Nitrofurantoin

Nitrofurantoin

Clinical data
Trade names	Macrobid, Macrodantin and others
AHFS/Drugs.com	Monograph
MedlinePlus	a682291
Pregnancy category	AU: A US: B (No risk in non-human studies)
Routes of administration	by mouth
ATC code	J01XE01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	40%
Metabolism	liver (75%)
Biological half-life	20 minutes
Excretion	urine and bile
Identifiers
IUPAC name (E)-1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dione
CAS Number	67-20-9 Y
PubChem (CID)	6604200
DrugBank	DB00698 Y
ChemSpider	5036498 Y
UNII	927AH8112L Y
KEGG	D00439 Y
ChEBI	CHEBI:71415 N
ChEMBL	CHEMBL572 Y
ECHA InfoCard	100.000.587
Chemical and physical data
Formula	C8H6N4O5
Molar mass	238.16
3D model (Jmol)	Interactive image
Melting point	270 to 272 °C (518 to 522 °F) (decomp.)
SMILES O=[N+]([O-])c2oc(/C=N/N1C(=O)NC(=O)C1)cc2
InChI 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+ Y Key:NXFQHRVNIOXGAQ-YCRREMRBSA-N Y
NY (what is this?)

Nitrofurantoin, sold under the trade name Macrobid among others, is an antibiotic used to treat bladder infections. It is not effective for kidney infections. 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. It should not be used in people with kidney problems. While it appears to be generally safe during pregnancy it should not be used near delivery. It works by slowing growth rather than killing bacteria.

Nitrofurantoin was first sold in 1953. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world is between 0.005 and 0.46 USD a dose. In the United States it is about 60 USD for 10 days of treatment.

Current uses include the treatment of uncomplicated urinary tract infections (UTIs) and prophylaxis against UTIs in people prone to recurrent UTIs.

Increasing bacterial antibiotic resistance to other commonly used agents, such as fluoroquinolones and trimethoprim/sulfamethoxazole, has led to increased interest in using nitrofurantoin. Several trials comparing nitrofurantoin to other commonly used agents have shown this drug results in similar cure rates for uncomplicated UTIs. The efficacy of nitrofurantoin in treating UTIs combined with a low rate of bacterial resistance to this agent makes it one of the first-line agents for treating uncomplicated UTIs as recommended by the Infectious Diseases Society of America and the European Society for Microbiology and Infectious Diseases.

Nitrofurantoin is not recommended for the treatment of pyelonephritis,prostatitis and intra-abdominal abscess, because of extremely poor tissue penetration and low blood levels.