Nifurtimox | CAS#23256-30-6 | MedKoo Biosciences

MedKoo Cat#: 205934 | Name: Nifurtimox

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Description:

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

Nifurtimox is a 5-nitrofuran and is used to treat diseases caused by trypanosomes including Chagas disease and sleeping sickness. It is given by mouth and not by injection. Nifurtimox is now in a Phase II clinical trial for the treatment of pediatric neuroblastoma and medulloblastoma. Nifurtimox decreased cell viability in a concentration-dependent manner. Nifurtimox also suppressed basal and TrkB-mediated Akt phosphorylation, and the cytotoxicity of nifurtimox was attenuated by a tyrosine hydroxylase inhibitor (alpha-methyl-tyrosine). Nifurtimox killed catecholaminergic, but not cholinergic, autonomic neurons in culture. In vivo xenograft models showed inhibition of tumor growth with a histologic decrease in proliferation and increase in apoptosis. These results suggest that nifurtimox induces cell death in neuroblastoma . Therefore, further studies are warranted to develop nifurtimox as a promising new treatment for neuroblastoma.

Chemical Structure

Nifurtimox

CAS#23256-30-6

Theoretical Analysis

MedKoo Cat#: 205934

Name: Nifurtimox

CAS#: 23256-30-6

Chemical Formula: C10H13N3O5S

Exact Mass: 287.0576

Molecular Weight: 287.29

Elemental Analysis: C, 41.81; H, 4.56; N, 14.63; O, 27.85; S, 11.16

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 250.00
10mg	USD 450.00
25mg	USD 850.00

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Related CAS #

No Data

Synonym

BAY 2502; Bayer 2502; Lampit.

IUPAC/Chemical Name

(E)-3-methyl-4-(((5-nitrofuran-2-yl)methylene)amino)thiomorpholine 1,1-dioxide

InChi Key

ARFHIAQFJWUCFH-IZZDOVSWSA-N

InChi Code

InChI=1S/C10H13N3O5S/c1-8-7-19(16,17)5-4-12(8)11-6-9-2-3-10(18-9)13(14)15/h2-3,6,8H,4-5,7H2,1H3/b11-6+

SMILES Code

O=[N+](C1=CC=C(/C=N/N2C(C)CS(CC2)(=O)=O)O1)[O-]

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, not in water

Shelf Life

>5 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

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Nifurtimox is an antiprotozoal agent. Nifurtimox affects enzyme activity of lactate dehydrogenase (LDH).

In vitro activity:

This study has found that nifurtimox preferentially kill clonogenic tumor cells especially under the hypoxic conditions of ≤0.1% O2. Mechanistically, nifurtimox becomes activated after tumor cells enter into a fully hypoxic state, as shown by the stabilization of the Hypoxia-Inducible Factor 1α (HIF-1α). Nifurtimox specifically induces the formation of 53BP1 foci, a hallmark of DNA double-stranded breaks, in hypoxic tumor cells. Reference: Am J Cancer Res. 2017 May 1;7(5):1084-1095. https://pubmed.ncbi.nlm.nih.gov/28560059/

In vivo activity:

The results exhibited that nifurtimox could competently hinder the development of astroglioma in the mouse brain as compared to temozolomide, the first line of drug for brain tumors. Meanwhile the surviving rate, as well as the body-weight was dramatically upregulated upon nifurtimox treatment, as compared to that of temozolomide. These findings offered nifurtimox as a better alternative drug in treating astroglioma in vivo. Reference: Curr Mol Med. 2020;20(9):723-732. https://pubmed.ncbi.nlm.nih.gov/32271693/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	104.42
	DMSO	75.7	263.38

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 287.29 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. Li Q, Lin Q, Kim H, Yun Z. The anti-protozoan drug nifurtimox preferentially inhibits clonogenic tumor cells under hypoxic conditions. Am J Cancer Res. 2017 May 1;7(5):1084-1095. PMID: 28560059; PMCID: PMC5446476. 2. Cabanillas Stanchi KM, Bruchelt G, Handgretinger R, Holzer U. Nifurtimox reduces N-Myc expression and aerobic glycolysis in neuroblastoma. Cancer Biol Ther. 2015;16(9):1353-63. doi: 10.1080/15384047.2015.1070987. Epub 2015 Jul 15. PMID: 26177922; PMCID: PMC4622434. 3. Zhang Q, Chen Z, Yuan W, Tang YQ, Zhu J, Wu W, Ren H, Wang H, Zheng W, Zhang Z, Kong E. Nifurtimox Hampered the Progression of Astroglioma In vivo Via Manipulating the AKT-GSK3β axis. Curr Mol Med. 2020;20(9):723-732. doi: 10.2174/1566524020666200409124258. PMID: 32271693. 4. Kong E, Zhu J, Wu W, Ren H, Jiao X, Wang H, Zhang Z. Nifurtimox Inhibits the Progression of Neuroblastoma in vivo. J Cancer. 2019 May 21;10(10):2194-2204. doi: 10.7150/jca.27851. PMID: 31258723; PMCID: PMC6584410.

In vitro protocol:

In vivo protocol:

1. Zhang Q, Chen Z, Yuan W, Tang YQ, Zhu J, Wu W, Ren H, Wang H, Zheng W, Zhang Z, Kong E. Nifurtimox Hampered the Progression of Astroglioma In vivo Via Manipulating the AKT-GSK3β axis. Curr Mol Med. 2020;20(9):723-732. doi: 10.2174/1566524020666200409124258. PMID: 32271693. 2. Kong E, Zhu J, Wu W, Ren H, Jiao X, Wang H, Zhang Z. Nifurtimox Inhibits the Progression of Neuroblastoma in vivo. J Cancer. 2019 May 21;10(10):2194-2204. doi: 10.7150/jca.27851. PMID: 31258723; PMCID: PMC6584410.

1: Singh RK, Dorf L, DeMartino A, Illenye S, Koto K, Currier EA, Ashikaga T, Kim KK, Brard L, Sholler GL. Oral RKS262 reduces tumor burden in a neuroblastoma xenograft animal model and mediates cytotoxicity through SAPK/JNK and ROS activation in vitro. Cancer Biol Ther. 2011 Jun 15;11(12):1036-45. Epub 2011 Jun 15. PubMed PMID: 21532338. 2: Koto KS, Lescault P, Brard L, Kim K, Singh RK, Bond J, Illenye S, Slavik MA, Ashikaga T, Saulnier Sholler GL. Antitumor activity of nifurtimox is enhanced with tetrathiomolybdate in medulloblastoma. Int J Oncol. 2011 May;38(5):1329-41. doi: 10.3892/ijo.2011.971. Epub 2011 Mar 10. PubMed PMID: 21399873. 3: Saulnier Sholler GL, Bergendahl GM, Brard L, Singh AP, Heath BW, Bingham PM, Ashikaga T, Kamen BA, Homans AC, Slavik MA, Lenox SR, Higgins TJ, Ferguson WS. A phase 1 study of nifurtimox in patients with relapsed/refractory neuroblastoma. J Pediatr Hematol Oncol. 2011 Jan;33(1):25-30. doi: 10.1097/MPH.0b013e3181f47061. PubMed PMID: 21063221. 4: Singh RK, Lange TS, Kim KK, Brard L. A coumarin derivative (RKS262) inhibits cell-cycle progression, causes pro-apoptotic signaling and cytotoxicity in ovarian cancer cells. Invest New Drugs. 2011 Feb;29(1):63-72. doi: 10.1007/s10637-009-9335-4. Epub 2009 Oct 29. PubMed PMID: 19865799. 5: Saulnier Sholler GL, Brard L, Straub JA, Dorf L, Illeyne S, Koto K, Kalkunte S, Bosenberg M, Ashikaga T, Nishi R. Nifurtimox induces apoptosis of neuroblastoma cells in vitro and in vivo. J Pediatr Hematol Oncol. 2009 Mar;31(3):187-93. doi: 10.1097/MPH.0b013e3181984d91. PubMed PMID: 19262245. 6: Saulnier Sholler GL, Kalkunte S, Greenlaw C, McCarten K, Forman E. Antitumor activity of nifurtimox observed in a patient with neuroblastoma. J Pediatr Hematol Oncol. 2006 Oct;28(10):693-5. PubMed PMID: 17023833.