FK-506
Product Code: AG-CN2-0047
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0047-M001 | 1 mg | £25.00 |
Quantity:
| AG-CN2-0047-M005 | 5 mg | £30.00 |
Quantity:
| AG-CN2-0047-M025 | 25 mg | £105.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
+4deg;C
Documents
Further Information
Alternate Names/Synonyms:
Tacrolimus; Fujimycin
Appearance:
White to off-white solid.
CAS:
109581-93-3
Class:
6.1
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS06
Handling Advice:
Protect from light.
Hazards:
H301
InChi:
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
InChiKey:
NWJQLQGQZSIBAF-CBLXODBSSA-N
Long Description:
Chemical. CAS: 109581-93-3. Formula: C44H69NO12 . H2O. MW: 804.0 . 18.0. Isolated from Streptomyces FCZ0311. Potent immunosuppressant (as cyclosporin A and rapamycin). Suppresses proliferation of cytotoxic T cells and inhibits the production of T cell-derived mediators such as interleukin-2 (IL-2). Forms a complex with FK-506 binding protein 12 (FKBP12). Inhibits the activity of the calcium/calmodulin-dependent protein phosphatase 2B (PP2B; calcineurin), leading to disruption of T cell activation. Prevents rejection of transplanted organs. Anti-inflammatory compound in the treatment of several inflammatory skin diseases (e.g. atopic dermatitis) and with potential anti-rheumatic activity (rheumatoid arthritis). Neuroprotective. Regulates nitric oxide neurotoxicity. Neurotransmitter. Ca2+ release compound. NF-kappaB suppressor by induction of unfolded protein response (UPR). Anti-cancer compound. Apoptosis inducer.
MDL:
MFCD11045918
Molecular Formula:
C44H69NO12 . H2O
Molecular Weight:
804.0 . 18.0
Package Type:
Vial
PG:
III
Precautions:
P301, P310, P330
Product Description:
Potent immunosuppressant (as cyclosporin A and rapamycin) [1-3]. Suppresses proliferation of cytotoxic T cells and inhibits the production of T cell-derived mediators such as interleukin-2 (IL-2) [2, 4]. Forms a complex with FK-506 binding protein 12 (FKBP12). Inhibits the activity of the calcium/calmodulin-dependent protein phosphatase 2B (PP2B; calcineurin), leading to disruption of T cell activation [2, 4, 6, 7]. Prevents rejection of transplanted organs [3]. Anti-inflammatory compound in the treatment of several inflammatory skin diseases (e.g. atopic dermatitis) and with potential anti-rheumatic activity (rheumatoid arthritis) [5, 9]. Neuroprotective. Regulates nitric oxide neurotoxicity. Neurotransmitter. Ca2+ release compound [8]. NF-kappaB suppressor by induction of unfolded protein response (UPR) [11]. Anti-cancer compound. Apoptosis inducer [10, 12].
Purity:
>98% (HPLC)
Signal word:
Danger
SMILES:
[H]O[H].[H][C@]1(CC[C@@]([H])(O)[C@@]([H])(C1)OC)C=C(/C)[C@@]1([H])OC(=O)C2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@]([H])([C@H](C[C@@]2([H])C)OC)[C@]([H])(C[C@@]([H])(C)CC(C)=C[C@@]([H])(CC=C)C(=O)CC(O)[C@@]1([H])C)OC
Solubility Chemicals:
Soluble in DMSO, ethanol, methanol, ethyl acetate or acetone. Insoluble in water.
Source / Host:
Isolated from Streptomyces tsukubaensis.
Transportation:
Excepted Quantity
UN Nummer:
UN 2811
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
FK-506, a novel immunosuppressant isolated from a Streptomyces. I. Fermentation, isolation, and physico-chemical and biological characteristics: T. Kino, et al.; J. Antibiot. (Tokyo) 40, 1249 (1987) | Cyclosporin A, FK506 and rapamycin: more than just immunosuppression: J. Kunz & M.N. Hall; TIBS 18, 334 (1993) | Cyclosporin A and FK506: molecular mechanisms of immunosuppression and probes for transplantation biology: B.E. Bierer, et al.; Curr. Opin. Immunol. 5, 763 (1993) | The actions of cyclosporin A and FK506 on T-lymphocyte activation: P.S. Mattila; Biochem. Soc. Trans. 24, 45 (1996) (Review) | FK506 in the treatment of inflammatory skin disease: promises and perspectives: G. Michel, et al.; Immunol. Today 17, 106 (1996) (Review) | The mechanism of action of cyclosporin A and FK506: S. Ho, et al.; Clin. Immunol. Immunopathol. 80, S40 (1996) (Review) | FK506, an immunosuppressant targeting calcineurin function: F.J. Dumont; Curr. Med. Chem. 7, 731 (2000) (Review) | FK506 and its analogs - therapeutic potential for neurological disorders: A. Klettner & T. Herdegen; Curr. Drug Targets CNS Neurol. Disord. 2, 153 (2003) (Review) | A review of the action of tacrolimus (FK506) on experimental models of rheumatoid arthritis: S. Miyata, et al.; Inflamm. Res. 54, 1 (2005) (Review) | Metabolism of tacrolimus (FK506) and recent topics in clinical pharmacokinetics: K. Iwasaki; Drug Metab. Pharmacokinet. 22, 328 (2007) (Review) | Suppression of NF-kappaB by cyclosporin A and tacrolimus (FK506) via induction of the C/EBP family: implication for unfolded protein response: S. Du, et al.; J. Immunol. 182, 7201 (2009) | FK506 binding proteins as targets in anticancer therapy: S. Romano, et al.; Anticancer Agents Med. Chem. 10, 651 (2010) (Review)