Nifuroxazide

Names

[ CAS No. ]:
965-52-6

[ Name ]:
Nifuroxazide

[Synonym ]:
Benzoic acid, 4-hydroxy-, 2-[(1E)-(5-nitro-2-furanyl)methylene]hydrazide
Nifuroxazide
Ercefuryl
Diarlidan
Dicoferin
EINECS 213-522-0
Nifuroxazid
Nifuroxazidum
4-Hydroxy-N'-[(E)-(5-nitro-2-furyl)methylene]benzohydrazide
Nifuroxazida
p-hydroxy-N'-(5-nitrofurfurylidene)benzhydrazide
MFCD00079482
Nifuroxazidum [INN-Latin]
Ercefurol

Biological Activity

[Description]:

Nifuroxazide is an effective inhibitor of STAT3, also exerts potent anti-tumor and anti-metastasis activity.

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

[Target]

STAT3

[In Vitro]

When U266 cells are incubated with Nifuroxazide, a significant dose-dependent decrease in STAT3 tyrosine phosphorylation is observed. This inhibition of STAT3 tyrosine phosphorylation is rapid, occurring as early as 1 h after treatment, and is sustained for at least 24 h. Treatment of U266 or INA6 cells with Nifuroxazide for 48 hours result in a dose-dependent loss of cell viability with an EC50 of approximately 4.5 μM in both cell types. Notably, the MM cells lacking constitutive STAT3 activation show little toxicity to Nifuroxazide[1].

[In Vivo]

Compared with the vehicle group, treatment with Nifuroxazide could inhibit tumor growth and tumor weight in a dose-dependent manner, with the inhibition rate of tumor volumes being 43.0% and 62.1% at 25 mg/kg and 50 mg/kg, respectively. It is also shown that Nifuroxazide significantly inhibits the proliferation of nuclear Ki-67-positive cells and induces apoptosis cells of cleaved caspase-3-positive cells. Besides, it is found that treatment with Nifuroxazide could inhibit the expression of MMP-2, MMP-9 and p-Stat3 in A375 tumor tissues. What’s more, Nifuroxazide inhibits the infiltration of MDSCs into the lung, which might be associated with suppression of distant colonization of tumor cells in B16-F10 melanoma metastasis model[2].

[Animal admin]

Mice[2] Mice engrafted subcutaneously with 1×107 A375 cells are randomly divided into groups when tumor volume is around 100 mm3 and are administrated intraperitoneally injected with Nifuroxazide 25 mg/kg, 50 mg/kg or vehicle once daily. The tumor size and body weight are measured every 3 days. C57Bl/6J mice are engrafted by injecting intravenously via the tail vein with 2×105 B16-F10 cells to produce experimental lung metastasis. They are randomly assigned to groups on day 6 and are intraperitoneally injected with Nifuroxazide 50 mg/kg or vehicle once daily. Black dots on lung surface are counted and confirmed as melanoma metastases[2].

[References]

[1]. Nelson EA, et al. Nifuroxazide inhibits survival of multiple myeloma cells by directly inhibiting STAT3. Blood. 2008 Dec 15;112(13):5095-102.

[2]. Zhu Y, et al. Nifuroxazide exerts potent anti-tumor and anti-metastasis activity in melanoma. Sci Rep. 2016 Feb 2;6:20253.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Melting Point ]:
281-283°C

[ Molecular Formula ]:
C₁₂H₉N₃O₅

[ Molecular Weight ]:
275.217

[ Exact Mass ]:
275.054230

[ PSA ]:
120.65000

[ LogP ]:
0.59

[ Index of Refraction ]:
1.653

[ Storage condition ]:
Refrigerator, Under Inert Atmosphere

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DH2528300

CHEMICAL NAME :: Benzoic acid, p-hydroxy-, (5-nitrofurfurylidene)hydrazide

CAS REGISTRY NUMBER :: 965-52-6

LAST UPDATED :: 199612

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C12-H9-N3-O5

MOLECULAR WEIGHT :: 275.24

WISWESSER LINE NOTATION :: T5OJ BNW E1UNMVR DQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6 gm/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 :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Behavioral - antipsychotic Lungs, Thorax, or Respiration - respiratory depression Kidney, Ureter, Bladder - other changes in urine composition

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Bacteria - Escherichia coli

DOSE/DURATION :: 250 mg/L

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 187,55,1987

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DH2528300

[ HS Code ]:
2928000090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932190090

[ Summary ]:
2932190090 other compounds containing an unfused furan ring (whether or not hydrogenated) in the structure VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:20.0%

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