WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 205934
CAS#: 23256-30-6
Description: 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.
MedKoo Cat#: 205934
Name: Nifurtimox
CAS#: 23256-30-6
Chemical Formula: C10H13N3O5S
Exact Mass: 287.05759
Molecular Weight: 287.29
Elemental Analysis: C, 41.81; H, 4.56; N, 14.63; O, 27.85; S, 11.16
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
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 |
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.
