Nitrofurazone

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
ATC code
Legal status
Legal status
  • US: Discontinued
Pharmacokinetic data
Elimination half-life5 hours
Identifiers
  • (2E)-2-[(5-Nitro-2-furyl)methylene]hydrazine
    carboxamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.403 Edit this at Wikidata
Chemical and physical data
FormulaC6H6N4O4
Molar mass198.138 g·mol−1
3D model (JSmol)
  • O=[N+]([O-])c1oc(/C=N/NC(=O)N)cc1
  • InChI=1S/C6H6N4O4/c7-6(11)9-8-3-4-1-2-5(14-4)10(12)13/h1-3H,(H3,7,9,11)/b8-3+ checkY
  • Key:IAIWVQXQOWNYOU-FPYGCLRLSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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]

  1. ^ a b "Nitrofural". www.drugbank.ca. Retrieved 2018-03-14.
  2. ^ a b "Nitrofurazone (Topical route)". Drugs.com.
  3. ^ "Nitrofurazone". Pubchem. U.S. National Library of Medicine. Retrieved 2018-03-14.
  4. ^ "nitrofurazone". www.glowm.com. Retrieved 2018-03-14.
  5. ^ a b Perez S (26 May 2010). "Nitrofuran Analyses". Adpen Laboratories. Retrieved 14 March 2018.
  6. ^ "Nitrofurazone". Office of Environmental Health Hazard Assessment. 2015-03-22. Retrieved 2018-03-14.
  7. ^ National Toxicology Program (June 1988). "NTP Toxicology and Carcinogenesis Studies of Nitrofurazone in F344/N Rats and B6C3F1 Mice (Feed Studies)" (PDF). National Toxicology Program Technical Report Series. 337. NIH Publication No. 88-2593. National Institute of Health: 1–186.
  8. ^ Vass M, Hruska K, Franek M (2008). "Nitrofuran antibiotics: a review on the application, prohibition and residual analysis". Veterinarni Medicina. 53 (9): 469–500. doi:10.17221/1979-VETMED.
  9. ^ "Nitrofurazone Ointment for Animal Use - Drugs.com". Drugs.com. Retrieved 2018-03-14.