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

MedKoo CAT#: 206005

CAS#: 60084-10-8

Description: Tiazofurin is a synthetic nucleoside analogue with antineoplastic activity. Tiazofurin (TR) is anabolized intracellularly to an analogue of NAD, tiazole-4-carboxamide adenine dinucleotide (TAD), a potent inhibitor of IMP dehydrogenase (IMPDH); IMPDH is the rate-limiting enzyme for de novo purine synthesis. Inhibition of IMPDH results in reduced levels of guanylates, resulting in the inhibition tumor cell growth in vitro and in vivo.

Chemical Structure

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Tiazofurin
CAS# 60084-10-8
Instruction

Theoretical Analysis

MedKoo Cat#: 206005
Name: Tiazofurin
CAS#: 60084-10-8
Chemical Formula: C9H12N2O5S
Exact Mass: 260.05
Molecular Weight: 260.270
Elemental Analysis: C, 41.53; H, 4.65; N, 10.76; O, 30.74; S, 12.32

Price and Availability

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5mg USD 585
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Synonym: Tiazofurin; Riboxamide; TCAR.

IUPAC/Chemical Name: 2-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)thiazole-4-carboxamide

InChi Key: FVRDYQYEVDDKCR-DBRKOABJSA-N

InChi Code: InChI=1S/C9H12N2O5S/c10-8(15)3-2-17-9(11-3)7-6(14)5(13)4(1-12)16-7/h2,4-7,12-14H,1H2,(H2,10,15)/t4-,5-,6-,7-/m1/s1

SMILES Code: O=C(C1=CSC([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)=N1)N

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

More Info:         

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 260.27 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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 1: Popsavin M, Spaić S, Svirčev M, Kojić V, Bogdanović G, Popsavin V. Synthesis and in vitro antitumour screening of 2-(β-D-xylofuranosyl)thiazole-4-carboxamide and two novel tiazofurin analogues with substituted tetrahydrofurodioxol moiety as a sugar mimic. Bioorg Med Chem Lett. 2012 Nov 1;22(21):6700-4. doi: 10.1016/j.bmcl.2012.08.093. Epub 2012 Sep 3. PubMed PMID: 23010263.

2: Mironiuk-Puchalska E, Koszytkowska-Stawińska M, Sas W, De Clercq E, Naesens L. Synthesis of novel aza-analogues of tiazofurin with 2-[5,5-bis(hydroxymethyl)pyrrolidin-2-yl] framework as sugar mimic. Nucleosides Nucleotides Nucleic Acids. 2012;31(1):72-84. doi: 10.1080/15257770.2011.643848. PubMed PMID: 22257212.

3: Stojkov D, Lavrnja I, Pekovic S, Dacic S, Bjelobaba I, Mostarica-Stojkovic M, Stosic-Grujicic S, Jovanovic S, Nedeljkovic N, Rakic L, Stojiljkovic M. Therapeutic effects of combined treatment with ribavirin and tiazofurin on experimental autoimmune encephalomyelitis development: clinical and histopathological evaluation. J Neurol Sci. 2008 Apr 15;267(1-2):76-85. Epub 2007 Nov 8. PubMed PMID: 17996253.

4: Popsavin M, Spaić S, Svircev M, Kojić V, Bogdanović G, Popsavin V. Synthesis and antitumour activity of new tiazofurin analogues bearing a 2,3-anhydro functionality in the furanose ring. Bioorg Med Chem Lett. 2007 Aug 1;17(15):4123-7. Epub 2007 May 23. PubMed PMID: 17543526.

5: Panattoni A, D'Anna F, Triolo E. Antiviral activity of tiazofurin and mycophenolic acid against Grapevine leafroll-associated virus 3 in Vitis vinifera explants. Antiviral Res. 2007 Mar;73(3):206-11. Epub 2006 Nov 3. PubMed PMID: 17125850.

6: Horvath Z, Saiko P, Illmer C, Madlener S, Hoechtl T, Bauer W, Erker T, Jaeger W, Fritzer-Szekeres M, Szekeres T. Resveratrol, an ingredient of wine, acts synergistically with Ara-C and tiazofurin in HL-60 human promyelocytic leukemia cells. Nucleosides Nucleotides Nucleic Acids. 2006;25(9-11):1019-24. PubMed PMID: 17065057.

7: Popsavin M, Spaić S, Svircev M, Kojić V, Bogdanović G, Popsavin V. 2-(3-Amino-3-deoxy-beta-D-xylofuranosyl)thiazole-4-carboxamide: a new tiazofurin analogue with potent antitumour activity. Bioorg Med Chem Lett. 2006 Oct 15;16(20):5317-20. PubMed PMID: 16908146.

8: Pejanović V, Piperski V, Ugljesić-Kilibarda D, Tasić J, Dacević M, Medić-Mijacević L, Gunić E, Popsavin M, Popsavin V. Synthesis and biological activity of some new 5'-O-acyl tiazofurin derivatives. Eur J Med Chem. 2006 Apr;41(4):503-12. Epub 2006 Mar 7. PubMed PMID: 16519966.

9: Popsavin M, Torović L, Svircev M, Kojić V, Bogdanović G, Popsavin V. Synthesis and antiproliferative activity of two new tiazofurin analogues with 2'-amido functionalities. Bioorg Med Chem Lett. 2006 May 15;16(10):2773-6. Epub 2006 Feb 21. PubMed PMID: 16495053.

10: Chun MW, Kim MJ, Shin JH, Jeong LS. Synthesis of 3'-deoxy-3'-C-hydroxymethyl analogues of tiazofurin and ribavirin. Nucleosides Nucleotides Nucleic Acids. 2005;24(5-7):975-7. PubMed PMID: 16248075.