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Substance Name: Nifurtimox [INN:BAN]
RN: 23256-30-6
UNII: M84I3K7C2O
InChIKey: ARFHIAQFJWUCFH-IZZDOVSWSA-N

Note

  • A nitrofuran thiazine that has been used against TRYPANOSOMIASIS.

Molecular Formula

  • C10-H13-N3-O5-S

Molecular Weight

  • 287.2947
 

Classification Codes

  • Anti-Infective Agents
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Drug / Therapeutic Agent
  • Mutation Data
  • Reproductive Effect
  • Trypanocidal Agents
  • Tumor Data

Names and Synonyms

Name of Substance

  • Nifurtimox
  • Nifurtimox [INN:BAN]

MeSH Heading

  • Nifurtimox

Synonyms

  • 1-((5-Nitrofurfurylidene)amino)-2-methyltetrahydro-1,4-thiazine-4,4-dioxide
  • 3-Methyl-4-(5'-nitrofurylidene-amino)-tetrahydro-4H-1,4-thiazine-1,1-dioxide
  • 4-((5-Nitrofurfurylidene)amino)-3-methylthiomorpholine 1,1-dioxide
  • 4-((5-Nitrofurfurylidene)amino)-3-methylthiomorpholine-1,1-dioxide
  • BAY 2502
  • Bayer 2502
  • CCRIS 2201
  • EINECS 245-531-0
  • Lampit
  • Nifurtimox
  • Nifurtimoxum
  • Nifurtimoxum [INN-Latin]
  • Tetrahydro-3-methyl-4-((5-nitrofurfurylidene)amino)-2H-1,4-thiazine 1,1-dioxide
  • UNII-M84I3K7C2O

Systematic Names

  • 4-((5-Nitrofurfurylidene)amino)-3-methylthiomorpholine 1,1-dioxide
  • 4-Thiomorpholinamine, 3-methyl-N-((5-nitro-2-furanyl)methylene)-, 1,1-dioxide
  • Nifurtimox
  • Thiomorpholine, 3-methyl-4-((5-nitrofurfurylidene)amino)-, 1,1-dioxide

Registry Numbers

CAS Registry Number

  • 23256-30-6

FDA UNII

  • M84I3K7C2O

System Generated Number

  • 0023256306

Structure Descriptors

InChI

1S/C10H13N3O5S/c1-8-7-19(16,17)5-4-12(8)11-6-9-2-3-10(18-9)13(14)15/h2-3,6,8H,4-5,7H2,1H3/b11-6+

InChIKey

ARFHIAQFJWUCFH-IZZDOVSWSA-N

Smiles

CC1CS(=O)(=O)CCN1/N=C/c2ccc(o2)[N+](=O)[O-]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral > 4gm/kg (4000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: NAUSEA OR VOMITING
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1590, 1972.
dog LD50 oral > 2gm/kg (2000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1590, 1972.
mouse LD50 intraperitoneal > 800mg/kg (800mg/kg)   Journal of Medicinal Chemistry. Vol. 18, Pg. 794, 1975.
mouse LD50 oral 2291mg/kg (2291mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Transactions of the Royal Society of Tropical Medicine and Hygiene. Vol. 74, Pg. 43, 1980.
rabbit LD50 oral 2gm/kg (2000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1590, 1972.
rat LD50 oral 4050mg/kg (4050mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1590, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 181 deg C   EXP
log P (octanol-water) -0.340 (none)   EST
Atmospheric OH Rate Constant 6.49E-11 cm3/molecule-sec 25 EST

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