F4679

FK-506 monohydrate

Name: FK-506 monohydrate
Brand: SIGMA

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

Synonym(s):

Tacrolimus

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About This Item

Empirical Formula (Hill Notation):

C₄₄H₆₉NO₁₂ · H₂O

CAS Number:

109581-93-3

Molecular Weight:

822.03

UNSPSC Code:

12352200

PubChem Substance ID:

24724482

NACRES:

NA.77

MDL number:

MFCD11045918

Product Name

FK-506 monohydrate, ≥98% (HPLC)

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 key

NWJQLQGQZSIBAF-MLAUYUEBSA-N

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

assay

≥98% (HPLC)

form

powder

solubility

DMSO: 20 mg/mL

storage temp.

−20°C

Quality Level

100

Gene Information

human ... FKBP1A(2280)

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Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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).

FK-506 is a potent immunosuppressant; neuroprotective and neuroregenerative; in vitro T cell proliferation blocker.

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

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

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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Certificates of Analysis (COA)

Lot/Batch Number

0000467750

0000438434

0000371648

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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)

Neuroregenerative and neuroprotective actions of neuroimmunophilin compounds in traumatic and inflammatory neuropathies

Gold Bruce G, et al.

Neurological Research, 26(4), 371-380 (2004)

Lower variability in 24-hour exposure during once-daily compared to twice-daily tacrolimus formulation in kidney transplantation.

Frank Stifft et al.

Transplantation, 97(7), 775-780 (2014-04-02)

Tacrolimus has originally been registered as a twice-daily formulation (Prograf, Tac BID), although a once-daily formulation (Advagraf, Tac QD) is also available. A reduced intrapatient variability of Tac Cmin, a surrogate marker for 24-hour drug exposure (AUC0-24), has been suggested.

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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