All Photos(1)

Documents

F4679

FK-506 monohydrate

Name: FK-506 monohydrate
Brand: SIGMA

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

Synonym(s):

Tacrolimus

Sign Into View Organizational & Contract Pricing

All Photos(1)

About This Item

Empirical Formula (Hill Notation):

C₄₄H₆₉NO₁₂ · H₂O

CAS Number:

109581-93-3

Molecular Weight:

822.03

MDL number:

MFCD11045918

UNSPSC Code:

12352200

PubChem Substance ID:

24724482

NACRES:

NA.77

product name

FK-506 monohydrate, ≥98% (HPLC)

Quality Level

100

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)

Looking for similar products? Visit Product Comparison Guide

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).

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

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)

View All Related Papers

Articles

Discover Bioactive Small Molecules for ADME/Tox

DISCOVER Bioactive Small Molecules for Neuroscience

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service