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Substance Name: Nitrofurazone [USP:INN:BAN]
RN: 59-87-0
UNII: X8XI70B5Z6
InChIKey: IAIWVQXQOWNYOU-FPYGCLRLSA-N

Note

  • A topical anti-infective agent effective against gram-negative and gram-positive bacteria. It is used for superficial WOUNDS AND INJURIES and skin infections. Nitrofurazone has also been administered orally in the treatment of TRYPANOSOMIASIS.

Molecular Formula

  • C6-H6-N4-O4

Molecular Weight

  • 198.1374
 

Classification Codes

Classification Codes

  • Agricultural Chemical
  • Anti-Infective Agents
  • Anti-Infective, Topical
  • Drug / Therapeutic Agent
  • Germicide, Bactericide, Disinfectant
  • Mutation Data
  • Reproductive Effect
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Results Name

  • Nitrofurazone [USP:INN:BAN]

Name of Substance

  • Nitrofural [INN]
  • Nitrofurazone
  • Nitrofurazone [USP:INN:BAN]

MeSH Heading

  • Nitrofurazone

Synonyms

  • (5-Nitro-2-furfurylidenamino)urea
  • 1-(5-Nitro-2-furfurylidene)semicarbazide
  • 2((5-Nitro-2-furanyl)methylene)hydrazinecarboxamide
  • 2-Furaldehyde, 5-nitro-, semicarbazone
  • 2-Furancarboxaldehyde, 5-nitro-, semicarbazone
  • 5-17-09-00335 (Beilstein Handbook Reference)
  • 5-Nitro-2-furaldehyde semicarbazone
  • 5-Nitro-2-furancarboxaldehyde semicarbazone
  • 5-Nitro-2-furfural semicarbazone
  • 5-Nitro-2-furfuraldehyde semicarbazone
  • 5-Nitrofuraldehyde semicarbazide
  • 5-Nitrofuran-2-aldehyde semicarbazone
  • 5-Nitrofurazone
  • 5-Nitrofurfural semicarbazone
  • 6-Nitrofuraldehyde semicarbazide
  • Actin-N
  • Acutol
  • AI3-17333
  • Aldomycin
  • Alfucin
  • Amifur
  • Babrocid
  • Becafurazone
  • Biofuracina
  • Biofurea
  • BRN 0086403
  • CCRIS 1195
  • Chemofuran
  • Chixin
  • Cocafurin
  • Coxistat
  • Dermofural
  • Dynazone
  • EINECS 200-443-1
  • Eldezol
  • Eldezol F-6
  • Fedacin
  • Flavazone
  • Fracine
  • Fura-septin
  • Furacilin
  • Furacilinum
  • Furacillin
  • Furacin
  • Furacin-E
  • Furacin-HC
  • Furacine
  • Furacinetten
  • Furacoccid
  • Furacort
  • Furacycline
  • Furaderm
  • Furagent
  • Furaldon
  • Furalone
  • Furametral
  • Furan-ofteno
  • Furaplast
  • Furaseptyl
  • Furaskin
  • Furatsilin
  • Furaziline
  • Furazin
  • Furazina
  • Furazol W
  • Furazone
  • Furazyme
  • Furesol
  • Furfurin
  • Furosem
  • Fuvacillin
  • Hemofuran
  • HSDB 3136
  • Hydrazinecarboxamide, 2-((5-nitro-2-furanyl)methylene)-
  • Ibiofural
  • Mammex
  • Mastofuran
  • Monafuracin
  • Monafuracis
  • Monofuracin
  • NCI-C56064
  • Nefco
  • NF-7
  • NFS
  • NFZ
  • Nifucin
  • Nifurid
  • Nifuzon
  • Nitrofural
  • Nitrofuraldehyde semicarbazone
  • Nitrofuralum
  • Nitrofuralum [INN-Latin]
  • Nitrofuran
  • Nitrofuran (bactericide)
  • Nitrofurane
  • Nitrofurazan
  • Nitrofurazone
  • Nitrofurazonum
  • Nitrofurol
  • Nitrozone
  • NSC 1602
  • NSC 2100
  • NSC-2100
  • Otofural
  • Otofuran
  • Rivafurazon
  • Rivopon-5
  • Sanfuran
  • Semikarbazon 5-nitrofurfuralu
  • Semikarbazon 5-nitrofurfuralu [Polish]
  • Spray-dermis
  • Spray-foral
  • U-6421
  • UNII-X8XI70B5Z6
  • USAF EA-4
  • Vabrocid
  • Vadrocid
  • Veterinary nitrofurazone
  • Yatrocin

Systematic Names

  • 2-Furaldehyde, 5-nitro-, semicarbazone
  • Hydrazinecarboxamide, 2-((5-nitro-2-furanyl)methylene)-
  • Nitrofural
  • Nitrofurazone

Superlist Names

  • Nitrofural
  • Nitrofurazone

Registry Numbers

CAS Registry Number

  • 59-87-0

FDA UNII

  • X8XI70B5Z6

Other Registry Numbers

  • 60051-85-6
  • 8027-71-2

System Generated Number

  • 0000059870

Structure Descriptors

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+

InChIKey

IAIWVQXQOWNYOU-FPYGCLRLSA-N

Smiles

c1(oc(cc1)/C=N/NC(=O)N)[N+](=O)[O-]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 96mg/kg (96mg/kg)   Journal of Medicinal Chemistry. Vol. 10, Pg. 530, 1967.
mouse LD50 oral 249mg/kg (249mg/kg)   Transactions of the Royal Society of Tropical Medicine and Hygiene. Vol. 74, Pg. 43, 1980.
mouse LD50 subcutaneous 753mg/kg (753mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 102, Pg. 185, 1951.
rat LD50 oral 590mg/kg (590mg/kg)   JAMA, Journal of the American Medical Association. Vol. 133, Pg. 299, 1947.
rat LD50 subcutaneous 3gm/kg (3000mg/kg)   JAMA, Journal of the American Medical Association. Vol. 133, Pg. 299, 1947.
rat LDLo intraperitoneal 150mg/kg (150mg/kg)   Biochemical Pharmacology. Vol. 13, Pg. 285, 1964.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 238 dec deg C   EXP
pKa Dissociation Constant 10 (none)   EXP
log P (octanol-water) 0.23 (none)   EXP
Water Solubility 210 mg/L 25 EXP
Vapor Pressure 4.31E-06 mm Hg 25 EST
Henry's Law Constant 3.10E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.59E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.