FK-506, Tacrolimus

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FK-506, Tacrolimus

F-1030
  • CAS: 104987-11-3
  • Formula: C44H69NO12
  • MW: 804.0
  • Appearance: White powder
  • Purity: ≥99%

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TacrolimusFK-506 or Fujimycin is an immunosuppressive drug that is mainly used after allogeneic organ transplant to reduce the activity of the patient's immune system and so lower the risk of organ rejection. It is also used in a topical preparation in the treatment of atopic dermatitis (eczema), severe refractory uveitis after bone marrow transplants, and for the skin condition vitiligo.

Tacrolimus is a macrolide compound isolated from the bacterium Streptomyces tsukubaensis. In T-cells, activation of the T-cell receptor normally increases intracellular calcium, which acts via calmodulin to activate calcineurin. Calcineurin then dephosphorylates the transcription factor NF-AT (nuclear factor of activated T-cells), which moves to the nucleus of the T-cell and increases the activity of genes coding for IL-2 and related cytokines. Tacrolimus prevents the dephosphorylation of NF-AT. 

In detail, Tacrolimus reduces peptidyl-prolyl isomerase activity by binding to the immunophilin FKBP12 (FK506 binding protein) creating a new complex. This FKBP12-FK506 complex interacts with and inhibits calcineurin thus inhibiting both T-lymphotye signal transduction and IL-2 transcription. Although this activity is similar to cyclosporine, studies have shown that the incidence of acute rejection is reduced by tacrolimus use over cyclosporine.Although short-term immunosuppression concerning patient and graft survival is found to be similar between the two drugs, tacrolimus results in a more favorable lipid profile, and this may have important long-term implications given the prognostic influence of rejection on graft survival.

 

Additional Information

SynonymsTacrolimus, FR-900506, Prograf, Protopic, Fujimycin
Product #F-1030
CAS #104987-11-3
FormulaC44H69NO12
MW804.0
AppearanceWhite powder
Purity≥99%
SolubilitySoluble in DMSO (100mg/ml), dichloomethane, 100%
Melting Point130-132°C
Storage Temp-20°C, Store in Tightly Sealed Vial.
Therapeutic AreaImmunotherapy
UseImmunosuppressive agent following organ transplantation, dermatological use

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Merck Index13.9117.2001

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msds 1F-1030, FK-506, SDS, diamond format.pdf
Certificate of Analysis 1F-1030, G1212A.pdf
Certificate of Analysis 2F-1030, G1212.pdf
Certificate of Analysis 3F-1030, F1198E.pdf
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CitationsQiu, Yu, et al. "FK506-binding protein 12 modulates u-opioid receptor phosphorylation and protein kinase CE-dependent signaling by its direct interaction with the receptor." Molecular pharmacology 85.1 (2014): 37-49.
Sharp, Willard W., et al. "Dynamin-Related Protein 1 (Drp1)-Mediated Diastolic Dysfunction in Myocardial Ischemia-Reperfusion Injury: Therapeutic Benefits of Drp1 Inhibition to Reduce Mitochondrial Fission." The FASEB Journal, vol. 28, no. 1, 27 Sept. 2013, pp. 316-326., doi:10.1096/fj.12-226225.
Elmer, Bradford M., et al. "MHCI requires MEF2 transcription factors to negatively regulate synapse density during development and in disease." Journal of Neuroscience 33.34 (2013): 13791-13804.
Cokol, Murat, et al. "Systematic exploration of synergistic drug pairs." Molecular systems biology 7.1 (2011): 544.
Weber, Kassandra J., and Joel D. Schilling. "Lysosomes integrate metabolic-inflammatory crosstalk in primary macrophage inflammasome activation." Journal of Biological Chemistry (2014): jbc-M113.
Swartz, Douglas J., et al. "Directed evolution of P-glycoprotein cysteines reveals site-specific, non-conservative substitutions that preserve multidrug resistance." Bioscience reports 34.3 (2014): e00116.
Yan, Ying-Hui, et al. "Role of FK506 binding protein 12 in morphine-induced u-opioid receptor internalization and desensitization." Neuroscience letters 566 (2014): 231-235.
Singh-Babak, Sheena D., et al. "Global Analysis of the Evolution and Mechanism of Echinocandin Resistance in Candida Glabrata." PLoS Pathogens, vol. 8, no. 5, 17 May 2012, doi:10.1371/journal.ppat.1002718.\n
Velivela, Swetha Devi, and Patricia M. Kane. "Compensatory Internalization of Pma1 in V-ATPase Mutants in Saccharomyces cerevisiae Requires Calcium-and Glucose-Sensitive Phosphatases." Genetics 208.2 (2018): 655-672.
Mount, Harley O'Connor, et al. "Global analysis of genetic circuitry and adaptive mechanisms enabling resistance to the azole antifungal drugs." PLoS genetics 14.4 (2018): e1007319.
Frederick, Rebecca L., et al. "Yeast Miro GTPase, Gem1p, regulates mitochondrial morphology via a novel pathway." The Journal of cell biology 167.1 (2004): 87-98.
Saxena, Mansi, et al. "CpG Protects Human Monocytic Cells against HIV-Vpr-Induced Apoptosis by Cellular Inhibitor of Apoptosis-2 through the Calcium-Activated JNK Pathway in a TLR9-Independent Manner." The Journal of Immunology (2011): 1100115.
Prieto, G. Aleph, et al. "Upregulation of D2-class signaling in dopamine-denervated striatum is in part mediated by D3 receptors acting on CaV2. 1 channels via PIP2 depletion." Journal of neurophysiology 105.5 (2011): 2260-2274.
George, Andrew A., Gregory T. Macleod, and Harold H. Zakon. "Calcium-dependent phosphorylation regulates neuronal stability and plasticity in a highly precise pacemaker nucleus." Journal of neurophysiology 106.1 (2011): 319-331.
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