Structure via PubChem · Public domain (PubChem)
nitrofurantoin
Sign in to saveAlso known as N-(5-Nitrofurfurylidene)-1-aminohydantoin, SID11112186, 5-Nitrofurantoin
Nitrofurantoin, sold under the brand name Macrobid among others, is an antibacterial medication of the nitrofuran class. It is used primarily to treat lower urinary tract infections (UTIs) but it is also used in bladder infections. It is not indicated for kidney infections nor is it as effective for them. It is taken by mouth.
Key facts
- Drug.Verifiedfields
- verified
- Drug.Watchedfields
- verified
- Drug.verifiedrevid
- 462261865
- Drug.image
- Nitrofurantoin.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250px
- Drug.alt
- Structural formula of nitrofurantoin
- Drug.image2
- Nitrofurantoin-from-xtal-3D-bs-17.png
- Drug.image_class2
- bg-transparent
- Drug.alt2
- Ball-and-stick model of the nitrofurantoin molecule
- Drug.tradename
- Macrobid, others
- Drug.MedlinePlus
- a682291
- Drug.DailyMedID
- Nitrofurantoin
- Drug.pregnancy_AU
- A
- Drug.routes_of_administration
- By mouth
- Drug.class
- Antibiotic
- Drug.ATC_prefix
- J01
- Drug.ATC_suffix
- XE01
via Wikipedia infobox
Chemical data
- Formula
- C8H6N4O5
- Molecular weight
- 238.16 g/mol
- IUPAC name
- 1-[(E)-(5-nitrofuran-2-yl)methylideneamino]imidazolidine-2,4-dione
- SMILES
- C1C(=O)NC(=O)N1/N=C/C2=CC=C(O2)[N+](=O)[O-]
- InChIKey
- NXFQHRVNIOXGAQ-YCRREMRBSA-N
- XLogP
- -0.5
- Polar surface area
- 121 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
6,079 papers- Nitrofurantoin.IARC monographs on the evaluation of carcinogenic risks to humans · 1990
- Nitrofurantoin: an update.Obstetrical & gynecological survey · 1989
- Nitrofurantoin--current concepts.Urology · 1988
- Unlocking Nitrofurantoin: Understanding Molecular Mechanisms of Action and Resistance in Enterobacterales.Medical principles and practice : international journal of the Kuwait University, Health Science Centre · 2025
- Nitrofurantoin-induced hepatotoxicity: a rare yet serious complication.Southern medical journal · 2014
via PubMed
~9 min read
Encyclopedic overview
20 sectionsContents
- Medical uses
- Urinary tract infections
- Other bacterial infections
- Antibacterial activity
- Special populations
- Pregnancy
- Contraindications
- Adverse effects
- Lung toxicity
- Liver toxicity
- Neuropathy
- Gut microflora
- Interactions
- Pharmacology
- Mechanism of action
- History
- Society and culture
- Brand names
- Animal feed
- References
Nitrofurantoin, sold under the brand name Macrobid among others, is an antibacterial medication of the nitrofuran class. It is used primarily to treat lower urinary tract infections (UTIs) but it is also used in bladder infections. It is not indicated for kidney infections nor is it as effective for them. It is taken by mouth.
Common side effects include nausea, loss of appetite, diarrhea, and headaches. Rarely numbness, lung problems, or liver problems may occur. While it appears to be generally safe during pregnancy its use is not recommended near time of delivery. 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.
Excerpted from Wikipedia’s “nitrofurantoin” article, available under the CC BY-SA 4.0 licence.