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cancer research reagents

FK506

MSDSSample CoA
 
Source: Streptomyces tsukubaensis
SynonymsFK506, Tacrolimus, Tsukubaenolide
Fujimycin, FK5, Prograf , Protopic, Tacarolimus
  
Description: FK506 is 23-membered macrolide lactone discovered in 1984, by Kino T, Hatanaka H and Hashimoto M. [reference 2]

FK506  exhibits potent inhibitory effect on T- lymphocyte activation. It binds to immunophilins FK506 binding proteins (FKBP-12) and a complex of FKBP-12, calcium, calmodulin and calcineurin is formed, inhibiting phosphatase activity of calcineurin. This prevents dephosphorylation and translocation of nuclear factor of activated T – cells (NF-AT) and inhibits transcription of early T-cell activation gene, Interleukin-2, Tumour Necrosis Factor (TNF-a) and proto-oncogenes; suppressing expression of IL-2 and IL-7 receptor. This results in inhibition of T-lymphocyte activation. FK506  also inhibits the mixed lymphocyte reaction, generation of cytotoxic T-cells and T-cell dependent B-cell activation.[reference 1] 

CAS number: 104987-11-3
Merck index: 13:9117
Molecular weight: 804
Structure:

tacrolimus - fk506 structure

 

Molecular Formula: C44H69NO12
Canonical SMILES:  
Solubility
information:
  • FK506  is soluble in Methanol, Ethanol, Acetone, Ethyl Acetate, Diethyl ether, Chloroform, Dicloromethane.
  • FK506  is sparingly soluble in Hexane, Petroleum ether.
  • FK506  is insoluble in water
Specifications 
Appearance: White crystalline powder
Purity: TLC (normal, Ethyl Acetate) : >98%                               Current lot: >99%
TLC (reverse C18, Methanol : water 9:1): >98%         Current lot: >99%
λmax: 
Melting point127oC - 130oC
SolubilityClear colorless solution at 10 mg/ml of: Dichloromethane, Ethyl Acetate, DMSO
StorageStore at -18oC. Protect from moisture.
ApplicationsFK506 (Tacrolimus) is used as an immunosuppressant at organ transplantations.
FK506 is used , as oinment, as a treatment for dermatitis.
For experimental uses of FK506 (Tacrolimus) read also United States Patent Application 20090098200
Warnings
Classificationmacrolide
immunosuppressant
Related products
  Ascomycin (FK520)  

 

 For Research use only. Not for Human or Drug use
GMP/API grade available on request
 

Animal Free productNo raw materials from
animal source were used


No genetically modified organisms are used.

Publications 
 1. Spencer CM, Goa KL and Gillis JC.
Tacrolimus. An update of its pharmacology and clinical efficacy in the management of organ transplantation.
Drugs 1997;54(6):925-75.
 2. Kino T, Hatanaka H, Hashimoto M et al.
FK-506, a novel immunosuppressant isolated from a Streptomyces. I. Fermentation, isolation, and physicochemical and biological characteristics.
J Antibiot (Tokyo) 1987; 40: 1249–1255.
 Lubitz SA, Baran DA, Alwarshetty MM, Pinney S, Kaplan S, Chan M, Courtney MC, Lansman SL, Spielvogel D, Gass AL.
Long-term Results of FK506 Monotherapy in Cardiac Transplant Recipients.
J Heart Lung Transplant. 2006 Jun;25(6):699-706
 Nivenius E, van der Ploeg I, Jung K, Chryssanthou E, van Hage M, Montan PG.
FK506 ointment vs steroid ointment for eyelid dermatitis in patients with atopic keratoconjunctivitis.
Eye. 2006 May 5
 Tsuboi H, Yonemoto K, Katsuoka K.
A 14-year-old girl with lichenoid sarcoidosis successfully treated with FK506.
J Dermatol. 2006 May;33(5):344-8
 Spolidorio LC, Spolidorio DM, Massucato EM, Neppelenbroek KH, Campanha NH, Sanches MH.
Oral health in renal transplant recipients administered cyclosporin A or Tacrolimus (FK506).
Oral Dis. 2006 May;12(3):309-14.
 Dotsch J, Dittrich K, Plank C, Rascher W.
Is Tacrolimus (FK506) for childhood steroid-dependent nephrotic syndrome better than ciclosporin A?
Nephrol Dial Transplant. 2006 May 15
 Fukatsu S, Fukudo M, Masuda S, Yano I, Katsura T, Ogura Y, Oike F, Takada Y, Inui K.
Delayed effect of grapefruit juice on pharmacokinetics and pharmacodynamics of Tacrolimus (FK506) in a living-donor liver transplant recipient.
Drug Metab Pharmacokinet. 2006 Apr;21(2):122-5.
 Aihaiti X, Hayamizu K, Oishi K, Yoshimitsu M, Itamoto T, Asahara T.
Facilitation of survival in a rat fulminant hepatic failure model by combination therapy using recombinant G-CSF and Tacrolimus (FK506).
J Interferon Cytokine Res. 2006 Apr;26(4):226-34.
 Shah S, Budev M, Blazey H, Fairbanks K, Mehta A.
Hepatic veno-occlusive disease due to Tacrolimus (FK506) in a single-lung transplant patient.
Eur Respir J. 2006 May;27(5):1066-8.
 Ponseti JM, Azem J, Fort JM, Lopez-Cano M, Vilallonga R, Gamez J, Armengol M.
Experience with starting Tacrolimus (FK506) postoperatively after transsternal extended thymectomy in patients with myasthenia gravis.
Curr Med Res Opin. 2006 May;22(5):885-95.
 Laeijendecker R, Tank B, Dekker SK, Neumann HA.
A comparison of treatment of oral lichen planus with topical Tacrolimus (FK506) and triamcinolone acetonide ointment.
Acta Derm Venereol. 2006;86(3):227-9.

Streptomyces tsukubaensis

 



FK506 on Wikipedia


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