FK-506

FK506 (Tacrolimus)

Molecular Formula

C44H69NO12

M.W.

804.02

CAS number

104987-11-3

Details

Source

Streptomyces tsukubaensis

Fermentek product Code

FK5-001

Brand/grade

For research

Specifications

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

Chemical identification

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

Further Information

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

Retest time

3 Years

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

Composition

Ingredient type

Fermentek product

Other Fields

Title

toxicity by RTECS

Value