Thiarabine

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

MedKoo CAT#: 205644

CAS#: 6599-17-7

Description: Thiarabine is a analog of antimetabolite cytarabine (ara-C), with potential antineoplastic activity. Upon administration, thiarabine (T-araC) is phosphorylated to the triphosphate form T-araCTP and competes with cytidine for incorporation into DNA. This results in an inhibition of DNA replication and RNA synthesis, chain termination and may eventually decrease tumor cell proliferation. Compared to ara-C, T-araC appears to have a longer half-life and has a higher efficacy.


Chemical Structure

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Thiarabine
CAS# 6599-17-7

Theoretical Analysis

MedKoo Cat#: 205644
Name: Thiarabine
CAS#: 6599-17-7
Chemical Formula: C9H13N3O4S
Exact Mass: 259.06268
Molecular Weight: 259.28
Elemental Analysis: C, 41.69; H, 5.05; N, 16.21; O, 24.68; S, 12.37

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Synonym: OSI 7836; OSI-7836; OSI7836; Thiarabine; 4-Thio1-Darabinofuranosylcytosine; 4-Thioaracytidine; Thio-Cytarabine

IUPAC/Chemical Name: 4-amino-1-((2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrothiophen-2-yl)pyrimidin-2(1H)-one

InChi Key: GAKJJSAXUFZQTL-CCXZUQQUSA-N

InChi Code: InChI=1S/C9H13N3O4S/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1

SMILES Code: O=C1N=C(N)C=CN1[C@H]2[C@@H](O)[C@H](O)[C@@H](CO)S2

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

Preparing Stock Solutions

The following data is based on the product molecular weight 259.28 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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1. New nucleoside analogs for patients with hematological malignancies By Robak, Tadeusz From Expert Opinion on Investigational Drugs (2011), 20(3), 343-359.

2. Use of alkylphosphocholines in combination with antimetabolites for the treatment of benign and malignant oncoses in humans and mammals By Engel, Juergen; Guenther, Eckhard; Sindermann, Herbert; Aicher, Babette From U.S. Pat. Appl. Publ. (2011), US 20110028421 A1 20110203.

3. Inhibition of herpesvirus replication by 5-substituted 4'-thiopyrimidine nucleosides By Prichard, Mark N.; Quenelle, Debra C.; Hartline, Caroll B.; Harden, Emma A.; Jefferson, Geraldine; Frederick, Samuel L.; Daily, Shannon L.; Whitley, Richard J.; Tiwari, Kamal N.; Maddry, Joseph A.; et al From Antimicrobial Agents and Chemotherapy (2009), 53(12), 5251-5258.

4. Enhancement of the in vivo antitumor activity of clofarabine by 1-β-d-[4-thio-arabinofuranosyl]-cytosine By Parker, William B.; Shaddix, Sue C.; Gilbert, Karen S.; Shepherd, Rodney V.; Waud, William R. From Cancer Chemotherapy and Pharmacology (2009), 64(2), 253-261.

5. Activities of certain 5-substituted 4'-thiopyrimidine nucleosides against orthopoxvirus infections By Kern, Earl R.; Prichard, Mark N.; Quenelle, Debra C.; Keith, Kathy A.; Tiwari, Kamal N.; Maddry, Joseph A.; Secrist, John A., III From Antimicrobial Agents and Chemotherapy (2009), 53(2), 572-579.

6. Method for treating and preventing arthritis By Secrist, John A.; Waud, William R.; Qu, Zhican; Cui, Xiangmin From U.S. Pat. Appl. Publ. (2008), US 20080234275 A1 20080925.

7. Cytotoxic activities of nucleoside and nucleobase analog drugs in malignant mesothelioma: Characterization of a novel nucleobase transport activity By Damaraju, Deepti; Damaraju, Vijaya L.; Brun, Miranda; Mowles, Delores; Kuzma, Michelle; Berendt, Richard C.; Sawyer, Michael B.; Cass, Carol E. From Biochemical Pharmacology (2008), 75(10), 1901-1911.

8. Nucleosides as anticancer agents: from concept to the clinic By Secrist, John A., III From Nucleic Acids Symposium Series (2005), (49), 15-16.

9. Antiangiogenic activity of 4'-thio-β-D-arabinofuranosylcytosine By Roy, Anshu M.; Tiwari, Kamal N.; Parker, William B.; Secrist, John A., III; Li, Rongbao; Qu, Zhican From Molecular Cancer Therapeutics (2006), 5(9), 2218-2224.

10. A phase I, first in man study of OSI-7836 in patients with advanced refractory solid tumors: IND.147, a study of the Investigational New Drug Program of the National Cancer Institute of Canada Clinical Trials Group By Goss, G.; Siu, L. L.; Gauthier, I.; Chen, E. X.; Oza, A. M.; Goel, R.; Maroun, J.; Powers, J.; Walsh, W.; Maclean, M.; et al From Cancer Chemotherapy and Pharmacology (2006), 58(5), 703-710.

11. The role of human nucleoside transporters in cellular uptake of 4'-thio-β-D-arabinofuranosylcytosine and β-D-arabinosylcytosine By Clarke, Marilyn L.; Damaraju, Vijaya L.; Zhang, Jing; Mowles, Delores; Tackaberry, Tracey; Lang, Thach; Smith, Kyla M.; Young, James D.; Tomkinson, Blake; Cass, Carol E. From Molecular Pharmacology (2006), 70(1), 303-310.

12. A phase I study of a new nucleoside analogue, OSI-7836, using two administration schedules in patients with advanced solid malignancies By Lee, Chooi P.; de Jonge, Maja J. A.; O'Donnell, Anne E.; Schothorst, Kristel L.; Hanwell, Janet; Chick, Jon B.; Brooimans, Rik A.; Adams, Laurel M.; Drolet, Daniel W.; de Bono, Johann S.; et al From Clinical Cancer Research (2006), 12(9), 2841-2848.

13. Long intracellular retention of 4'-thio-arabinofuranosylcytosine 5'-triphosphate as a critical factor for the anti-solid tumor activity of 4'-thio-arabinofuranosylcytosine By Someya, Hitoshi; Waud, William R.; Parker, William B. From Cancer Chemotherapy and Pharmacology (2006), 57(6), 772-780.

14. Safety Assessment of 4'-Thio-β-D-Arabinofuranosylcytosine in the Beagle Dog Suggests a Drug-Induced Centrally Mediated Effect on the Hypothalamic-Pituitary-Adrenal Axis By Colagiovanni, Dorothy B.; Drolet, Daniel W.; Dihel, Larry; Meyer, Dennis J.; Hart, Karen; Wolf, Julie From International Journal of Toxicology (2006), 25(2), 119-126.

15. Mechanism of action of 4'-thio-beta-D-arabinofuranosylcytosine By Someya, Hitoshi No Corporate Source data available (2005), 115 pp..

English, Database: CAPLUS Substances Reactions ~0 Citings Full Text Link 0 Comments 0 Tags 16. c-Abl-independent p73 stabilization during gemcitabine- or 4'-thio-β-D-arabinofuranosylcytosine-induced apoptosis in wild-type and p53-null colorectal cancer cells By Thottassery, Jaideep V.; Westbrook, Louise; Someya, Hitoshi; Parker, William B. From Molecular Cancer Therapeutics (2006), 5(2), 400-410.

17. Chemical and enzymatic synthesis of 4'-thio-β-D-arabinofuranosylcytosine monophosphate and triphosphate By Fowler, A. S.; Tiwari, K. N.; Campbell, S. R.; Secrist, J. A., III From Nucleosides, Nucleotides & Nucleic Acids (2005), 24(5-7), 533-537.

18. Bone marrow proliferation assay By Koratich, Michael S.; May, Richard D. From PCT Int. Appl. (2005), WO 2005026380 A2 20050324.

19. Incorporation of OSI-7836 into DNA of Calu-6 and H460 xenograft tumors By Richardson, Frank; Black, Chris; Richardson, Katherine; Franks, April; Wells, Edward; Karimi, Susan; Sennello, Gina; Hart, Karen; Meyer, Denny; Emerson, David; et al From Cancer Chemotherapy and Pharmacology (2005), 55(3), 213-221.

20. Polymerization of the triphosphates of AraC, 2',2'-difluorodeoxycytidine (dFdC) and OSI-7836 (T-araC) by human DNA polymerase α and DNA primase By Richardson, Katherine A.; Vega, Tanya P.; Richardson, Frank C.; Moore, Chad L.; Rohloff, John C.; Tomkinson, Blake; Bendele, Raymond A.; Kuchta, Robert D. From Biochemical Pharmacology (2004), 68(12), 2337-2346.

21. Preparation of bioreductively activated prodrugs of antiproliferative agents By Davis, Peter David; Naylor, Matthew Alexander; Thomson, Peter; Everett, Steven Albert; Stratford, Michael Richard Lacey; Wardman, Peter From PCT Int. Appl. (2004), WO 2004085421 A2 20041007.

22. Preclinical antitumor activity of 4'-thio-β-D-arabinofuranosylcytosine (4'-thio-ara-C) By Waud, William R.; Gilbert, Karen S.; Shepherd, Rodney V.; Montgomery, John A.; Secrist, John A. From Cancer Chemotherapy and Pharmacology (2003), 51(5), 422-426.

23. Phosphorylation of 4'-thio-β-D-arabinofuranosylcytosine and its analogs by human deoxycytidine kinase By Someya, Hitoshi; Shaddix, Sue C.; Tiwari, Kamal N.; Secrist, John A., III; Parker, William B. From Journal of Pharmacology and Experimental Therapeutics (2003), 304(3), 1314-1322.

24. Synthesis and structure activity relationships of 5-substituted - 4'-thio-β-D-arabinofuranosylcytosines By Tiwari, Kamal N.; Shortnacy-Fowler, Anita T.; Cappellacci, Loredana; Waud, William R.; Parker, William B.; Montgomery, John A.; Secrist, John A., III From Nucleosides, Nucleotides & Nucleic Acids (2000), 19(10-12), 2005-2017.

25. Metabolism of 4'-thio-β-d-arabinofuranosylcytosine in CEM cells By Parker, W. B.; Shaddix, S. C.; Rose, L. M.; Waud, W. R.; Shewach, D. S.; Tiwari, K. N.; Secrist, J. A. From Biochemical Pharmacology (2000), 60(12), 1925-1932.

26. Synthesis of 4'-thio-β-D-arabinofuranosylcytosine (4'-thio-ara-C) and comparison of its anticancer activity with that of ara-C By Tiwari, Kamal N.; Shortnacy-Fowler, Anita T.; Cappellacci, Loredana; Parker, William B.; Waud, William R.; Montgomery, John A.; Secrist, John A., III From Nucleosides, Nucleotides & Nucleic Acids (2000), 19(1 & 2), 329-340.

27. Preparation of thioarabinofuranosyl nucleosides as antitumors By Secrist, John A., III; Tiwari, Kamal N.; Montgomery, John A. From PCT Int. Appl. (2000), WO 2000004866 A2 20000203.

28. Preparation and antitumor activity of 4'-thio analogs of 2,2'-anhydro-1-β-D-arabinofuranosylcytosine By Ototani, N.; Whistler, Roy L. From Journal of Medicinal Chemistry (1974), 17(5), 535-7.

29. 4-Thio-D-arabinofuranosylpyrimidine nucleosides By Whistler, Roy L.; Doner, Landis W.; Nayak, Govindraj U. From Journal of Organic Chemistry (1971), 36(1), 108-10.



Additional Information

thiarabine is a analog of antimetabolite cytarabine (ara-C), with potential antineoplastic activity. Upon administration, thiarabine (T-araC) is phosphorylated to the triphosphate form T-araCTP and competes with cytidine for incorporation into DNA. This results in an inhibition of DNA replication and RNA synthesis, chain termination and may eventually decrease tumor cell proliferation. Compared to ara-C, T-araC appears to have a longer half-life and has a higher efficacy. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).
 
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