Active Ingredient History

  • Now
Tacrolimus, previously known as FK506, is the active ingredient in Prograf. Tacrolimus is a macrolide immunosuppressant produced by Streptomyces tsukubaensis. It reduces peptidyl-prolyl isomerase activity by binding to the immunophilin FKBP-12 (FK506 binding protein) creating a new complex. This FKBP12-FK506 complex interacts with and inhibits calcineurin thus inhibiting both T-lymphocyte signal transduction and IL-2 transcription. Tacrolimus inhibits T-lymphocyte activation, although the exact mechanism of action is not known. Experimental evidence suggests that tacrolimus binds to an intracellular protein, FKBP-12. A complex of tacrolimus-FKBP-12, calcium, calmodulin, and calcineurin is then formed and the phosphatase activity of calcineurin inhibited. This effect may prevent the dephosphorylation and translocation of nuclear factor of activated T-cells (NF-AT), a nuclear component thought to initiate gene transcription for the formation of lymphokines (such as interleukin-2, gamma interferon). The net result is the inhibition of T-lymphocyte activation (i.e., immunosuppression). Prograf is indicated for the prophylaxis of organ rejection in patients receiving allogeneic liver transplants, kidney transplants, heart transplants. It has also been used in a topical preparation in the treatment of severe atopic dermatitis.   NCATS

  • SMILES: CC[C@H](C(=O)N1CCCC[C@H]1C(=O)O[C@H](CCc2ccc(OC)c(OC)c2)c3cccc(OCC(=O)NCCNC(=O)COc4cccc(c4)[C@@H](CCc5ccc(OC)c(OC)c5)OC(=O)[C@@H]6CCCCN6C(=O)[C@@H](CC)c7cc(OC)c(OC)c(OC)c7)c3)c8cc(OC)c(OC)c(OC)c8
  • Mol. Mass: 1411.65
  • ALogP: 4.64
  • ChEMBL Molecules:
More Chemistry

Drug Pricing (per unit)

United States

$0.0953 - $113.3110


$0.9145 - $10.4262
More Pricing Detail

Note: This drug pricing data is preliminary, incomplete, and may contain errors.

2-piperidinecarboxylic acid, 1-((2s)-1-oxo-2-(3,4,5-trimethoxyphenyl)butyl)-, 2,2'-(1,2-ethanediylbis(imino(2-oxo-2,1-ethanediyl)oxy-3,1-phenylene((1r)-3-(3,4-dimethoxyphenyl)propylidene))) ester, (2s,2's)- | 417 | ac vax | adoport | advagraf | anhydrous tacrolimus | ap1903 | ap 1903 reagent | capexion | envarsus | fk506 | fk-506 | fr900506 | fr-900506 | fujimycin | modigraf | perixis | prograf | protopic | rimiducid | tacni | tacrolimus | tacrolimus anhydrous | tacrolimus, anhydrous | tacrolimus hydrate | tacrolimus monohydrate | tsukubaenolide | vivadex


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