Nifuroxazide-d4 | CAS#1188487-83-3 | Nifuroxazide quantification internal standard

MedKoo Cat#: 463923 | Name: Nifuroxazide-d4

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Nifuroxazide-d4 is intended for use as an internal standard for the quantification of nifuroxazide by GC- or LC-MS. Nifuroxazide is a nitrofuran antibiotic. It is active against strains of the enteropathogenic bacteria C. jejuni, Salmonella, Y. enterocolitica, Shigella, and E. coli. It inhibits quorum sensing and virulence factor production in P. aeruginosa. Nifuroxazide inhibits STAT3 activity in a reporter assay and decreases viability of U266 and INA-6 myeloma cells, which have constitutive STAT3 phosphorylation, with EC50 values of approximately 4.5 µM for both. It also decreases viability, migration, and invasion of, and induces apoptosis in, MCF-7, 4T1, and MDA-MB-231 breast cancer cells. Nifuroxazide reduces tumor growth and prevents pulmonary metastasis in a 4T1 murine mammary carcinoma model. It also reduces diarrhea, weight loss, and colon inflammation in a rat model of acetic acid-induced ulcerative colitis.

Chemical Structure

Nifuroxazide-d4

CAS#1188487-83-3

Theoretical Analysis

MedKoo Cat#: 463923

Name: Nifuroxazide-d4

CAS#: 1188487-83-3

Chemical Formula: C12H5D4N3O5

Exact Mass: 279.0793

Molecular Weight: 279.24

Elemental Analysis: C, 51.61; H, 4.69; N, 15.05; O, 28.65

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 550.00	2 Weeks
5mg	USD 1,250.00	2 Weeks

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Synonym

Nifuroxazide-d4; Nifuroxazide d4;

IUPAC/Chemical Name

(E)-4-hydroxy-N'-((5-nitrofuran-2-yl)methylene)benzohydrazide-2,3,5,6-d4

InChi Key

YCWSUKQGVSGXJO-WNGOOFDKSA-N

InChi Code

InChI=1S/C12H9N3O5/c16-9-3-1-8(2-4-9)12(17)14-13-7-10-5-6-11(20-10)15(18)19/h1-7,16H,(H,14,17)/b13-7+/i1D,2D,3D,4D

SMILES Code

O=C(N/N=C/C1=CC=C(O1)[N+]([O-])=O)C2=C(C([2H])=C(O)C([2H])=C2[2H])[2H]

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Nifuroxazide is an effective inhibitor of STAT3.

In vitro activity:

Nifuroxazide inhibits the constitutive phosphorylation of STAT3 in MM (multiple myeloma) cells by reducing Jak kinase autophosphorylation, and leads to down-regulation of the STAT3 target gene Mcl-1. Nifuroxazide causes a decrease in viability of primary myeloma cells and myeloma cell lines containing STAT3 activation, but not normal peripheral blood mononuclear cells. Although bone marrow stromal cells provide survival signals to myeloma cells, nifuroxazide can overcome this survival advantage. Reference: Blood. 2008 Dec 15;112(13):5095-102. https://pubmed.ncbi.nlm.nih.gov/18824601/

In vivo activity:

Nifuroxazide significantly inhibited tumor growth without obvious side effects in the A375-bearing mice model by inducing apoptosis and reducing cell proliferation and metastasis. Notably, nifuroxazide significantly inhibited pulmonary metastases, which might be associated with the decrease of myeloid-derived suppressor cells (MDSCs). Reference: Sci Rep. 2016 Feb 2;6:20253. https://pubmed.ncbi.nlm.nih.gov/26830149/

Preparing Stock Solutions

The following data is based on the product molecular weight 279.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Wang X, Ye J, Gao M, Zhang D, Jiang H, Zhang H, Zhao S, Liu X. Nifuroxazide inhibits the growth of glioblastoma and promotes the infiltration of CD8 T cells to enhance antitumour immunity. Int Immunopharmacol. 2023 Mar 14;118:109987. doi: 10.1016/j.intimp.2023.109987. Epub ahead of print. PMID: 36924564. 2. Nelson EA, Walker SR, Kepich A, Gashin LB, Hideshima T, Ikeda H, Chauhan D, Anderson KC, Frank DA. Nifuroxazide inhibits survival of multiple myeloma cells by directly inhibiting STAT3. Blood. 2008 Dec 15;112(13):5095-102. doi: 10.1182/blood-2007-12-129718. Epub 2008 Sep 29. PMID: 18824601; PMCID: PMC2597607. 3. Amin FM, Sharawy MH, Amin MN, El-Sherbiny M, Said E, Salem HA, Ibrahim TM. Nifuroxazide mitigates doxorubicin-induced cardiovascular injury: Insight into oxidative/NLRP3/GSDMD-mediated pyroptotic signaling modulation. Life Sci. 2023 Feb 1;314:121311. doi: 10.1016/j.lfs.2022.121311. Epub 2022 Dec 19. PMID: 36549350. 4. Zhu Y, Ye T, Yu X, Lei Q, Yang F, Xia Y, Song X, Liu L, Deng H, Gao T, Peng C, Zuo W, Xiong Y, Zhang L, Wang N, Zhao L, Xie Y, Yu L, Wei Y. Nifuroxazide exerts potent anti-tumor and anti-metastasis activity in melanoma. Sci Rep. 2016 Feb 2;6:20253. doi: 10.1038/srep20253. Erratum in: Sci Rep. 2022 Jun 28;12(1):10920. PMID: 26830149; PMCID: PMC4735744.

In vitro protocol:

In vivo protocol:

1. Amin FM, Sharawy MH, Amin MN, El-Sherbiny M, Said E, Salem HA, Ibrahim TM. Nifuroxazide mitigates doxorubicin-induced cardiovascular injury: Insight into oxidative/NLRP3/GSDMD-mediated pyroptotic signaling modulation. Life Sci. 2023 Feb 1;314:121311. doi: 10.1016/j.lfs.2022.121311. Epub 2022 Dec 19. PMID: 36549350. 2. Zhu Y, Ye T, Yu X, Lei Q, Yang F, Xia Y, Song X, Liu L, Deng H, Gao T, Peng C, Zuo W, Xiong Y, Zhang L, Wang N, Zhao L, Xie Y, Yu L, Wei Y. Nifuroxazide exerts potent anti-tumor and anti-metastasis activity in melanoma. Sci Rep. 2016 Feb 2;6:20253. doi: 10.1038/srep20253. Erratum in: Sci Rep. 2022 Jun 28;12(1):10920. PMID: 26830149; PMCID: PMC4735744.

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Bioorg Med Chem. 2020 Aug 30;28(22):115710. doi: 10.1016/j.bmc.2020.115710. Epub ahead of print. PMID: 33007545. 5: El-Far YM, Elsherbiny NM, El-Shafey M, Said E. The interplay of the inhibitory effect of nifuroxazide on NF-κB/STAT3 signaling attenuates acetic acid-induced ulcerative colitis in rats. Environ Toxicol Pharmacol. 2020 Oct;79:103433. doi: 10.1016/j.etap.2020.103433. Epub 2020 Jun 9. PMID: 32526270. 6: Khodir AE, Samra YA, Said E. A novel role of nifuroxazide in attenuation of sepsis-associated acute lung and myocardial injuries; role of TLR4/NLPR3/IL-1β signaling interruption. Life Sci. 2020 Sep 1;256:117907. doi: 10.1016/j.lfs.2020.117907. Epub 2020 Jun 3. PMID: 32504751. 7: Khodir AE, Said E. Nifuroxazide attenuates experimentally-induced hepatic encephalopathy and the associated hyperammonemia and cJNK/caspase-8/TRAIL activation in rats. Life Sci. 2020 Jul 1;252:117610. doi: 10.1016/j.lfs.2020.117610. Epub 2020 Apr 4. PMID: 32259601. 8: Hindupur SV, Schmid SC, Koch JA, Youssef A, Baur EM, Wang D, Horn T, Slotta- Huspenina J, Gschwend JE, Holm PS, Nawroth R. STAT3/5 Inhibitors Suppress Proliferation in Bladder Cancer and Enhance Oncolytic Adenovirus Therapy. Int J Mol Sci. 2020 Feb 7;21(3):1106. doi: 10.3390/ijms21031106. PMID: 32046095; PMCID: PMC7043223. 9: Chen D, Delmas JM, Hurtaud-Pessel D, Verdon E. Development of a multi-class method to determine nitroimidazoles, nitrofurans, pharmacologically active dyes and chloramphenicol in aquaculture products by liquid chromatography-tandem mass spectrometry. Food Chem. 2020 May 1;311:125924. doi: 10.1016/j.foodchem.2019.125924. Epub 2019 Dec 3. PMID: 31865112. 10: Luo L, Xu F, Peng H, Luo Y, Tian X, Battaglia G, Zhang H, Gong Q, Gu Z, Luo K. Stimuli-responsive polymeric prodrug-based nanomedicine delivering nifuroxazide and doxorubicin against primary breast cancer and pulmonary metastasis. J Control Release. 2020 Feb;318:124-135. doi: 10.1016/j.jconrel.2019.12.017. Epub 2019 Dec 12. PMID: 31838206. 11: Tsai CH, Lee Y, Li CH, Cheng YW, Kang JJ. Down-regulation of aryl hydrocarbon receptor intensifies carcinogen-induced retinal lesion via SOCS3-STAT3 signaling. Cell Biol Toxicol. 2020 Jun;36(3):223-242. doi: 10.1007/s10565-019-09499-z. Epub 2019 Nov 20. PMID: 31748929. 12: Zhao T, Feng Y, Guo M, Zhang C, Wu Q, Chen J, Guo S, Liu S, Zhou Q, Wang Z, Fan W, Zhang Y, Jia H, Feng Z. Combination of attenuated Salmonella carrying PD-1 siRNA with nifuroxazide for colon cancer therapy. J Cell Biochem. 2020 Feb;121(2):1973-1985. doi: 10.1002/jcb.29432. Epub 2019 Nov 6. PMID: 31692041. 13: Kim BH, Lee H, Song Y, Park JS, Gadhe CG, Choi J, Lee CG, Pae AN, Kim S, Ye SK. Development of Oxadiazole-Based ODZ10117 as a Small-Molecule Inhibitor of STAT3 for Targeted Cancer Therapy. J Clin Med. 2019 Nov 2;8(11):1847. doi: 10.3390/jcm8111847. 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