A derivative of nitrofuran, C8H6N4O5, used in the treatment of bacterial infections of the urinary tract.
[NITROFURAN + (hydan)toin, a chemical compound; see diphenylhydantoin.]
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A derivative of nitrofuran, C8H6N4O5, used in the treatment of bacterial infections of the urinary tract.
[NITROFURAN + (hydan)toin, a chemical compound; see diphenylhydantoin.]
Brand names: Furadantin®, Macrobid®, Macrodantin®, Urotoin
Chemical formula:

Nitrofurantoin tablets or capsules
What are nitrofurantoin tablets or capsules?
NITROFURANTOIN (Furadantin®, Macrodantin®, Macrobid®) is an antibiotic. It is used to treat cystitis and other urinary tract infections. Generic nitrofurantoin tablets or capsules are available.
What should I tell my health care provider before I take this medicine?
They need to know if you have any of these conditions:
anemia or other blood disorders
dehydration or fluid or electrolyte problems (problems with the amount of water and salts in your body)
diabetes
glucose-6-phosphate dehydrogenase (G6PD) deficiency
kidney disease
liver disease
lung disease
vitamin B deficiency
other chronic illness
an unusual or allergic reaction to nitrofurantoin, other antibiotics, other medicines, foods, dyes or preservatives
pregnant or trying to get pregnant
breast-feeding
How should I take this medicine?
Take nitrofurantoin tablets or capsules by mouth. Follow the directions on the prescription label. Take with food or milk if nitrofurantoin upsets your stomach. Do not take your medicine more often than directed. Finish the full course of medicine prescribed by your doctor or health care professional, even if you feel better. Take your doses at regular intervals and at the same time each day.
Contact your pediatrician or health care professional regarding the use of this medicine in children. Special care may be needed.
What if I miss a dose?
If you miss a dose, take it as soon as you can. If it is almost time for your next dose, take only that dose. Do not take double doses. You must leave a suitable interval between doses. If you have to take a missed dose make sure there is at least 2 to 4 hours between doses.What drug(s) may interact with nitrofurantoin?
antacids containing magnesium trisilicate
certain antibiotics (such as ciprofloxacin, lomefloxacin, norfloxacin and ofloxacin)
probenecid
sulfinpyrazone
Tell your prescriber or health care professional about all other medicines you are taking, including nonprescription medicines, nutritional supplements, or herbal products. Also tell your prescriber or health care professional if you are a frequent user of drinks with caffeine or alcohol, if you smoke, or if you use illegal drugs. These may affect the way your medicine works. Check with your health care professional before stopping or starting any of your medicines.
What should I watch for while taking nitrofurantoin?
Tell your prescriber or health care professional if your symptoms do not improve in 3 or 4 days.
If you are taking this medicine for a long time, you must visit your prescriber or health care professional for regular checks on your progress.
Drink several glasses of water a day. This will help to reduce possible kidney damage.
If you are diabetic you may get a false-positive result for sugar in your urine. Check with your prescriber or health care professional before you change your diet or the dose of your diabetic medicine.
What side effects may I notice from taking nitrofurantoin?
Side effects that you should report to your prescriber or health care professional as soon as possible:
fever or chills, sore throat
chest pain
cough
difficulty breathing or shortness of breath
dizziness, drowsiness
headache
joint aches or pains
pale skin
redness, blistering, peeling or loosening of the skin, including inside the mouth
skin rash, itching and swelling
tingling, burning, pain, or numbness in hands or feet
unusual bleeding or bruising
unusual weakness or tiredness
vomiting
yellowing of eyes or skin
Side effects that usually do not require medical attention (report to your prescriber or health care professional if they continue or are bothersome):
diarrhea
loss of appetite
nausea
stomach pain
dark yellow or brown urine
Where can I keep my medicine?
Keep out of the reach of children in a container that small children cannot open.
Store at room temperature between 15 and 30 degrees C (59 and 86 degrees F). Protect from light. Throw away any unused medicine after the expiration date.
Last updated: 7/1/2002
Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.
A nitrofuran derivative antibacterial agent used in the treatment of urinary tract infections.
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Nitrofurantoin
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| Systematic (IUPAC) name | |
| 1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dione | |
| Identifiers | |
| CAS number | |
| ATC code | J01 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C8H6N4O5 |
| Mol. mass | 238.16 |
| Pharmacokinetic data | |
| Bioavailability | 40% |
| Metabolism | liver (75%) |
| Half life | 20 minutes |
| Excretion | urine and bile |
| Therapeutic considerations | |
| Pregnancy cat. |
B |
| Legal status |
Rx, PoM |
| Routes | oral |
Nitrofurantoin is an antibiotic. It is usually used in treating urinary tract infection.
Organisms are said to be susceptible to nitrofurantoin if their Minimum inhibitory concentration (MIC) is 32μg/ml or less. The peak blood concentration of nitrofurantoin following an oral dose of nitrofurantoin 100mg, is less than 1 μg/ml and may be undetectable; tissue penetration is negligible; the drug is well concentrated in the urine: 75% of the dose is rapidly metabolised by the liver, but 25% of the dose is excreted in the urine unchanged, reliably achieving levels of 200 μg/ml or more. For this reason, nitrofurantoin cannot be used to treat anything other than simple cystitis.
At the concentrations achieved in urine, nitrofurantoin is bacteriocidal. The mechanism of action of nitrofurantoin is unique and complex. The drug works by damaging bacterial DNA, since its reduced form is highly reactive. This is made possible by the rapid reduction of nitrofurantoin inside the bacterial cell by flavoproteins (nitrofuran reductase) to multiple reactive intermediates that attack ribosomal proteins, DNA,[1] respiration, pyruvate metabolism and other macromolecules within the cell. It is not known which of the actions of nitrofurantoin is primarily responsible for its bacteriocidal acitivity.
Nitrofurantoin and the quinolone antibiotics are mutually antagonistic in vitro. It is not known whether this is of clinical significance, but the combination should be avoided.
Resistance to nitrofurantoin may be chromosomal or plasmid mediated and involves inhibition of nitrofuran reductase.[2] Acquired resistance in E. coli continues to be rare.
Nitrofurantoin and its metabolites are excreted mainly by the kidneys. In renal impairment, the concentration achieved in urine may be subtherapeutic. Nitrofurantoin should not be used in patients with a creatinine clearance of 60 ml/min or less.
The normal adult dose of nitrofurantoin is 50 to 100 mg four times daily for seven days. If a long-acting preparation (e.g., Macrobid®) is used then the dose is 100mg twice daily. The pediatric dose is 3mg/kg/day in four divided doses. Nitrofurantoin should be taken with food, as this improves the absorption of the drug by 45%.
Nitrofurantoin is only clinically proven for use against E. coli or Staph. saprophyticus. It may also have in vitro activity against:
and is used in the treatment of infections caused by these organisms. Only a minority of Enterobacter species and Klebsiella species are sensitive to nitrofurantoin; nitrofurantoin has no activity against
Nitrofurantoin must never be used to treat pyelonephritis,[3] renal abscess, pyeloempyema or any urinary tract infection other than cystitis because of its extremely poor tissue penetration and low blood levels. Urinary catheter infections may be treated with nitrofurantoin if there are no systemic features; the catheter must be changed after 48 hours of antibiotics and treatment is ineffective if the catheter is not replaced or removed.
Nitrofurantoin can cause nausea and vomiting, fever, rash, hypersensitivity pneumonitis. When given for long periods of time, nitrofurantoin can cause progressive pulmonary interstitial fibrosis. All these side effects are much more common in the elderly.
Patients should be informed that nitrofurantoin colours urine a dark orange-brown; this is completely harmless.
Neonates (babies up to the age of one month) have immature enzyme systems in their red blood cells (glutathione instability) and nitrofurantoin must therefore not be used because it can cause haemolytic anaemia. For the same reason, nitrofurantoin should not be given to pregnant women after 38 weeks of pregnancy, or who are about to give birth.
Nitrofurantoin must be taken with food and can cause bleeding in the stomach, vomiting and other gastrointestinal disruptions if these warnings are not adhered to. Nitrofurantoin is contraindicated in patients with glucose-6-phosphate dehydrogenase deficiency because of risk of extravascular hemolysis resulting in anemia.
| Antibacterials for systemic use: others (J01X) | |
|---|---|
| Glycopeptide | Vancomycin - Teicoplanin |
| Polymyxins | Colistin - Polymyxin B |
| Steroid antibacterials | Fusidic acid |
| Imidazole derivatives | Metronidazole - Tinidazole - Ornidazole |
| Nitrofuran derivatives | Nitrofurantoin - Nifurtoinol |
| Other | Fosfomycin - Xibornol - Clofoctol - Spectinomycin - Methenamine - Mandelic acid - Nitroxoline - Linezolid - Daptomycin - Hitachimycin |
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