FK506 (Tacrolimus)
Molecular Formula
C44H69NO12
M.W.
804.02
CAS number
104987-11-3
Source
Streptomyces tsukubaensis
Fermentek product Code
FK5-001
Brand/grade
For research
Appearance
White powder
Purity by HPLC
≥98% ; refer to CoA for more data
Purity By TLC
≥98% ; refer to CoA for more data
Melting point
125°C-132°C
Solubility test
Clear colorless solution at 10 mg/ml Ethyl Acetate or DMSO
Names and identifiers

Synonyms: FK506, Tacrolimus,

RTECS:       KD4200000

EU number
658-056-2
Chemical name
FK506
Description

FK506 is 23-membered macrolide lactone discovered in 1984, by Kino T, Hatanaka H and Hashimoto M. [reference 2] FK506 exhibits potent inhibitory effect on T- lymphocyte activation. It binds to immunophilins FK506 binding proteins (FKBP-12) and a complex of FKBP-12, calcium, calmodulin and calcineurin is formed, inhibiting phosphatase activity of calcineurin. This prevents dephosphorylation and translocation of nuclear factor of activated T – cells (NF-AT) and inhibits transcription of early T-cell activation gene, Interleukin-2, Tumour Necrosis Factor (TNF-a) and proto-oncogenes; suppressing expression of IL-2 and IL-7 receptor. This results in inhibition of T-lymphocyte activation. FK506 also inhibits the mixed lymphocyte reaction, generation of cytotoxic T-cells and T-cell dependent B-cell activation.

InChl Key
QJJXYPPXXYFBGM-LFZNUXCKSA-N
Canonical SMILES
CC1CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC(=O)C(C=C(C1)C)CC=C)O)C)C(=CC4CCC(C(C4)OC)O)C)O)C)OC)OC
Isomeric SMILES
C[C@@H]1C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC(=O)[C@@H](/C=C(/C1)\C)CC=C)O)C)/C(=C/[C@@H]4CC[C@H]([C@@H](C4)OC)O)/C)O)C)OC)OC
Solubility ( literature )

FK506 is soluble in Methanol, Ethanol, Acetone, Ethyl Acetate, Diethyl ether, Chloroform, Dicloromethane. FK506 is sparingly soluble in Hexane, Petroleum ether. FK506 is insoluble in water

Compound Classification

Chemical classification:

Macrolide

Bioactivity classification

Immunosuppressant

Storage, handling
Store in a freezer upon arrival, at -10°C to -25°C
Protect from moisture
Applications

FK506 (Tacrolimus) is used as an immunosuppressant at organ transplantations. For experimental uses of FK506 (Tacrolimus) read also United States Patent Application 20090098200

Disclaimer
For Research use only
Not for Human or Drug use
Not extracted from humans or animals
Refer to MSDS for further safety and handling instructions
Ingredient type
Fermentek product
Title
toxicity by RTECS
Value
>200mg/kg oral mouse
Fermentek Product Category
Signal to sort
F