F4679

FK-506 monohydrate

≥98% (HPLC)

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

Properties

• Quality Level: 100
• 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

Packaging

5 mg in glass bottle

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.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301
• Precautionary Statements: P301 + P310
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class Code: 6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves