Nifurtimox

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Names

[ Name ]:
Nifurtimox

[Synonym ]:
EINECS 245-531-0
4-Thiomorpholinamine,3-methyl-N-((5-nitro-2-furanyl)methylene)-,1,1-dioxide
Lampit
Nifurtimoxum [INN-Latin]
Bayer 2502
BAY 2502
Nifurtimox [INN:BAN]
4-(5-nitro-furfurylidene)amino-3-methylthiomorpholine 1,1-dioxide
NIFURTIMOX
3-methyl-4-[(5-nitrofurfurylidene)amino]thiomorpholine-1,1-dioxide
3-methyl-N-[(5-nitro-2-furanyl)methylene]-4-thiomorpholinamine-1,1-dioxide

Chemical & Physical Properties

[ Density]:
1.56g/cm3

[ Boiling Point ]:
550.3ºC at 760mmHg

[ Molecular Formula ]:
C₁₀H₁₃N₃O₅S

[ Molecular Weight ]:
287.29200

[ Flash Point ]:
286.6ºC

[ Exact Mass ]:
287.05800

[ PSA ]:
117.08000

[ LogP ]:
2.18250

[ Vapour Pressure ]:
3.7E-12mmHg at 25°C

[ Index of Refraction ]:
1.653

[ Storage condition ]:
2-8℃

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XM3020000

CHEMICAL NAME :: Thiomorpholine, 3-methyl-4-((5-nitrofurfurylidene)amino)-, 1,1-dioxide

CAS REGISTRY NUMBER :: 23256-30-6

LAST UPDATED :: 199706

DATA ITEMS CITED :: 25

MOLECULAR FORMULA :: C10-H13-N3-O5-S

MOLECULAR WEIGHT :: 287.32

WISWESSER LINE NOTATION :: T6N DSWTJ B1 ANU1- BT5OJ ENW

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4050 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2291 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Gastrointestinal - nausea or vomiting

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 11700 mg/kg/47W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Endocrine - adrenal cortex tumors Skin and Appendages - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 11700 mg/kg/47W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Endocrine - thyroid tumors Skin and Appendages - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2520 mg/kg

SEX/DURATION :: male 70 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 500 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 9100 mg/kg

SEX/DURATION :: male 91 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 100 mg/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1250 mg/kg

SEX/DURATION :: female 6-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3136 mg/kg

SEX/DURATION :: male 14 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2 gm/kg

SEX/DURATION :: male 8 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count)

TYPE OF TEST :: Specific locus test

TYPE OF TEST :: Cytogenetic analysis

TYPE OF TEST :: Sperm Morphology

TYPE OF TEST :: Micronucleus test

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 2 gm/kg

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 188,129,1987

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

3-methylthiomorpholin-4-amine 1,1-dioxide
5-Nitrofuraldehyde

DownStream

Articles

Trypanocidal Activity of Long Chain Diamines and Aminoalcohols.

Molecules 20 , 11554-68, (2015)

Thirteen aminoalcohols and eight diamines were obtained and tested against Trypanosoma cruzi epimastigotes strains MG, JEM and CL-B5 clone. Some of them were equal or more potent (1.0-6.6 times) than ...

American Trypanosomiasis (Chagas Disease)

Infect. Dis. Clin. North Am. 26(2) , 275-91, (2012)

Chagas disease, also known as American trypanosomiasis, is a chronic infection caused by Trypanosoma cruzi, a protozoan parasite. It is transmitted to human beings mainly through the feces of infected...

Targeting the substrate preference of a type I nitroreductase to develop antitrypanosomal quinone-based prodrugs.

Antimicrob. Agents Chemother. 56(11) , 5821-30, (2012)

Nitroheterocyclic prodrugs are used to treat infections caused by Trypanosoma cruzi and Trypanosoma brucei. A key component in selectivity involves a specific activation step mediated by a protein hom...

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