| Source: | Streptomyces tsukubaensis |
| Synonyms | FK506, Tacrolimus, Tsukubaenolide
Fujimycin, FK5, Prograf , Protopic, Tacarolimus |
| Description: | Tacrolimus is 23-membered macrolide lactone discovered in 1984, by Kino T, Hatanaka H and Hashimoto M. [reference 2] Tacrolimus 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. Tacrolimus 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: | 
 |
| Molecular Formula: | C44H69NO12 |
Solubility
information: | - Tacrolimus is soluble in Methanol, Ethanol, Acetone, Ethyl Acetate, Diethyl ether, Chloroform, Dicloromethane.
- Tacrolimus is sparingly soluble in Hexane, Petroleum ether.
- Tacrolimus 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 point | 127oC - 130oC |
| Solubility | Clear colorless solution at 10 mg/ml of: Dichloromethane, Ethyl Acetate, DMSO |
| Storage | Store as supplied at 4oC. Protect from moisture. The FK506 powder is stable for 3 years as supplied. |
| Applications | FK506 (Tacrolimus) is used as an immunosuppressantat organ transplantations.
FK506 is used , as ointment, as a treatment for dermatitis. |
| Warnings | |
| Classification | macrolide
immunosupressor |
| Related products | Ascomycin (FK520) |
| | For Research use only. Not for Human or Drug use
GMP/API grade available on request
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.
tacrolimus, 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 Tacrolimus 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.
Tacrolimus 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 Tacrolimus.
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.
Oral Dis. 2006 May;12(3):309-14. |
| | 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 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 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 and triamcinolone acetonide ointment.
Acta Derm Venereol. 2006;86(3):227-9. |
| | Sugiyama K, Arakawa K, Satoh H, Saito K, Takahashi K, Saito N, Hirano T.
Correlation between pharmacological efficacy of cyclosporine A and Tacrolimus , evaluated by lymphocyte immunosuppressant-sensitivity test (LIST) with MTT assay procedure in renal transplant recipients.
J Immunoassay Immunochem. 2006;27(2):195-205. |
| | Blanchard SS, Gerrek M, Czinn S, Chelimsky G, Seaman D, Siegel C, Splawski J.
Food protein sensitivity with partial villous atrophy after pediatric liver transplantation with Tacrolimus (FK506) immunosuppression.
Pediatr Transplant. 2006 Jun;10(4):529-32. |
| | Lupp A, Kuhn UD, Karge E, Adam G, Fleck C.
Ro investigations on the differential pro-oxidant and/or antioxidant properties of cyclosporin A and Tacrolimus in human and rat liver microsomes.
Int J Clin Pharmacol Ther. 2006 May;44(5):225-32. |
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