Isatoribine

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

MedKoo CAT#: 201590

CAS#: 198832-38-1

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. The stimulatory effect of immunosine on lymphocyte proliferation triggered by Concanavalin A (Con A) correlated with increased interleukin 2 (IL-2) production and upregulation of the IL-2 receptor alpha (IL-2Ralpha) expression. (source: Fundam Clin Pharmacol. 2000 May-Jun;14(3):209-17.)


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Isatoribine is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 201590
Name: Isatoribine
CAS#: 198832-38-1
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


Synonym: ANA245;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]


Technical Data

Appearance:
Solid powder

Purity:
>98%

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).

Harmonized System Code:
293490


Additional Information

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 .
 
 


References

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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.

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14: Lewis AF, Drach JC, Fennewald SM, Huffman JH, Ptak RG, Sommadossi JP, Revankar GR, Rando RF. Inhibition of human cytomegalovirus in culture by alkenyl guanine analogs of the thiazolo[4,5-d]pyrimidine ring system. Antimicrob Agents Chemother. 1994 Dec;38(12):2889-95. PubMed PMID: 7695278; PubMed Central PMCID: PMC188302.

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24: Girgis NS, Michael MA, Smee DF, Alaghamandan HA, Robins RK, Cottam HB. Direct C-glycosylation of guanine analogues: the synthesis and antiviral activity of certain 7- and 9-deazaguanine C-nucleosides. J Med Chem. 1990 Oct;33(10):2750-5. PubMed PMID: 2170645.

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