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Key Documents

F4679

Sigma-Aldrich

FK-506 monohydrate

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

Synonyme(s) :

Tacrolimus

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About This Item

Formule empirique (notation de Hill):
C44H69NO12 · H2O
Numéro CAS:
Poids moléculaire :
822.03
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

product name

FK-506 monohydrate, ≥98% (HPLC)

Pureté

≥98% (HPLC)

Forme

powder

Solubilité

DMSO: 20 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

NWJQLQGQZSIBAF-MLAUYUEBSA-N

Informations sur le gène

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

Actions biochimiques/physiologiques

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).

Caractéristiques et avantages

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.

Pictogrammes

Skull and crossbones

Mention d'avertissement

Danger

Mentions de danger

Conseils de prudence

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

Neuroregenerative and neuroprotective actions of neuroimmunophilin compounds in traumatic and inflammatory neuropathies
Gold Bruce G, et al.
Neurological Research, 26(4), 371-380 (2004)
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
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)

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