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FK-506
Cayman Chemical Item Number 10007965
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+.
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 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
InCHI Code 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
InCHI Key QJJXYPPXXYFBGM-DRNMLEGNSA-N |