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Merck

F4679

FK-506 monohydrate

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

Sinónimos:

Tacrolimus

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About This Item

Fórmula empírica (notación de Hill):
C44H69NO12 · H2O
Número CAS:
109581-93-3
Peso molecular:
822.03
UNSPSC Code:
12352200
PubChem Substance ID:
24724482
NACRES:
NA.77
MDL number:
MFCD11045918

Nombre del producto

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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Categorías relacionadas

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

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Clase de almacenamiento

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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Certificados de análisis (COA)

Lot/Batch Number
0000467750
0000467750
0000438434
0000438434
0000371648

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Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

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)
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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