WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 201590
CAS#: 198832-38-1 (hydrate)
Description: Isatoribine (also known as immunosine, or 7-thia-8-oxoguanosine) is a novel guanosine analogue showing immunostimulatory activity both in vivo and in vitro. This compound acts on different components of the immune system including B cells, natural killer (NK) cells and antigen-presenting cells (APC). It was found that immunosine significantly stimulates proliferation of T cells. The effect was dose-dependent and also depended on concentrations of specific stimulators. Maximal stimulation was seen using 250 microM immunosine.
MedKoo Cat#: 201590
Name: Isatoribine hydrate
CAS#: 198832-38-1 (hydrate)
Chemical Formula: C10H14N4O7S
Exact Mass: 316.04775
Molecular Weight: 334.31
Elemental Analysis: C, 35.93; H, 4.22; N, 16.76; O, 33.50; S, 9.59
This product is not in stock, which may be available by custom synthesis.
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Synonym: ANA245; ANA-245; ANA 245; Immusine; Isatoribine hydrate; Isatoribine monohydrate; D04619; 7-thia-8-oxoguanosine.
IUPAC/Chemical Name: 5-amino-3-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione hydrate
InChi Key: BZWQQOVSUSJJJO-QAGDRQIHSA-N
InChi Code: InChI=1S/C10H12N4O6S.H2O/c11-9-12-6-5(7(18)13-9)21-10(19)14(6)8-4(17)3(16)2(1-15)20-8;/h2-4,8,15-17H,1H2,(H3,11,12,13,18);1H2/t2-,3-,4-,8-;/m1./s1
SMILES Code: O=C(N1[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)SC3=C1N=C(N)NC3=O.[H]O[H]
Appearance: Solid powder
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
The following data is based on the product molecular weight 334.31 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.
|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: Xiang AX, Webber SE, Kerr BM, Rueden EJ, Lennox JR, Haley GJ, Wang T, Ng JS, Herbert MR, Clark DL, Banh VN, Li W, Fletcher SP, Steffy KR, Bartkowski DM, Kirkovsky LI, Bauman LA, Averett DR. Discovery of ANA975: an oral prodrug of the TLR-7 agonist isatoribine. Nucleosides Nucleotides Nucleic Acids. 2007;26(6-7):635-40. PubMed PMID: 18066870.
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7: Colić M, Jandrić D, Gasić S, Vucević D, Popović P, Medić-Mijacević L, Rakić L. Immunosine (7-thia-8-oxoguanosine) acts as a cofactor for proliferation of T cells. Fundam Clin Pharmacol. 2000 May-Jun;14(3):209-17. PubMed PMID: 15602797.
8: Lee J, Chuang TH, Redecke V, She L, Pitha PM, Carson DA, Raz E, Cottam HB. Molecular basis for the immunostimulatory activity of guanine nucleoside analogs: activation of Toll-like receptor 7. Proc Natl Acad Sci U S A. 2003 May 27;100(11):6646-51. Epub 2003 May 8. PubMed PMID: 12738885; PubMed Central PMCID: PMC164501.
9: Colić M, Gasić S, Vucević D, Pavicić L, Popović P, Jandrić D, Medić-Mijacević L, Rakić L. Modulatory effect of 7-thia-8-oxoguanosine on proliferation of rat thymocytes in vitro stimulated with concanavalin A. Int J Immunopharmacol. 2000 Mar;22(3):203-12. PubMed PMID: 10685003.
10: Colic M, Vucevic D, Vasilijic S, Popovic L, Pejanovic V, Jandric D, Medic-Mijacevic L, Rakic L. Proliferation of spleen cells in culture stimulated by 7-thia-8-oxoguanosine: evidence that both B- and T-cells are the targets of its action. Methods Find Exp Clin Pharmacol. 1999 Nov;21(9):583-90. PubMed PMID: 10669901.
11: Colić M, Gasić S, Vasilijić S, Pejanović V, Jandrić D, Medić-Mijacević L, Rakić L. A nucleoside analogue, 7-thia-8-oxoguanosine stimulates proliferation of thymocytes in vitro. Immunol Lett. 1999 Sep 1;69(3):293-300. PubMed PMID: 10528791.
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17: Sharma BS, Mhaskar S, Balazs L, Siaw M. Immunomodulatory activity of a novel nucleoside, 7-thia-8-oxoguanosine: I. Activation of natural killer cells in mice. Immunopharmacol Immunotoxicol. 1992;14(1-2):1-19. PubMed PMID: 1597650.
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19: Kini GD, Anderson JD, Sanghvi YS, Lewis AF, Smee DF, Revankar GR, Robins RK, Cottam HB. Synthesis and antiviral activity of certain guanosine analogues in the thiazolo[4,5-d]pyrimidine ring system. J Med Chem. 1991 Oct;34(10):3006-10. PubMed PMID: 1656042.
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Isatoribine is currently developed by Anadys Pharmaceuticals, Inc. According to Anadys's website, is atoribine is a nucleoside analog currently in evaluating in ongoing clinical trials for the treatment of HCV infections. Isatoribine represents one of a new class of drugs being developed by Anadys to regulate innate immunity, combat HCV infection, and overcome limitations of current anti-HCV therapies. Anadys believes isatoribine interacts with a specific receptor, Toll-like receptor 7, or TLR7, that is present on certain immune system cells. Although results of initial clinical trials may not be predictive of future results, interim results of the Phase 1B clinical trial show that isatoribine is biologically active in adults with chronic HCV infection and results from dosing a cohort of six HCV infected patients with 800mg of isatoribine showed a statistically significant reduction of viral load (p=0.03) at the end of one week, with a median change in viral load from baseline of -0.94 log10 units. Anadys is currently enrolling patients for an isatoribine Phase I/II study.
Current developer: Anadys Pharmaceuticals, Inc .