FK-506

Specifications / Handling

More Information
Product Details
Synonyms	Tacrolimus; Fujimycin
Product Type	Chemical
Properties
Formula	C₄₄H₆₉NO₁₂ . H₂O
MW	804.0 . 18.0
Merck Index	14: 9025
CAS	109581-93-3
RTECS	KD4200000
Source/Host Chemicals	Isolated from Streptomyces tsukubaensis.
Purity Chemicals	≥98% (HPLC)
Appearance	White to off-white solid.
Solubility	Soluble in DMSO, ethanol, methanol, ethyl acetate or acetone. Insoluble in water.
Identity	Determined by ¹H-NMR.
InChi Key	NWJQLQGQZSIBAF-CBLXODBSSA-N
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
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

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-κB suppressor by induction of unfolded protein response (UPR) [11].
Anti-cancer compound. Apoptosis inducer [10, 12].

Product 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)
Suppression of NF-kappaB by cyclosporin A and tacrolimus (FK506) via induction of the C/EBP family: implication for unfolded protein response: S. Du, et al.; J. Immunol. 182, 7201 (2009)
FK506 binding proteins as targets in anticancer therapy: S. Romano, et al.; Anticancer Agents Med. Chem. 10, 651 (2010) (Review)

Call	+41 61 926 6040
Fax	+41 61 926 6049