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ProductsBack/FK-506 [Tacrolimus]
Chemical Structure
Chemical Structure
Chemical Structure

FK-506 [Tacrolimus]

Research Use Only
AG-CN2-0047
AdipoGen Life Sciences
CAS Number109581-93-3
DownloadMSDS
Product group Chemicals
Estimated Purity>98%
Molecular Weight804.0 . 18.0
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    FK-506 [109581-93-3]
  • Delivery Days Customer
    10
  • ADR Class
    6.1
  • CAS Number
    109581-93-3
  • Certification
    Research Use Only
  • Estimated Purity
    >98%
  • Hazard Information
    Danger,Excepted quantity
  • Molecular Formula
    C44H69NO12 . H2O
  • Molecular Weight
    804.0 . 18.0
  • Scientific Description
    Chemical. CAS: 109581-93-3. Formula: C44H69NO12 . H2O. MW: 804.0 . 18.0. Isolated from Streptomyces FCZ0311. Potent immunosuppressant (as cyclosporin A and rapamycin). Suppresses proliferation of cytotoxic T cells and inhibits the production of T cell-derived mediators such as interleukin-2 (IL-2). Forms a complex with FK-506 binding protein 12 (FKBP12). Inhibits the activity of the calcium/calmodulin-dependent protein phosphatase 2B (PP2B; calcineurin), leading to disruption of T cell activation. Prevents rejection of transplanted organs. Anti-inflammatory compound in the treatment of several inflammatory skin diseases (e.g. atopic dermatitis) and with potential anti-rheumatic activity (rheumatoid arthritis). Neuroprotective. Regulates nitric oxide neurotoxicity. Neurotransmitter. Ca2+ release compound. NF-kappaB suppressor by induction of unfolded protein response (UPR). Anti-cancer compound. Apoptosis inducer. - Potent immunosuppressant (as cyclosporin A and rapamycin) [1-3]. Suppresses proliferation of cytotoxic T cells and inhibits the production of T cell-derived mediators such as interleukin-2 (IL-2) [2, 4]. Forms a complex with FK-506 binding protein 12 (FKBP12). Inhibits the activity of the calcium/calmodulin-dependent protein phosphatase 2B (PP2B; calcineurin), leading to disruption of T cell activation [2, 4, 6, 7]. Prevents rejection of transplanted organs [3]. Anti-inflammatory compound in the treatment of several inflammatory skin diseases (e.g. atopic dermatitis) and with potential anti-rheumatic activity (rheumatoid arthritis) [5, 9]. Neuroprotective. Regulates nitric oxide neurotoxicity. Neurotransmitter. Ca2+ release compound [8]. NF-kappaB suppressor by induction of unfolded protein response (UPR) [11]. Anti-cancer compound. Apoptosis inducer [10, 12].
  • SMILES
    [H]O[H].[H][C@]1(CC[C@@]([H])(O)[C@@]([H])(C1)OC)\C=C(/C)[C@@]1([H])OC(=O)C2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@]([H])([C@H](C[C@@]2([H])C)OC)[C@]([H])(C[C@@]([H])(C)C\C(C)=C\[C@@]([H])(CC=C)C(=O)CC(O)[C@@]1([H])C)OC
  • Storage Instruction
    -20°C,2°C to 8°C
  • UN Number
    UN 2811
  • UNSPSC
    12352200

References

  • FK-506, a novel immunosuppressant isolated from a Streptomyces. I. Fermentation, isolation, and physico-chemical and biological characteristics: T. Kino, et al.; J. Antibiot. (Tokyo) 40, 1249 (1987)
  • Cyclosporin A, FK506 and rapamycin: more than just immunosuppression: J. Kunz & M.N. Hall; TIBS 18, 334 (1993)
  • Cyclosporin A and FK506: molecular mechanisms of immunosuppression and probes for transplantation biology: B.E. Bierer, et al.; Curr. Opin. Immunol. 5, 763 (1993)
  • The actions of cyclosporin A and FK506 on T-lymphocyte activation: P.S. Mattila; Biochem. Soc. Trans. 24, 45 (1996) (Review)
  • FK506 in the treatment of inflammatory skin disease: promises and perspectives: G. Michel, et al.; Immunol. Today 17, 106 (1996) (Review)
  • The mechanism of action of cyclosporin A and FK506: S. Ho, et al.; Clin. Immunol. Immunopathol. 80, S40 (1996) (Review)
  • FK506, an immunosuppressant targeting calcineurin function: F.J. Dumont; Curr. Med. Chem. 7, 731 (2000) (Review)
  • FK506 and its analogs - therapeutic potential for neurological disorders: A. Klettner & T. Herdegen; Curr. Drug Targets CNS Neurol. Disord. 2, 153 (2003) (Review)
  • A review of the action of tacrolimus (FK506) on experimental models of rheumatoid arthritis: S. Miyata, et al.; Inflamm. Res. 54, 1 (2005) (Review)
  • Metabolism of tacrolimus (FK506) and recent topics in clinical pharmacokinetics: K. Iwasaki; Drug Metab. Pharmacokinet. 22, 328 (2007) (Review)