Chemistry:Nitrofurazone

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Short description: Chemical compound
Nitrofurazone
Skeletal formula of nitrofural
Space-filling model of the nitrofural molecule
Clinical data
Trade namesAldomycin, Amifur, Chemfuran, Coxistat, Furacin, Furan-2, Furacinetten, Furaplast, Furazol W, Furesol Furracoccid, Mammex, Nefco, Nifuzon, Nitrofural, Vabrocid
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy
category
  • US: C (Risk not ruled out)
ATC code
Legal status
Legal status
  • US: Discontinued
Pharmacokinetic data
Elimination half-life5 hours
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC6H6N4O4
Molar mass198.138 g·mol−1
3D model (JSmol)
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Nitrofurazone (INN, trade name Furacin) is an antimicrobial organic compound belonging to the nitrofuran class.[1] It is most commonly used as a topical antibiotic ointment.[2] It is effective against gram-positive bacteria, gram-negative bacteria, and can be used in the treatment of trypanosomiasis.[1][3][4] Its use in medicine has become less frequent, as safer and more effective products have become available.[5] Nitrofurazone is listed under California Prop 65, and has demonstrated clear evidence to be mutagenic and carcinogenic during animal studies, and has been discontinued for human use in the USA.[2][5][6][7] The substance is pale yellow and crystalline. It was once widely used as an antibiotic for livestock.[8][9]

Medical uses

Drugstore-made ~400 mL aqueous solution of Furacilin (Russian: Фурацилин, nitrofural), 1 : 5000 (0.2 mg/mL or 0.02%), ready for topical use.

Human use

Nitrofurazone was previously available as a prescription in the U.S., and was indicated as a topical solution, topical cream, or topical ointment for the treatment of bacterial skin infections, wounds, burns, and ulcers.[2] It was also used as a prophylactic measure to prevent infection that could potentially result in skin graft rejection.[1][10] Nitrofurazone is still very popular as a topical solution for the treatment of tonsillitis in Russia.[citation needed]

Animal use

Nitrofurazone is indicated for topical use in dogs, cats, and horses, for the treatment or prophylactic treatment of superficial bacterial infections, burns, and cutaneous ulcers.[9] Preparations for treating infections, such as fin rot, in ornamental fish are also still commercially available.[11][12] The use of nitrofurazone, or related compounds, in animals raised for human consumption has been strictly banned.[11][13]

Pharmacokinetics

The mechanism of action is not fully understood, but nitrofurazone's antimicrobial properties are suspected to be due to the interference of DNA synthesis in the microorganism by inhibiting certain enzymes that are involved with glycolysis.[1][5] Other enzymes this may affect include, pyruvate dehydrogenase, citrate synthetase, malate dehydrogenase, glutathione reductase, and pyruvate decarboxylase.[1]

The metabolism of topically applied nitrofurazone is thought to be by 5-nitro reduction and cleavage of the -CH=N- linkage to generate a reactive species which can covalently bond to cellular macromolecules, none of the end products are thought to be antimicrobial.[1][14]

Adverse effects

Adverse effects for topical use are generally mild and include, erythema, pruritus, dermatitis, rash, edema or inflammation.[1][2]

Contraindications

People with chronic kidney disease and large total body surface area (TBSA) burns should not use nitrofurazone, as topical preparations commonly contain polyethylene glycol, which is readily absorbed through the skin. Rapid absorption of the medication induces increased serum osmolalities and anion gap, leading to death.[15] Symptoms are similar to ethylene glycol poisoning, in that increased serum calcium levels occur concurrently with decreased ionized calcium.[15]

Nitrofurans have been found in honey, meat and seafood. In people who have glucose-6-phosphate dehydrogenase deficiency (G-6-PD deficiency), ingestion of fish, poultry, or other foodstuff that has been treated with nitrofurans, will likely suffer from hemolysis of red blood cells as a result of eating the contaminated food.[5]

Toxicities

Nitrofurazone is suspected to be a human carcinogen and is included in California's list of toxic chemicals as defined by Proposition 65.[6][7][16] Studies demonstrate that nitrofurazone induces mammary tumors (fibroadenoma and adenocarcinoma) in rats and ovarian tumors in mice.[7] In addition, animal studies demonstrated an increased incidence in convulsive seizures, ovarian atrophy, testicular degeneration, and degeneration of articular cartilage.[7][17] Proper personal protective equipment should be utilized when handling nitrofurazone.[9]

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "Nitrofural". https://www.drugbank.ca/drugs/DB00336. 
  2. ↑ 2.0 2.1 2.2 2.3 "Nitrofurazone (Topical route)". Drugs.com. https://www.drugs.com/cons/nitrofurazone-topical.html. 
  3. ↑ "Nitrofurazone". Pubchem. U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/nitrofurazone#section=Top. 
  4. ↑ "nitrofurazone". https://www.glowm.com/resources/glowm/cd/pages/drugs/n026.html. 
  5. ↑ 5.0 5.1 5.2 5.3 Perez, Steven (26 May 2010). "Nitrofuran Analyses". http://adpen.com/2010/05/nitrofurans/. 
  6. ↑ 6.0 6.1 "Nitrofurazone". Office of Environmental Health Hazard Assessment. 2015-03-22. https://oehha.ca.gov/chemicals/nitrofurazone. 
  7. ↑ 7.0 7.1 7.2 7.3 National Toxicology Program (June 1988). NIH Publication No. 88-2593. "NTP Toxicology and Carcinogenesis Studies of Nitrofurazone in F344/N Rats and B6C3F1 Mice (Feed Studies)". National Toxicology Program Technical Report Series. 337 (National Institute of Health): 1–186. https://ntp.niehs.nih.gov/ntp/htdocs/lt_rpts/tr337.pdf. 
  8. ↑ "Nitrofuran antibiotics: a review on the application, prohibition and residual analysis". Veterinarni Medicina 53 (9): 469–500. 2008. doi:10.17221/1979-VETMED. 
  9. ↑ 9.0 9.1 9.2 "Nitrofurazone Ointment for Animal Use - Drugs.com" (in en-US). Drugs.com. https://www.drugs.com/vet/nitrofurazone-ointment.html. 
  10. ↑ "Aldomycin". Minimally Invasive Neurosurgery Clinic. http://www.minclinic.ru/drugs/drugs_eng/A/Aldomycin.html. 
  11. ↑ 11.0 11.1 Yanong, Roy P. E. (2017-01-05). "Use of Antibiotics in Ornamental Fish Aquaculture". http://edis.ifas.ufl.edu/fa084. 
  12. ↑ Giovanetti, Thomas A. (1991). Discus Fish. Barron's Educational Series. ISBN 9780812046694. https://books.google.com/books?id=GykB84HU6LoC&pg=PA71. 
  13. ↑ Center for Food Safety and Applied Nutrition, U.S. Department of Health and Human Services (April 2011). "Fish and Fishery Products Hazards and Controls Guidance" (in en). Food and Drug Administration. pp. 183–208. https://www.fda.gov/downloads/Food/GuidanceRegulation/UCM251970.pdf. 
  14. ↑ Residues of Some Veterinary Drugs in Animals and Foods: Monographs Prepared by the Fortieth Meeting of the Joint FAO/WHO Expert Committee on Food Additives, Geneva, 9-18 June 1992. Food and Agriculture Organization of the United Nations. 1993. ISBN 9789251032886. https://books.google.com/books?id=2IepBlgVqZcC&pg=PA107. 
  15. ↑ 15.0 15.1 Thermal Burns: Overview, Pathophysiology, Quantifying Burn Severity. 2017-12-29. https://emedicine.medscape.com/article/1278244-overview#a7. 
  16. ↑ "Activation of nitrofurazone by azoreductases: multiple activities in one enzyme" (in En). Scientific Reports 1 (1): 63. 2011-08-12. doi:10.1038/srep00063. PMID 22355582. Bibcode: 2011NatSR...1E..63R. 
  17. ↑ "Abstract for TR-337" (in en). https://ntp.niehs.nih.gov/results/pubs/longterm/reports/longterm/tr300399/abstracts/tr337/index.html. 



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