%
MetabolismLiver (75%)
Elimination half-life20 minutes
ExcretionKidney and bile duct
Identifiers
  • (E)-1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dione
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.587 Edit this at Wikidata
Chemical and physical data
FormulaC8H6N4O5
Molar mass238.159 g·mol−1
3D model (JSmol)
Melting point270 to 272 °C (518 to 522 °F) (decomp.)
  • O=[N+]([O-])c2oc(/C=N/N1C(=O)NC(=O)C1)cc2
  • InChI=1S/C8H6N4O5/c13-6-4-11(8(14)10-6)9-3-5-1-2-7(17-5)12(15)16/h1-3H,4H2,(H,10,13,14)/b9-3+ checkY
  • Key:NXFQHRVNIOXGAQ-YCRREMRBSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Nitrofurantoin is an antibacterial medication of the nitrofuran class used to treat urinary tract infections, although it is not as effective for kidney infections.[10] It is taken by mouth.[10]

Common side effects include nausea, loss of appetite, diarrhea, and headaches.[10] Rarely numbness, lung problems, or liver problems may occur.[10] While it appears to be generally safe during pregnancy its use is not recommended near time of delivery.[10][2] While it usually works by slowing bacterial growth, it may result in bacterial death at the high concentrations found in urine.[10][failed verification]

Nitrofurantoin was first sold in 1953.[11] It is on the World Health Organization's List of Essential Medicines.[12] It is available as a generic medication.[10] In 2021, it was the 135th most commonly prescribed medication in the United States, with more than 4 million prescriptions.[13][14]

  1. ^ "Nitrofurantoin".
  2. ^ a b "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
  3. ^ Cite error: The named reference Drugs2019Preg was invoked but never defined (see the help page).
  4. ^ "Macrodantin Product Information". TGA eBS. 24 June 2024. Retrieved 24 June 2024.
  5. ^ "Macrodantin Product information". Health Canada. 16 September 1996. Retrieved 24 June 2024.
  6. ^ "Macrobid Product information". Health Canada. 12 August 2021. Retrieved 24 June 2024.
  7. ^ "Macrobid Summary of Product Characteristics (SmPC)". (emc). 14 February 2024. Retrieved 24 June 2024.
  8. ^ "Macrobid - nitrofurantoin monohydrate/macrocrystalline capsule". DailyMed. 30 June 2023. Retrieved 24 June 2024.
  9. ^ https://www.ema.europa.eu/en/documents/psusa/nitrofurantoin-nifurtoinol-list-nationally-authorised-medicinal-products-psusa00002174202102_en.pdf [bare URL PDF]
  10. ^ a b c d e f g "Nitrofurantoin". The American Society of Health-System Pharmacists. Archived from the original on 7 July 2015. Retrieved 1 August 2015.
  11. ^ Blass B (2015). Basic Principles of Drug Discovery and Development. Elsevier. p. 511. ISBN 9780124115255. Archived from the original on 8 September 2017.
  12. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  13. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  14. ^ "Nitrofurantoin - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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