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MedKoo Cat#: 562662 | Name: Desferrithiocin

Description:

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

Desferrithiocin is an orally effective Fe chelator that is more active than desferrioxamine.

Chemical Structure

Desferrithiocin
Desferrithiocin
CAS#105635-60-6

Theoretical Analysis

MedKoo Cat#: 562662

Name: Desferrithiocin

CAS#: 105635-60-6

Chemical Formula: C10H9N2NaO3S

Exact Mass:

Molecular Weight: 260.24

Elemental Analysis: C, 46.15; H, 3.49; N, 10.76; Na, 8.83; O, 18.44; S, 12.32

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Desferrithiocin; DFT;
IUPAC/Chemical Name
(S)-4,5-Dihydro-2-(3-hydroxy-2-pyridinyl)-4-methyl-4-thiazolecarboxylic acid monosodium salt
InChi Key
UGJSEILLHZKUBG-HNCPQSOCSA-M
InChi Code
InChI=1S/C10H10N2O3S.Na/c1-10(9(14)15)5-16-8(12-10)7-6(13)3-2-4-11-7;/h2-4,13H,5H2,1H3,(H,14,15);/q;+1/p-1/t10-;/m1./s1
SMILES Code
O=C([C@]1(C)N=C(C2=NC=CC=C2O)SC1)[O-].[Na+]
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

Preparing Stock Solutions

The following data is based on the product molecular weight 260.24 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.

Recalculate based on batch purity %
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: Taher AT, Saliba AN, Kuo KH, Giardina PJ, Cohen AR, Neufeld EJ, Aydinok Y, Kwiatkowski JL, Jeglinski BI, Pietropaolo K, Berk G, Viprakasit V. Safety and pharmacokinetics of the oral iron chelator SP-420 in β-thalassemia. Am J Hematol. 2017 Dec;92(12):1356-1361. doi: 10.1002/ajh.24914. Epub 2017 Oct 31. PubMed PMID: 28940308. 2: Kaviani S, Izadyar M, Housaindokht MR. A DFT study on the complex formation between desferrithiocin and metal ions (Mg(2+), Al(3+), Ca(2+), Mn(2+), Fe(3+), Co(2+), Ni(2+), Cu(2+), Zn(2+)). Comput Biol Chem. 2017 Apr;67:114-121. doi: 10.1016/j.compbiolchem.2016.12.012. Epub 2017 Jan 3. PubMed PMID: 28068516. 3: Bergeron RJ, Bharti N, McManis JS, Wiegand J. Metabolically programmed iron chelators. Bioorg Med Chem. 2015 Sep 1;23(17):5954-71. doi: 10.1016/j.bmc.2015.06.059. Epub 2015 Jun 29. PubMed PMID: 26231739; PubMed Central PMCID: PMC4608554. 4: Hider RC, Kong X, Abbate V, Harland R, Conlon K, Luker T. Deferitazole, a new orally active iron chelator. Dalton Trans. 2015 Mar 21;44(11):5197-204. doi: 10.1039/c5dt00063g. PubMed PMID: 25687725. 5: Bergeron RJ, Wiegand J, McManis JS, Bharti N. Desferrithiocin: a search for clinically effective iron chelators. J Med Chem. 2014 Nov 26;57(22):9259-91. doi: 10.1021/jm500828f. Epub 2014 Sep 10. Review. PubMed PMID: 25207964; PubMed Central PMCID: PMC4255733. 6: Bergeron RJ, Wiegand J, Bharti N, McManis JS. Substituent effects on desferrithiocin and desferrithiocin analogue iron-clearing and toxicity profiles. J Med Chem. 2012 Aug 23;55(16):7090-103. doi: 10.1021/jm300509y. Epub 2012 Aug 13. PubMed PMID: 22889170; PubMed Central PMCID: PMC3583384. 7: Bergeron RJ, Wiegand J, Bharti N, McManis JS, Singh S. Desferrithiocin analogue iron chelators: iron clearing efficiency, tissue distribution, and renal toxicity. Biometals. 2011 Apr;24(2):239-58. doi: 10.1007/s10534-010-9389-y. Epub 2010 Nov 20. PubMed PMID: 21103911; PubMed Central PMCID: PMC3329216. 8: Bergeron RJ, Bharti N, Wiegand J, McManis JS, Singh S, Abboud KA. The impact of polyether chain length on the iron clearing efficiency and physiochemical properties of desferrithiocin analogues. J Med Chem. 2010 Apr 8;53(7):2843-53. doi: 10.1021/jm9018146. PubMed PMID: 20232803; PubMed Central PMCID: PMC2951135. 9: Bergeron RJ, Wiegand J, Singh S. Desferrithiocin analogue uranium decorporation agents. Int J Radiat Biol. 2009 Apr;85(4):348-61. doi: 10.1080/09553000902781089. PubMed PMID: 19399680; PubMed Central PMCID: PMC2861555. 10: Bergeron RJ, Wiegand J, McManis JS, Bharti N, Singh S. Desferrithiocin analogues and nephrotoxicity. J Med Chem. 2008 Oct 9;51(19):5993-6004. doi: 10.1021/jm8003398. Epub 2008 Sep 13. PubMed PMID: 18788724; PubMed Central PMCID: PMC2778308. 11: Barton JC. Drug evaluation: Deferitrin for iron overload disorders. IDrugs. 2007 Jul;10(7):480-90. PubMed PMID: 17642018. 12: Barton JC. Drug evaluation: deferitrin (GT-56-252; NaHBED) for iron overload disorders. IDrugs. 2007 Apr;10(4):270-81. Review. PubMed PMID: 17390251. 13: Bergeron RJ, Wiegand J, McManis JS, Vinson JR, Yao H, Bharti N, Rocca JR. (S)-4,5-dihydro-2-(2-hydroxy-4-hydroxyphenyl)-4-methyl-4-thiazolecarboxylic acid polyethers: a solution to nephrotoxicity. J Med Chem. 2006 May 4;49(9):2772-83. PubMed PMID: 16640338; PubMed Central PMCID: PMC2547084. 14: Hider RC, Zhou T. The design of orally active iron chelators. Ann N Y Acad Sci. 2005;1054:141-54. PubMed PMID: 16339660. 15: Bergeron RJ, Wiegand J, McManis JS, Weimar WR, Park JH, Eiler-McManis E, Bergeron J, Brittenham GM. Partition-variant desferrithiocin analogues: organ targeting and increased iron clearance. J Med Chem. 2005 Feb 10;48(3):821-31. PubMed PMID: 15689166. 16: Buss JL, Greene BT, Turner J, Torti FM, Torti SV. Iron chelators in cancer chemotherapy. Curr Top Med Chem. 2004;4(15):1623-35. Review. PubMed PMID: 15579100. 17: Brittenham GM. Iron chelators and iron toxicity. Alcohol. 2003 Jun;30(2):151-8. Review. PubMed PMID: 12957300. 18: Bergeron RJ, Wiegand J, Weimar WR, McManis JS, Smith RE, Abboud KA. Iron chelation promoted by desazadesferrithiocin analogs: An enantioselective barrier. Chirality. 2003 Aug;15(7):593-9. PubMed PMID: 12840823. 19: Nick H, Acklin P, Lattmann R, Buehlmayer P, Hauffe S, Schupp J, Alberti D. Development of tridentate iron chelators: from desferrithiocin to ICL670. Curr Med Chem. 2003 Jun;10(12):1065-76. Review. PubMed PMID: 12678677. 20: Lovejoy DB, Richardson DR. Iron chelators as anti-neoplastic agents: current developments and promise of the PIH class of chelators. Curr Med Chem. 2003 Jun;10(12):1035-49. Review. PubMed PMID: 12678675.