F4679

FK-506 monohydrate

≥98% (HPLC), powder, in vitro T cell proliferation blocker

• Synonym(s): Tacrolimus
• Empirical Formula (Hill Notation): C₄₄H₆₉NO₁₂ · H₂O
• CAS Number: 109581-93-3
• Molecular Weight: 822.03
• MDL number: MFCD11045918
• UNSPSC Code: 12352200
• PubChem Substance ID: 24724482
• NACRES: NA.77

Properties

• product name: FK-506 monohydrate, ≥98% (HPLC)
• assay: ≥98% (HPLC)
• form: powder
• solubility: DMSO: 20 mg/mL
• storage temp.: −20°C
• SMILES string: O.CO[C@@H]1C[C@@H](CC[C@H]1O)\C=C(/C)[C@H]2OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@]4(O)O[C@H]([C@H](C[C@@H](C)C\C(C)=C\[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)OC)[C@H](C[C@H]4C)OC
• InChI: 1S/C44H69NO12.H2O/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,1,11-18,20,22-24H2,2-9H3;1H2/b25-19+,27-21+;/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+;/m0./s1
• InChI key: NWJQLQGQZSIBAF-MLAUYUEBSA-N
• Gene Information: human ... FKBP1A(2280)

Description

Application

FK-506 monohydrate has been used:

• as an immunosuppressive agent in coculture medium to study the effect of immunologic reaction
• as a calcineurin inhibitor, in anhydrous Me₂SO solution
• to treat retinal pigment epithelial cells to measure possible cytotoxicity

Biochem/physiol Actions

FK-506 also appears to inhibit Na⁺/Ca²⁺ exchange. FK-506 and its derivatives demonstrate significant neurodegenerative activity. This property seems to arise via different mechanisms. FK-506 is also useful in treating ophthalmologic complications such as corneal graft rejection, uveoretinitis and allergen induced conjunctivitis.

FK-506 is a potent immunosuppressant, neuroprotective and neuroregenerative, and in vitro T cell proliferation blocker. FK-506 disrupts calcineurin-mediated signal transduction in T lymphocytes and interacts with its FK-506-binding protein-12 (FKBP12).

Features and Benefits

This compound is a featured product for ADME Tox and Neuroscience research. Discover more featured ADME Tox and Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Phosphoprotein Phosphatases (Serine/Threonine) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301
• pcodes: P301 + P310
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges