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Merck

F4679

FK-506 monohydrate

≥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
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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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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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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

F4679-BULK: + F4679-VAR: + F4679-5MG:

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Certificates of Analysis (COA)

Lot/Batch Number
0000467750
0000467750
0000438434
0000438434
0000371648

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Neuroregenerative and neuroprotective actions of neuroimmunophilin compounds in traumatic and inflammatory neuropathies
Gold Bruce G, et al.
Neurological Research, 26(4), 371-380 (2004)
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)
FK506, an immunosuppressant targeting calcineurin function
Dumont FJ
Current Medicinal Chemistry, 7(7), 731-748 (2000)
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)
Rania Rabie et al.
Liver transplantation : official publication of the American Association for the Study of Liver Diseases and the International Liver Transplantation Society, 19(1), 36-48 (2012-07-24)
Cyclosporine A (CSA), but not tacrolimus (TAC), inhibits hepatitis C virus (HCV) replication in vitro. Clinical reports on the efficacy of interferon-α (IFNα)-based antiviral therapy (AVT) for recurrent HCV after liver transplantation (LT) with CSA and TAC are conflicting. Our
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