A potent immunosuppressant/inhibitor of T cell activation
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Labeled Version(s)
22178FK-506-13C-d2
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FK-506

Item No. 10007965

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-8-(2-propen-1-yl)-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone
CAS Number
104987-11-3
Synonyms
  • Tacrolimus
Molecular Formula
C44H69NO12
Formula Weight
804.0
Purity
≥99%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 30 mg/mlEthanol:PBS (pH 7.2)(1:5): .15 mg/ml
SMILES
O=C([C@@](CCCC1)([H])N1C(C([C@@]2(O)[C@H](C)C[C@H](OC)[C@@](O2)([H])[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H]3CC=C)=O)=O)O[C@H](/C(C)=C/[C@H]4C[C@@H](OC)[C@H](O)CC4)[C@H](C)[C@@H](O)CC3=O
InChi Code
InChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+/m0/s1
InChi Key
QJJXYPPXXYFBGM-LFZNUXCKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    50 mg

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    100 mg

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    Product Description

    FK-506 is a potent immunosuppressant in the same molecular class as cyclosporin A (Item No. 12088) and rapamycin (Item No. 13346).1 Its mechanism of action involves the formation of a high affinity complex (Ki = 0.2 nM) with FK-506 binding protein 12 (FKBP12). This complex then inhibits the activity of the calcium/calmodulin-dependent protein phosphatase, calcineurin, leading to disruption of T cell activation.2 The physiological effects of FK-506 also include regulation of nitric oxide neurotoxicity, neurotransmitter release, and regulation of Ca2+ release via the ryanodine and inositol-(1,4,5)-trisphosphate (IP3) receptors.3 In the latter case, FKBP12 forms a tight complex with both ryanodine and IP3 receptors which can be disrupted by FK-506, thereby rendering the receptors leaky to Ca2+.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schreiber, S.L. Chemistry and biology of the immunophilins and their immunosuppressive ligands. Science 251(4991), 283-287 (1991).

    2. Dumont, F.J. FK506, An immunosuppressant targeting calcineurin function. Curr. Med. Chem. 7(7), 731-748 (2000).

    3. Snyder, S.H., Sabatini, D.M., Lai, M.M., et al. Neural actions of immunophilin ligands. Trends Pharmacol. Sci. 19(1), 21-26 (1998).