Nifuroxazide

Modify Date: 2024-01-02 18:35:52

Nifuroxazide Structure
Nifuroxazide structure
Common Name Nifuroxazide
CAS Number 965-52-6 Molecular Weight 275.217
Density 1.5±0.1 g/cm3 Boiling Point N/A
Molecular Formula C12H9N3O5 Melting Point 281-283°C
MSDS USA Flash Point N/A

 Use of Nifuroxazide


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

 Names

Name 4-hydroxy-N-[(E)-(5-nitrofuran-2-yl)methylideneamino]benzamide
Synonym More Synonyms

 Nifuroxazide Biological Activity

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

 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

 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%

 Articles28

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Genotoxicity of 2-nitro-7-methoxy-naphtho[2,1-b]furan (R7000): a case study with some considerations on nitrofurantoin and nifuroxazide.

Res. Microbiol. 153(7) , 427-34, (2002)

Two nitrofurans present broad-spectrum antimicrobial properties and some of them are used in human and veterinary medicine. Most of these molecules are mutagens and some of them were reported as carci...

 Synonyms

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
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