Isatoribine hydrate

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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.

Chemical Structure

Isatoribine hydrate
CAS# 198832-38-1 (hydrate)

Theoretical Analysis

MedKoo Cat#: 201590
Name: Isatoribine hydrate
CAS#: 198832-38-1 (hydrate)
Chemical Formula: C10H14N4O7S
Exact Mass: 316.05
Molecular Weight: 334.310
Elemental Analysis: C, 35.93; H, 4.22; N, 16.76; O, 33.50; S, 9.59

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales or click below button.
Note: Price will be listed if it is available in the future.

Related CAS #: 198832-38-1 (hydrate), 122970-40-5 (free base),

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 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

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).

HS Tariff Code: 2934.99.9001

Product Data:

Preparing Stock Solutions

The following data is based on the product molecular weight 334.310000000000000000000000000000 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.

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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: 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. 2: Jin G, Wu CC, Carson DA, Cottam HB. Guanosine analog in the pyrido[2,3-d]pyrimidine ring system as a potential toll-like receptor agonist. Nucleosides Nucleotides Nucleic Acids. 2006;25(12):1391-7. PubMed PMID: 17067960. 3: Fletcher S, Steffy K, Averett D. Masked oral prodrugs of toll-like receptor 7 agonists: a new approach for the treatment of infectious disease. Curr Opin Investig Drugs. 2006 Aug;7(8):702-8. Review. PubMed PMID: 16955681. 4: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Nov;27(9):665-77. PubMed PMID: 16357953. 5: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2005 Oct;27(8):569-612. PubMed PMID: 16273137. 6: Horsmans Y, Berg T, Desager JP, Mueller T, Schott E, Fletcher SP, Steffy KR, Bauman LA, Kerr BM, Averett DR. Isatoribine, an agonist of TLR7, reduces plasma virus concentration in chronic hepatitis C infection. Hepatology. 2005 Sep;42(3):724-31. PubMed PMID: 16116638. 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. 12: Black PL, McKinnon KM, Wooden SL, Ussery MA. Antiviral activity of biological response modifiers in a murine model of AIDS. Requirement for augmentation of natural killer cell activity and synergy with oral AZT. Int J Immunopharmacol. 1996 Nov;18(11):633-50. PubMed PMID: 9089007. 13: Smee DF, Alaghamandan HA, Ramasamy K, Revankar GR. Broad-spectrum activity of 8-chloro-7-deazaguanosine against RNA virus infections in mice and rats. Antiviral Res. 1995 Mar;26(2):203-9. PubMed PMID: 7605116. 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. 15: Sidwell RW, Huffman JH, Barnard DL, Smee DF, Warren RP, Chirigos MA, Kende M, Huggins J. Antiviral and immunomodulating inhibitors of experimentally-induced Punta Toro virus infections. Antiviral Res. 1994 Oct;25(2):105-22. PubMed PMID: 7847873. 16: Sidwell RW, Huffman JH, Smee DF, Gilbert J, Gessaman A, Pease A, Warren RP, Huggins J, Kende M. Potential role of immunomodulators for treatment of phlebovirus infections of animals. Ann N Y Acad Sci. 1992 Jun 16;653:344-55. PubMed PMID: 1385686. 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. 18: Sharma BS, Mhaskar S, Balazs L, Jin A, Smee DF. Immunomodulatory activity of a novel nucleoside, 7-thia-8-oxoguanosine. II. Characterization of induced effector cells and the mechanism of induction. Immunopharmacol Immunotoxicol. 1992;14(1-2):21-38. PubMed PMID: 1375956. 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. 20: Sharma BS, Balazs L, Jin A, Jolley WB, Robins RK. Successful immunotherapy of murine melanoma metastases with 7-thia-8-oxoguanosine. Clin Exp Metastasis. 1991 Sep-Oct;9(5):429-39. PubMed PMID: 1914279. 21: Smee DF, Huffman JH, Gessaman AC, Huggins JW, Sidwell RW. Prophylactic and therapeutic activities of 7-thia-8-oxoguanosine against Punta Toro virus infections in mice. Antiviral Res. 1991 Mar-Apr;15(3):229-39. PubMed PMID: 1716090. 22: Sharma BS, Balazs L, Jin A, Wang JC, Jolley WB, Robins RK. Potentiation of the efficacy of murine L1210 leukemia vaccine by a novel immunostimulator 7-thia-8-oxoguanosine: increased survival after immunization with vaccine plus 7-thia-8-oxoguanosine. Cancer Immunol Immunother. 1991;33(2):109-14. PubMed PMID: 2036658. 23: Smee DF, Alaghamandan HA, Gilbert J, Burger RA, Jin A, Sharma BS, Ramasamy K, Revankar GR, Cottam HB, Jolley WB, et al. Immunoenhancing properties and antiviral activity of 7-deazaguanosine in mice. Antimicrob Agents Chemother. 1991 Jan;35(1):152-7. PubMed PMID: 1707603; PubMed Central PMCID: PMC244957. 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. 25: Bontems RJ, Anderson JD, Smee DF, Jin A, Alaghamandan HA, Sharma BS, Jolley WB, Robins RK, Cottam HB. Guanosine analogues. Synthesis of nucleosides of certain 3-substituted 6-aminopyrazolo[3,4-d]pyrimidin-4(5H)-ones as potential immunotherapeutic agents. J Med Chem. 1990 Aug;33(8):2174-8. PubMed PMID: 2165164. 26: Jin A, Mhaskar S, Jolley WB, Robins RK, Ojo-Amaize EA. A novel guanosine analog, 7-thia-8-oxoguanosine, enhances macrophage and lymphocyte antibody-dependent cell-mediated cytotoxicity. Cell Immunol. 1990 Apr 1;126(2):414-9. PubMed PMID: 2311125. 27: Smee DF, Alaghamandan HA, Cottam HB, Jolley WB, Robins RK. Antiviral activity of the novel immune modulator 7-thia-8-oxoguanosine. J Biol Response Mod. 1990 Feb;9(1):24-32. PubMed PMID: 2156954. 28: Smee DF, Alaghamandan HA, Jin A, Sharma BS, Jolley WB. Roles of interferon and natural killer cells in the antiviral activity of 7-thia-8-oxoguanosine against Semliki Forest virus infections in mice. Antiviral Res. 1990 Feb;13(2):91-102. PubMed PMID: 1693058. 29: Ojo-Amaize EA, Rubalcava B, Avery TL, Cottam HB, Matsumoto SS, Jolley WB, Robins RK. Activation of the respiratory burst in murine phagocytes by certain guanine ribonucleosides modified at the 7 and 8 positions: possible involvement of a pertussis toxin-sensitive G-protein. Immunol Lett. 1990 Jan;23(3):173-8. PubMed PMID: 2106487. 30: Parandoosh Z, Ojo-Amaize E, Robins RK, Jolley WB, Rubalcava B. Stimulation of phosphoinositide signaling pathway in murine B lymphocytes by a novel guanosine analog, 7-thia-8-oxoguanosine. Biochem Biophys Res Commun. 1989 Sep 29;163(3):1306-11. PubMed PMID: 2551285. 31: Smee DF, Alaghamandan HA, Cottam HB, Sharma BS, Jolley WB, Robins RK. Broad-spectrum in vivo antiviral activity of 7-thia-8-oxoguanosine, a novel immunopotentiating agent. Antimicrob Agents Chemother. 1989 Sep;33(9):1487-92. PubMed PMID: 2817849; PubMed Central PMCID: PMC172688. 32: Robins RK, Ojo-Amaize E, Parandoosh Z, Cottam HB, Matsumoto SS, Revankar GR, Smee DF, Fujitaki JM, Willis RC, Rubalcava B, et al. Nucleoside and nucleotide modulation of genetic expression--a new approach to chemotherapy. Adv Enzyme Regul. 1989;29:97-121. PubMed PMID: 2517379.