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MedKoo Cat#: 205644 | Name: Thiarabine free base

Description:

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

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

Thiarabine free base
Thiarabine free base
CAS#26599-17-7 (free base)

Theoretical Analysis

MedKoo Cat#: 205644

Name: Thiarabine free base

CAS#: 26599-17-7 (free base)

Chemical Formula: C9H13N3O4S

Exact Mass: 259.0627

Molecular Weight: 259.28

Elemental Analysis: C, 41.69; H, 5.05; N, 16.21; O, 24.68; S, 12.37

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 #
26599-17-7 (free base) 1060763-87-2 (HCl) 1060763-85-0 (hydrate)
Synonym
4’-Thioaracytidine; OSI 7836; OSI 7836; OSI7836; Thiarabine; 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
More Info
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).   Current developer:    Access Pharmaceuticals    

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
1: Parker WB, Waud WR, Secrist JA 3rd. Thiarabine, 1-(4-Thio-β-D- arabinofuranosyl)cytosine. A Deoxycytidine Analog With Excellent Anticancer Activity. Curr Med Chem. 2015;22(34):3881-96. doi: 10.2174/092986732234151119153534. PMID: 26597061. 2: Waud WR, Gilbert KS, Secrist JA 3rd. Preclinical antitumor activity of thiarabine in human leukemia and lymphoma xenograft models. Nucleosides Nucleotides Nucleic Acids. 2012;31(9):647-60. doi: 10.1080/15257770.2012.710768. PMID: 23004929. 3: Waud WR, Gilbert KS, Secrist JA 3rd. Preclinical combination therapy of thiarabine plus various clinical anticancer agents. Nucleosides Nucleotides Nucleic Acids. 2012;31(8):630-46. doi: 10.1080/15257770.2012.712181. PMID: 22908953. 4: Waud WR, Parker WB, Gilbert KS, Secrist JA. Isolation and characterization of a murine P388 leukemia line resistant to thiarabine. Nucleosides Nucleotides Nucleic Acids. 2012;31(1):14-27. doi: 10.1080/15257770.2011.637099. PMID: 22257207. 5: Robak T. New nucleoside analogs for patients with hematological malignancies. Expert Opin Investig Drugs. 2011 Mar;20(3):343-59. doi: 10.1517/13543784.2011.554822. PMID: 21320002. 6: Waud WR, Gilbert KS, Secrist JA 3rd. Lack of in vivo cross-resistance with 4'-thio-ara-C against drug-resistant murine P388 and L1210 leukemias. Cancer Chemother Pharmacol. 2011 Aug;68(2):399-403. doi: 10.1007/s00280-010-1498-3. Epub 2010 Nov 11. PMID: 21069340; PMCID: PMC3128691. 7: Parker WB, Shaddix SC, Gilbert KS, Shepherd RV, Waud WR. Enhancement of the in vivo antitumor activity of clofarabine by 1-beta-D-[4-thio- arabinofuranosyl]-cytosine. Cancer Chemother Pharmacol. 2009 Jul;64(2):253-61. doi: 10.1007/s00280-008-0862-z. Epub 2008 Nov 11. PMID: 19002461. 8: Secrist JA 3rd. Nucleosides as anticancer agents: from concept to the clinic. Nucleic Acids Symp Ser (Oxf). 2005;(49):15-6. doi: 10.1093/nass/49.1.15. PMID: 17150610. 9: Roy AM, Tiwari KN, Parker WB, Secrist JA 3rd, Li R, Qu Z. Antiangiogenic activity of 4'-thio-beta-D-arabinofuranosylcytosine. Mol Cancer Ther. 2006 Sep;5(9):2218-24. doi: 10.1158/1535-7163.MCT-06-0048. PMID: 16985055. 10: Lee CP, de Jonge MJ, O'Donnell AE, Schothorst KL, Hanwell J, Chick JB, Brooimans RA, Adams LM, Drolet DW, de Bono JS, Kaye SB, Judson IR, Verweij J. A phase I study of a new nucleoside analogue, OSI-7836, using two administration schedules in patients with advanced solid malignancies. Clin Cancer Res. 2006 May 1;12(9):2841-8. doi: 10.1158/1078-0432.CCR-05-1932. PMID: 16675579. 11: Clarke ML, Damaraju VL, Zhang J, Mowles D, Tackaberry T, Lang T, Smith KM, Young JD, Tomkinson B, Cass CE. The role of human nucleoside transporters in cellular uptake of 4'-thio-beta-D-arabinofuranosylcytosine and beta-D- arabinosylcytosine. Mol Pharmacol. 2006 Jul;70(1):303-10. doi: 10.1124/mol.105.021543. Epub 2006 Apr 14. PMID: 16617163. 12: Colagiovanni DB, Drolet DW, Dihel L, Meyer DJ, Hart K, Wolf J. Safety assessment of 4'-thio-beta-D-arabinofuranosylcytosine in the beagle dog suggests a drug-induced centrally mediated effect on the hypothalamic-pituitary-adrenal axis. Int J Toxicol. 2006 Mar-Apr;25(2):119-26. doi: 10.1080/10915810600605898. PMID: 16597550. 13: Goss G, Siu LL, Gauthier I, Chen EX, Oza AM, Goel R, Maroun J, Powers J, Walsh W, Maclean M, Drolet DW, Rusk J, Seymour LK; Investigational New Drug Program of the National Cancer Institute of Canada Clinical Trials Group. 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. Cancer Chemother Pharmacol. 2006 Nov;58(5):703-10. doi: 10.1007/s00280-006-0201-1. Epub 2006 Mar 10. PMID: 16528532. 14: Thottassery JV, Westbrook L, Someya H, Parker WB. c-Abl-independent p73 stabilization during gemcitabine- or 4'-thio-beta-D-arabinofuranosylcytosine- induced apoptosis in wild-type and p53-null colorectal cancer cells. Mol Cancer Ther. 2006 Feb;5(2):400-10. doi: 10.1158/1535-7163.MCT-05-0409. PMID: 16505115. 15: Someya H, Waud WR, Parker WB. Long intracellular retention of 4'-thio- arabinofuranosylcytosine 5'-triphosphate as a critical factor for the anti-solid tumor activity of 4'-thio-arabinofuranosylcytosine. Cancer Chemother Pharmacol. 2006 Jun;57(6):772-80. doi: 10.1007/s00280-005-0126-0. Epub 2005 Sep 23. PMID: 16180016. 16: Richardson F, Black C, Richardson K, Franks A, Wells E, Karimi S, Sennello G, Hart K, Meyer D, Emerson D, Brown E, LeRay J, Nilsson C, Tomkinson B, Bendele R. Incorporation of OSI-7836 into DNA of Calu-6 and H460 xenograft tumors. Cancer Chemother Pharmacol. 2005 Mar;55(3):213-21. doi: 10.1007/s00280-004-0844-8. Epub 2004 Nov 16. PMID: 15592840. 17: Richardson KA, Vega TP, Richardson FC, Moore CL, Rohloff JC, Tomkinson B, Bendele RA, Kuchta RD. Polymerization of the triphosphates of AraC, 2',2'-difluorodeoxycytidine (dFdC) and OSI-7836 (T-araC) by human DNA polymerase alpha and DNA primase. Biochem Pharmacol. 2004 Dec 15;68(12):2337-46. doi: 10.1016/j.bcp.2004.07.042. PMID: 15548380. 18: Waud WR, Gilbert KS, Shepherd RV, Montgomery JA, Secrist JA 3rd. Preclinical antitumor activity of 4'-thio-beta-D-arabinofuranosylcytosine (4'-thio-ara-C). Cancer Chemother Pharmacol. 2003 May;51(5):422-6. doi: 10.1007/s00280-003-0589-9. Epub 2003 Apr 1. PMID: 12679884. 19: Someya H, Shaddix SC, Tiwari KN, Secrist JA 3rd, Parker WB. Phosphorylation of 4'-thio-beta-D-arabinofuranosylcytosine and its analogs by human deoxycytidine kinase. J Pharmacol Exp Ther. 2003 Mar;304(3):1314-22. doi: 10.1124/jpet.102.045435. PMID: 12604712. 20: Tiwari KN, Shortnacy-Fowler AT, Cappellacci L, Waud WR, Parker WB, Montgomery JA, Secrist JA 3rd. Synthesis and structure activity relationships of 5-substituted-4'-thio-beta-D-arabinofuranosylcytosines. Nucleosides Nucleotides Nucleic Acids. 2000 Oct-Dec;19(10-12):2005-17. doi: 10.1080/15257770008045474. PMID: 11200287.