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FK-506

Cayman Chemical Item Number 10007965

Tacrolimus (CAS 104987-11-3)

FK-506 (CAS 104987-11-3)

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Description

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+.

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

2 Dumont, F.J. FK506, An immunosuppressant targeting calcineurin function. Curr Med Chem 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 21-26 (1998).

Synonyms
  • Tacrolimus
Formal Name 5,​6,​8,​11,​12,​13,​14,​15,​16,​17,​18,​19,​24,​25,​26,​26aS-​hexahydro-​5S,​19R-​dihydroxy-​3S-​[(1E)-​2-​(4R-​hydroxy-​3R-​methoxycyclohexyl)-​1R-​methylethenyl]-​14S,​16S-​dimethoxy-​4R,​10,​12S,​18R-​tetramethyl-​8R-​(2-​propenyl)-​15R,​19R-​epoxy-​3H-​pyrido[2,​1-​c][1,​4]oxazacyclotrisosine-​1,​7,​20,​21,​(4H,​23H)-​tetrone
CAS Number 104987-11-3
Molecular Formula C44H69NO12
Formula Weight 804.0
Formulation A crystalline solid
Purity ≥99%
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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CO[C@H]​1C[C@@H]​(C)​[C@@]​(C(C(N2[C@H]​(C(O[C@@H]​([C@H]​(C)​[C@@H]​(O)​C3)​/C(C)​=C/[C@@H]​4CC[C@@H]​(O)​[C@H]​(OC)​C4)​=O)​CCCC2)​=O)​=O)​(O)​O[C@@H]​1[C@@H]​(OC)​C[C@H]​(C)​C/C(C)​=C/[C@@H]​(CC=C)​C3=O

Background Reading

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

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

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

FK-506 is available in the following screening library:

Size Price Quantity Subtotal
5 mg $28.00 $0.00
10 mg $53.00 $0.00
50 mg $224.00 $0.00
100 mg $392.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-26. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

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