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965-52-6

965-52-6 structure
965-52-6 structure
  • Name: Nifuroxazide
  • Chemical Name: 4-hydroxy-N-[(E)-(5-nitrofuran-2-yl)methylideneamino]benzamide
  • CAS Number: 965-52-6
  • Molecular Formula: C12H9N3O5
  • Molecular Weight: 275.217
  • Catalog: API Antibiotics Other antibiotics
  • Create Date: 2018-03-04 08:00:00
  • Modify Date: 2025-08-22 11:24:18
  • Nifuroxazide is an effective inhibitor of STAT3, also exerts potent anti-tumor and anti-metastasis activity.
Name 4-hydroxy-N-[(E)-(5-nitrofuran-2-yl)methylideneamino]benzamide
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
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.
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

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
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
Precursor  4

DownStream  0

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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