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nitrofurantoin

 
Dictionary: ni·tro·fur·an·to·in   (nī'trō-fyʊ-răn'tō-ĭn) pronunciation
n.

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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Drug Info: Nitrofurantoin
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Brand names: Furadantin®Macrobid®Macrodantin®Urotoin™

Chemical formula:



Nitrofurantoin, Nitrofurantoin, Macrocrystalline Oral capsule

What is this medicine?

NITROFURANTOIN (nye troe fyoor AN toyn) is an antibiotic. It is used to treat urinary tract infections.
 
This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

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
•diabetes
•glucose-6-phosphate dehydrogenase deficiency
•kidney disease
•liver disease
•lung disease
•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 use this medicine?

Take this medicine by mouth with a glass of water. Follow the directions on the prescription label. Take this medicine with food or milk. Take your doses at regular intervals. Do not take your medicine more often than directed. Do not stop taking except on your doctor's advice.

Talk to your pediatrician regarding the use of this medicine in children. While this drug may be prescribed for selected conditions, precautions do apply.

Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.

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 or extra doses. If you take only one dose a day and forget to take it that day, do not take a double dose the next day.

What may interact with this medicine?

•antacids containing magnesium trisilicate
•probenecid
•quinolone antibiotics like ciprofloxacin, lomefloxacin, norfloxacin and ofloxacin
•sulfinpyrazone

This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.

What should I watch for while using this medicine?

Tell your doctor or health care professional if your symptoms do not improve or if you get new symptoms. Drink several glasses of water a day. If you are taking this medicine for a long time, visit your doctor for regular checks on your progress.

If you are diabetic, you may get a false positive result for sugar in your urine with certain brands of urine tests. Check with your doctor.

What side effects may I notice from receiving this medicine?

Side effects that you should report to your doctor or health care professional as soon as possible:
•allergic reactions like skin rash or hives, swelling of the face, lips, or tongue
•chest pain
•cough
•difficulty breathing
•dizziness, drowsiness
•fever or infection
•joint aches or pains
•pale or blue-tinted skin
•redness, blistering, peeling or loosening of the skin, including inside the mouth
•tingling, burning, pain, or numbness in hands or feet
•unusual bleeding or bruising
•unusually weak or tired
•yellowing of eyes or skin

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
•dark urine
•diarrhea
•headache
•loss of appetite
•nausea or vomiting
•temporary hair loss

This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

Where should I keep my medicine?

Keep out of the reach of children.

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.

Veterinary Dictionary: nitrofurantoin
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A nitrofuran derivative antibacterial agent used in the treatment of urinary tract infections.

Wikipedia: Nitrofurantoin
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Nitrofurantoin
Systematic (IUPAC) name
(E)-1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dione
Identifiers
CAS number 67-20-9
ATC code J01XE01
PubChem 5353830
DrugBank APRD00191
ChemSpider 5036498
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, rectal[1]
 Yes check.svgY(what is this?)  (verify)

Nitrofurantoin is an antibiotic which is marketed under the following brand names; Furadantin, Macrobid, Macrodantin, Nitro Macro and Urantoin. It is usually used in treating urinary tract infection. Like many other drugs, it is often used against E Coli.

Contents

Use

Resistance to other antibiotics has led to increased interest in this agent.[2]

It is sometimes described as being appropriate to use in pregnant patients[3] (along with other agents such as sulfisoxazole or cephalexin).[4] This is in contrast to agents such as trimethoprim and ciprofloxacin which may not be appropriate for pregnant women.

Pharmacology

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 100 mg, 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.

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.[5] 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.

Mechanism

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,[6] 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.

Uses

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 100 mg twice daily. The pediatric dose is 3 mg/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,[7] renal abscess, and pyeloempyema because of 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.

Adverse effects

Nitrofurantoin can cause nausea and vomiting, fever, rash, hypersensitivity pneumonitis.[citation needed] It can also cause pulmonary fibrosis.[8] 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 is contraindicated in patients with decreased renal function (CrCl < 60ml/min) due to systemic accumulation and subtherapeutic levels reached in the urinary tract.

Use in food

Residues from the breakdown of nitrofuran veterinary antibiotics, including nitrofurantoin, have been found in chicken in Vietnam, China, Brazil, and Thailand.[9] The European Union banned the use of nitrofurans in food producing animals by classifying it in ANNEX IV (list of pharmacologically active substances for which no maximum residue limits can be fixed) of the Council Regulation 2377/90. The Food and Drug Administration (FDA) of the United States has prohibited furaltadone since February 1985 and withdrew the approval for the other nitrofuran drugs (except some topical uses) in January 1992. The topical use of furazolidone and nitrofurazone was prohibited in 2002. Australia prohibited the use of nitrofurans in food production in 1992. Japan did not allocate MRLs for nitrofurans leading to the implementation of a "zero tolerance or no residue standard". In Thailand, the Ministry of Health issued in 2001 Proclamation No. 231 MRL of veterinary drug in food which did not allocate MRL for nitrofurans. The Ministry of Agriculture and Cooperatives had already prohibited importation and use of furazolidone and nitrofurazone in animal feed in 1999 which was extended to all nitrofurans in 2002. Several metabolites of nitrofurans, such as furazolidone, furaltadone and nitrofurazone cause cancer or genetic damage in rats.[9]

Precautions

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.

Trade names

  • Furadantin (U.S., UK)
  • Macrobid (long acting preparation for twice daily dosing available in U.S., Canada, and UK)
  • Macrodantin (U.S., UK)
  • Furatin (India)
  • Furanit

References

  1. ^ Parrott, E. L.; Matheson Jr, L. E. (1977). "Rectal absorption of nitrofurantoin". Journal of Pharmaceutical Sciences 66 (7): 955–958. doi:10.1002/jps.2600660713. PMID 886458.  edit
  2. ^ Garau J (January 2008). "Other antimicrobials of interest in the era of extended-spectrum beta-lactamases: fosfomycin, nitrofurantoin and tigecycline". Clin. Microbiol. Infect. 14 Suppl 1: 198–202. doi:10.1111/j.1469-0691.2007.01852.x. PMID 18154548. http://www3.interscience.wiley.com/resolve/openurl?genre=article&sid=nlm:pubmed&issn=1198-743X&date=2008&volume=14&issue=&spage=198. 
  3. ^ Lee M, Bozzo P, Einarson A, Koren G (June 2008). "Urinary tract infections in pregnancy". Can Fam Physician 54 (6): 853–4. PMID 18556490. PMC 2426978. http://www.cfp.ca/cgi/pmidlookup?view=long&pmid=18556490. 
  4. ^ "Urinary Tract Infections During Pregnancy - February 1, 2000 - American Academy of Family Physicians". http://www.aafp.org/afp/20000201/713.html. Retrieved 2009-08-04. 
  5. ^ McCalla DR, Kaiser C, Green MHL (1978). "Genetics of nitrofurazone resistance in Escherichia coli". J Bacteriol 133: 10–16. 
  6. ^ Tu Y, McCalla DR (1975). "Effect of activated nitrofurans on DNA,". Biochem Biophys Acta 402: 142–49. 
  7. ^ Richards WA, et al. (1955). "Nitrofurantoin: Clinical and laboratory studies in urinary tract infections". Arch Intern Med 96: 437–50. 
  8. ^ Goemaere NN, Grijm K, van Hal PT, den Bakker MA (2008). "Nitrofurantoin-induced pulmonary fibrosis: a case report". J Med Case Reports 2: 169. doi:10.1186/1752-1947-2-169. PMID 18495029. PMC 2408600. http://www.jmedicalcasereports.com/content/2//169. 
  9. ^ a b FAO: Nitrofuran study


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Dictionary. The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2009. Published by Houghton Mifflin Company. All rights reserved.  Read more
Drug Info. Gold Standard. Copyright © 2008 by Gold Standard. All rights reserved.  Read more
Veterinary Dictionary. Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved.  Read more
Wikipedia. This article is licensed under the Creative Commons Attribution/Share-Alike License. It uses material from the Wikipedia article "Nitrofurantoin" Read more