CAS 23256-30-6|Nifurtimox

Introduction：Basic information about CAS 23256-30-6|Nifurtimox, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Nifurtimox BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Articles28
7. Synonyms

Common Name	Nifurtimox
CAS Number	23256-30-6	Molecular Weight	287.29200
Density	1.56g/cm3	Boiling Point	550.3ºC at 760mmHg
Molecular Formula	C₁₀H₁₃N₃O₅S	Melting Point	/
MSDS	ChineseUSA	Flash Point	286.6ºC

Names

Name	(E)-N-(3-methyl-1,1-dioxo-1,4-thiazinan-4-yl)-1-(5-nitrofuran-2-yl)methanimine
Synonym	More Synonyms

Nifurtimox BiologicalActivity

Description	Nifurtimox, an antiprotozoal agent, which is generally used for the treatment of infections with Trypanosoma cruzi, has been used in the therapy of neuroblastoma. Nifurtimox affects enzyme activity of lactate dehydrogenase (LDH).
Related Catalog	Signaling Pathways >>Metabolic Enzyme/Protease >>Lactate DehydrogenaseSignaling Pathways >>Anti-infection >>ParasiteResearch Areas >>InfectionResearch Areas >>Cancer
Target	Trypanosoma cruzi[1] Lactate dehydrogenase (LDH) [1]
In Vitro	Nifurtimox affects enzyme activity of lactate dehydrogenase (LDH). To differentiate if this effect is a result of a reduced LDH activity or a shift in pyruvate metabolism due to activation of PDH, the enzyme activity of LDH is determined after 4 h treatment with 50 µg/mL Nifurtimox. Compared to the untreated control, the LDH activity is significantly reduced for LA-N-1 (P=0.005), IMR-32 (P=0.009), LS (P=0.0035) and SK-N-SH (P=0.0065). Nifurtimox reduces cell viability and induces cell cycle arrest and apoptosis in neuroblastoma cells. To characterize the cytotoxic impacts of Nifurtimox on neuroblastoma, 4 cell lines are subjected to several experiments. Cell viability is reduced for all 4 neuroblastoma cell lines after 24 h incubation with 50 µg/mL to an average of 66%, 63%, 62% and 75% (LA-N-1, IMR-32 LS and SK-N-SH, respectively). The reduction is significant compared to the untreated control (P<0.01) and the vehicle control with DMSO (P<0.05) for all cell lines[1].
Cell Assay	The Neuroblastoma cell lines IMR-32, LA-N-1 and SK-N-SH and the neuroblastoma cell line LS are grown in RPMI-1640 medium supplemented with 10% (v/v) fetal calf serum (FCS), 2 mM L-glutamine, 100 U/mL Penicillin and 100 µg/mL Streptomycin and incubated at 37°C, 5% CO2 and saturated humidity. To assess the cell viability after incubation with Nifurtimox at different concentrations (10 µg/mL up to 50 µg/mL or 34.8 µM to 174 µM, respectively in the supernatant growth medium) or the vehicle control with according concentrations, all neuroblastoma cell lines are subjected to an MTS assay. Stock solutions of MTS are made at 480 µM in sterile filtered deionized water and stored at -20°C. Cells are grown to approximately 50% confluency, treated with Nifurtimox, and incubated for 1 h with fresh media containing 12 µM MTS[1].
References	[1]. Cabanillas Stanchi KM, et al. Nifurtimox reduces N-Myc expression and aerobic glycolysis in neuroblastoma. Cancer Biol Ther. 2015;16(9):1353-63.

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
InChIKey	ARFHIAQFJWUCFH-WDZFZDKYSA-N
SMILES	CC1CS(=O)(=O)CCN1N=Cc1ccc([N+](=O)[O-])o1
Storage condition	2-8℃

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

Articles28

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...

Synonyms

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

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