MedKoo Cat#: 206005 | Name: Tiazofurin
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Description:

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

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

Tiazofurin
Tiazofurin
CAS#60084-10-8

Theoretical Analysis

MedKoo Cat#: 206005

Name: Tiazofurin

CAS#: 60084-10-8

Chemical Formula: C9H12N2O5S

Exact Mass: 260.0467

Molecular Weight: 260.27

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 700.00
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Related CAS #
No Data
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
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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
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Broad-band luminescence involving fluconazole antifungal drug in a lead-free bismuth iodide perovskite: Combined experimental and computational insights. Spectrochim Acta A Mol Biomol Spectrosc. 2020 Aug 15;237:118354. doi: 10.1016/j.saa.2020.118354. Epub 2020 Apr 20. PMID: 32380432. 5: Kojić V, Popsavin M, Spaić S, Jakimov D, Kovačević I, Svirčev M, Aleksić L, Zelenović BS, Popsavin V. Structure based design, synthesis and in vitro antitumour activity of tiazofurin stereoisomers with nitrogen functions at the C-2' or C-3' positions. Eur J Med Chem. 2019 Dec 1;183:111712. doi: 10.1016/j.ejmech.2019.111712. Epub 2019 Sep 18. PMID: 31557614. 6: Kumawat MK. Thiazole Containing Heterocycles with Antimalarial Activity. Curr Drug Discov Technol. 2018;15(3):196-200. doi: 10.2174/1570163814666170725114159. PMID: 28745209. 7: Smee DF, Hurst BL, Evans WJ, Clyde N, Wright S, Peterson C, Jung KH, Day CW. Evaluation of cell viability dyes in antiviral assays with RNA viruses that exhibit different cytopathogenic properties. J Virol Methods. 2017 Aug;246:51-57. doi: 10.1016/j.jviromet.2017.03.012. Epub 2017 Mar 27. PMID: 28359770; PMCID: PMC5479350. 8: Isakovic AM, Dulovic M, Markovic I, Kravic-Stevovic T, Bumbasirevic V, Trajkovic V, Isakovic A. Autophagy suppression sensitizes glioma cells to IMP dehydrogenase inhibition-induced apoptotic death. Exp Cell Res. 2017 Jan 1;350(1):32-40. doi: 10.1016/j.yexcr.2016.11.001. Epub 2016 Nov 4. PMID: 27818246. 9: Chhabria MT, Patel S, Modi P, Brahmkshatriya PS. Thiazole: A Review on Chemistry, Synthesis and Therapeutic Importance of its Derivatives. Curr Top Med Chem. 2016;16(26):2841-2862. doi: 10.2174/1568026616666160506130731. PMID: 27150376. 10: Popsavin M, Kojić V, Torović L, Svirčev M, Spaić S, Jakimov D, Aleksić L, Bogdanović G, Popsavin V. Synthesis and in vitro antitumour activity of tiazofurin analogues with nitrogen functionalities at the C-2' position. Eur J Med Chem. 2016 Mar 23;111:114-25. doi: 10.1016/j.ejmech.2016.01.037. Epub 2016 Jan 25. PMID: 26859071. 11: De Clercq E. C-Nucleosides To Be Revisited. J Med Chem. 2016 Mar 24;59(6):2301-11. doi: 10.1021/acs.jmedchem.5b01157. Epub 2015 Oct 29. PMID: 26513594. 12: Pitaluga AN, Moreira ME, Traub-Csekö YM. A putative role for inosine 5' monophosphate dehydrogenase (IMPDH) in Leishmania amazonensis programmed cell death. Exp Parasitol. 2015 Feb;149:32-8. doi: 10.1016/j.exppara.2014.12.006. Epub 2014 Dec 9. PMID: 25499513. 13: Rouf A, Tanyeli C. Bioactive thiazole and benzothiazole derivatives. Eur J Med Chem. 2015 Jun 5;97:911-27. doi: 10.1016/j.ejmech.2014.10.058. Epub 2014 Oct 22. PMID: 25455640. 14: Li M, Su BS, Chang LH, Gao Q, Chen KL, An P, Huang C, Yang J, Li ZF. Oxymatrine induces apoptosis in human cervical cancer cells through guanine nucleotide depletion. Anticancer Drugs. 2014 Feb;25(2):161-73. doi: 10.1097/CAD.0000000000000012. PMID: 24231526. 15: Panattoni A, Rinaldelli E, Triolo E, Luvisi A. In vivo inhibition of trans- plasma membrane electron transport by antiviral drugs in grapevine. J Membr Biol. 2013 Jul;246(7):513-8. doi: 10.1007/s00232-013-9572-5. Epub 2013 Jun 18. PMID: 23774971. 16: Kusumanchi P, Zhang Y, Jani MB, Jayaram NH, Khan RA, Tang Y, Antony AC, Jayaram HN. Nicotinamide mononucleotide adenylyltransferase2 overexpression enhances colorectal cancer cell-kill by Tiazofurin. Cancer Gene Ther. 2013 Jul;20(7):403-12. doi: 10.1038/cgt.2013.33. Epub 2013 Jun 14. PMID: 23764899. 17: 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. PMID: 23010263. 18: 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. PMID: 22257212. 19: Synesiou E, Fairbanks LD, Simmonds HA, Slominska EM, Smolenski RT, Carrey EA. 4-Pyridone-3-carboxamide-1-β-D-ribonucleoside triphosphate (4PyTP), a novel NAD metabolite accumulating in erythrocytes of uremic children: a biomarker for a toxic NAD analogue in other tissues? Toxins (Basel). 2011 Jun;3(6):520-37. doi: 10.3390/toxins3060520. Epub 2011 Jun 7. PMID: 22069723; PMCID: PMC3202843. 20: Jayaram HN, Kusumanchi P, Yalowitz JA. NMNAT expression and its relation to NAD metabolism. Curr Med Chem. 2011;18(13):1962-72. doi: 10.2174/092986711795590138. PMID: 21517776.