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F4679

Sigma-Aldrich

FK-506 monohydrate

≥98% (HPLC)

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Synonym(s):
Tacrolimus
Empirical Formula (Hill Notation):
C44H69NO12 · H2O
CAS Number:
Molecular Weight:
822.03
MDL number:
PubChem Substance ID:

Quality Level

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)

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This Item
1642802Y0001926PHR1809
FK-506 monohydrate ≥98% (HPLC)

F4679

FK-506 monohydrate

Tacrolimus United States Pharmacopeia (USP) Reference Standard

1642802

Tacrolimus

Tacrolimus monohydrate European Pharmacopoeia (EP) Reference Standard

Y0001926

Tacrolimus monohydrate

Tacrolimus Pharmaceutical Secondary Standard; Certified Reference Material

PHR1809

Tacrolimus

form

powder

form

-

form

-

form

powder

Quality Level

100

Quality Level

-

Quality Level

-

Quality Level

300

storage temp.

−20°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-10 to -25°C

solubility

DMSO: 20 mg/mL

solubility

-

solubility

-

solubility

-

Gene Information

human ... FKBP1A(2280)

Gene Information

human ... FKBP1A(2280)

Gene Information

human ... FKBP1A(2280)

Gene Information

human ... FKBP1A(2280)

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.

pictograms

Skull and crossbones

signalword

Danger

hcodes

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


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