MilliporeSigma
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F4679

Sigma-Aldrich

FK-506 monohydrate

≥98% (HPLC)

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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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.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

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

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

Product Information Sheet

More Documents

Quotes and Ordering

Reversible Cyclosporin A-sensitive Mitochondrial Depolarization Occurs within Minutes of Stroke Onset in Mouse Somatosensory Cortex in Vivo A TWO-PHOTON IMAGING STUDY
Liu RR and Murphy TH
Test, 284(52), 36109-36117 (2009)
Neuroregenerative and neuroprotective actions of neuroimmunophilin compounds in traumatic and inflammatory neuropathies
Gold Bruce G, et al.
Neurological Research, 26(4), 371-380 (2004)
Xenografted Human Amniotic Membrane-Derived Mesenchymal Stem Cells Acquired Immune Tolerance and Transdifferentiated Into Cardiomyocytes in Vivo
Tsuji H, et al.
Circulation Research, 1613?1623-1613?1623 (2008)
FK506, an immunosuppressant targeting calcineurin function
Dumont FJ
Current Medicinal Chemistry, 7(7), 731-748 (2000)
Transforming growth factor beta-related genes in human retinal pigment epithelial cells after tacrolimus treatment
Kimsa M, et al.
Pharmacological Reports, 68(5), 969-974 (2016)

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