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[4]
Drug classAntibiotic
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability~20–94%[11][12][13]
Protein binding60–77% (primarily albumin)[14][13]
Elimination half-life0.33–1.7 hours[12][15][11][14][13]
ExcretionAlmost exclusively urine (4–59% over 3–30 hours; ~20–25% unchanged) and bile[12][15][11][4][14][13]
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
  (verify)

Nitrofurantoin, sold under the brand name Macrobid among others, is an antibacterial medication of the nitrofuran class used to treat urinary tract infections (UTIs), although it is not as effective for kidney infections.[16] It is taken by mouth.[16]

Common side effects include nausea, loss of appetite, diarrhea, and headaches.[16] Rarely numbness, lung problems, or liver problems may occur.[16] While it appears to be generally safe during pregnancy its use is not recommended near time of delivery.[16][2] While it usually works by slowing bacterial growth, it may result in bacterial death at the high concentrations found in urine, provided forced fluid dilution of urine is avoided.[16][failed verification]

Nitrofurantoin was first sold in 1953.[17] It is on the World Health Organization's List of Essential Medicines.[18] It is available as a generic medication.[16] In 2022, it was the 158th most commonly prescribed medication in the United States, with more than 3 million prescriptions.[19][20]

  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. ^ a b https://www.accessdata.fda.gov/drugsatfda_docs/label/2021/020064Orig1s029lbl.pdf
  5. ^ "Macrodantin Product Information". TGA eBS. 24 June 2024. Retrieved 24 June 2024.
  6. ^ "Macrodantin Product information". Health Canada. 16 September 1996. Retrieved 24 June 2024.
  7. ^ "Macrobid Product information". Health Canada. 12 August 2021. Retrieved 24 June 2024.
  8. ^ "Macrobid Summary of Product Characteristics (SmPC)". (emc). 14 February 2024. Retrieved 24 June 2024.
  9. ^ "Macrobid - nitrofurantoin monohydrate/macrocrystalline capsule". DailyMed. 30 June 2023. Retrieved 24 June 2024.
  10. ^ https://www.ema.europa.eu/en/documents/psusa/nitrofurantoin-nifurtoinol-list-nationally-authorised-medicinal-products-psusa00002174202102_en.pdf [bare URL PDF]
  11. ^ a b c Wijma RA, Fransen F, Muller AE, Mouton JW (March 2019). "Optimizing dosing of nitrofurantoin from a PK/PD point of view: What do we need to know?". Drug Resist Updat. 43: 1–9. doi:10.1016/j.drup.2019.03.001. PMID 30947111.
  12. ^ a b c Cunha BA (July 1988). "Nitrofurantoin--current concepts". Urology. 32 (1): 67–71. doi:10.1016/0090-4295(88)90460-8. PMID 3291373.
  13. ^ a b c d Dos Santos C, Dos Santos LS, Franco OL (September 2021). "Fosfomycin and nitrofurantoin: classic antibiotics and perspectives". J Antibiot (Tokyo). 74 (9): 547–558. doi:10.1038/s41429-021-00444-z. PMID 34244614.
  14. ^ a b c Cite error: The named reference Conklin1978 was invoked but never defined (see the help page).
  15. ^ a b Wijma RA, Huttner A, Koch BC, Mouton JW, Muller AE (November 2018). "Review of the pharmacokinetic properties of nitrofurantoin and nitroxoline". Journal of Antimicrobial Chemotherapy. 73 (11): 2916–2926. doi:10.1093/jac/dky255. PMID 30184207.
  16. ^ 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.
  17. ^ Blass B (2015). Basic Principles of Drug Discovery and Development. Elsevier. p. 511. ISBN 9780124115255. Archived from the original on 8 September 2017.
  18. ^ 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.
  19. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  20. ^ "Nitrofurantoin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.