An internal standard for the quantification of FK-506
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Unlabeled Version(s)
10007965FK-506
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FK-506-13C-d2

Item No. 22178

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
1356841-89-8
Synonyms
  • Tacrolimus-13C-d2
Molecular Formula
C43[13C]H67D2NO12
Formula Weight
807.0
Purity
≥98% deuterated forms (d1-d2); ≤2% d0
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: Slightly SolubleMethanol: Slightly Soluble
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]3C/C=[13C]([2H])\[2H])=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/i1+1D2
InChi Key
QJJXYPPXXYFBGM-QNEHJXMKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $688

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    Product Description

    FK-506-13C-d2 contains two deuterium atoms located on the carbon-13 bond. It is intended for use as an internal standard for the quantification of FK-506 (Item No. 10007965) by GC- or LC-MS. FK-506 is a potent, clinically-useful immunosuppressant in the same molecular class as cyclosporin A and rapamycin.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).