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    Azathioprine (BW 57-322)
    Azathioprine (BW 57-322)

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    This product is for research use only, not for human use. We do not sell to patients.
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    InvivoChem Cat #: V1563
    CAS #: 446-86-6Purity ≥98%

    Description: Azathioprine (Azasan, Imuran; BW 57-322) is an approved immunosuppressive drug, inhibiting purine synthesis and GTP-binding protein Rac1 activation, it is used in the treatment of organ transplantation and autoimmune diseases. Azathioprine is a prodrug that has to be converted in vivo to its active metabolite 6-mercaptopurine (6-MP), which substitutes for the normal nucleoside and mistakenly gets incorporated into DNA sequences. This leads to inhibition of DNA, RNA, and protein synthesis. As a result, cell proliferation may be inhibited, particularly in lymphocytes and leukocytes. 

    References: J Clin Invest. 2003 Apr;111(8):1133-45; J Immunol. 2006 Jan 1;176(1):640-51; Exp Brain Res. 1995;106(2): 181-6.

    Related CAS: 97746-12-8 (Methazathioprine)

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    Molecular Weight (MW)277.26
    FormulaC9H7N7O2S
    CAS No.446-86-6
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 54 mg/mL (194.8 mM)
    Water: <1 mg/mL
    Ethanol: <1 mg/mL
    Solubility (In vivo)

    Chemical Name: 6-((1-methyl-4-nitro-1H-imidazol-5-yl)thio)-7H-purine

    InChi Key: LMEKQMALGUDUQG-UHFFFAOYSA-N

    InChi Code: InChI=1S/C9H7N7O2S/c1-15-4-14-7(16(17)18)9(15)19-8-5-6(11-2-10-5)12-3-13-8/h2-4H,1H3,(H,10,11,12,13)

    SMILES Code: O=[N+](C1=C(SC2=C3NC=NC3=NC=N2)N(C)C=N1)[O-]

    Synonyms

    BW-57-322; BW57-322; BW 57-322; BW 57 322; Azathioprine, trade name: Imuran; Azasan; Imurel. Abbreviations: AZA. AZTP.


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    In Vitro

    In vitro activity: Azathioprine suppresses the activation of Rac1 target genes such as mitogen-activated protein kinase kinase (MEK), NF-kappaB, and bcl-x(L), leading to a mitochondrial pathway of apoptosis in primary human CD4+ T lymphocytes. Azathioprine thus converts a costimulatory signal into an apoptotic signal by modulating Rac1 activity. Azathioprine-generated 6-Thio-GTP thus prevents the development of an effective immune response via blockade of Vav activity on Rac proteins. Azathioprine (1 mM) restores ATP levels and arrests cell injury, while culture in glucose-enriched media augments ATP levels and ameliorates cell death. Azathioprine reduces viability 5-34% at day 1 and 42-92% by day 4. Azathioprine decreases the viability of hepatocytes and induces the following events in primary culture of isolated rat hepatocytes: intracellular reduces glutathione (GSH) depletion, metabolic activity reduction, and lactate dehydrogenase release. Azathioprine effect on hepatocytes is associated with swelling and increased oxygen consumption of intact isolated rat liver mitochondria.

    In VivoAzathioprine combined with cyclosporin A and prednisolone has resulted in survival of 14 out of 15 grafts (93%), compared with 11 out of 14 (79%) in the group treated with cyclosporin A alone in mouse-rat brain xenograft.
    Animal modelMouse-rat brain xenograft
    Formulation & Dosage
    References

    J Clin Invest. 2003 Apr;111(8):1133-45; J Immunol. 2006 Jan 1;176(1):640-51; Exp Brain Res. 1995;106(2):181-6.


    These protocols are for reference only. InvivoChem does not independently validate these methods.

    Azathioprine

    Azathioprine and its metabolites suppress lamellipodia but not filopodia formation in primary CD4+ T lymphocytes. J Immunol. 2006 Jan 1;176(1):640-51.
     
     

    Azathioprine

    Azathioprine suppresses binding of Vav-1 to Rac1 but not RhoA. J Immunol. 2006 Jan 1;176(1):640-51.


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