AdipoGen Life Sciences

Cyclosporin A

CHF 55.00
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AG-CN2-0079-M100100 mgCHF 55.00
AG-CN2-0079-51005 x 100 mgCHF 165.00
AG-CN2-0079-G0011 gCHF 190.00
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Product Details
Synonyms Antibiotic S 7481F1; Ciclosporin A; CsA; Cyclosporine; NSC 290193; Ramihyphin A
Product Type Chemical
Properties
Formula

C62H111N11O12

MW 1202.6
Merck Index 14: 2752
CAS 59865-13-3
RTECS GZ4120000
Source/Host Chemicals Isolated from Tolypocladium inflatum.
Purity Chemicals ≥98%
Appearance White solid.
Solubility Soluble in DMSO, ethanol, methanol, dichlormethane, chloroform or acetone. Insoluble in water.
InChi Key PMATZTZNYRCHOR-VPYFBNRVBI
Smiles [H][C@@]1([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)C(C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C(=O)[C@H](CC)NC1=O)C(C)C
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Use/Stability Stable for at least 3 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
Description
  • Potent immunosuppressant (same as FK-506 (Prod. No. AG-CN2-0047) and rapamycin (Prod. No. AG-CN2-0025)).
  • Forms a complex with cyclophilin. Inhibits the activity of the calcium/calmodulin-dependent protein phosphatase 2B (PP2B; calcineurin). Prevents the dephosphorylation of nuclear factor of activated T cells (NFAT) transcription factor, leading to disruption of T cell activation.
  • Suppresses proliferation of cytotoxic T cells and inhibits the production of T cell-derived mediators such as interleukin-2 (IL-2).
  • 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).
  • Antibacterial. Antifungal. Antiparasitic.
  • Apoptosis inhibitor. Inhibits the mitochondrial permeability transition pore (MPTP) from opening, thus inhibiting cytochrome c release.
  • NF-κB suppressor by induction of unfolded protein response (UPR).
  • Anti-cancer compound. Apoptosis and autophagy inducer.
  • Inhibits nitric oxide synthesis induced by interleukin-1α, lipopolysaccharides and TNF-α.
  • Potently induces highly cardiogenic progenitors from embryonic stem (ES) cells.
Product References
  1. Calcineurin phosphatase activity in T lymphocytes is inhibited by FK 506 and cyclosporin A: D.A. Fruman, et al.; PNAS 89, 3686 (1992)
  2. Cyclosporin A, FK506 and rapamycin: more than just immunosuppression: J. Kunz & M.N. Hall; TIBS 18, 334 (1993)
  3. Cyclosporin A and FK506: molecular mechanisms of immunosuppression and probes for transplantation biology: B.E. Bierer, et al.; Curr. Opin. Immunol. 5, 763 (1993)
  4. Immunological actions of cyclosporin A in rheumatoid arthritis: D. Yocum; Br. J. Rheumatol. 32, 38 (1993)
  5. The antimicrobial activities of cyclosporine, FK506, and rapamycin: H.P. High; Tansplantation 57, 1689 (1994) (Review)
  6. Identification of immunosuppressant-induced apoptosis in a murine B-cell line and its prevention by bcl-x but not bcl-2: A.R. Gottschalk, et al.; PNAS 91, 7350 (1994)
  7. Inhibition of the mitochondrial permeability transition pore by cyclosporin A during long time frame experiments: relationship between pore opening and the activity of mitochondrial phospholipases. K.M. Broekemeier & D.R. Pfeiffer; Biochemistry 34, 16440 (1995)
  8. Effects of cyclosporin A and FK506 on nitric oxide and tetrahydrobiopterin synthesis in bacterial lipopolysaccharide-treated J774 macrophages: Y. Hattori & N. Naranishi; Cell Immunol. 165, 7 (1995)
  9. Inhibition of T lymphocyte activation and apoptotic cell death by cyclosporin A and tacrolimus (FK506). Its relevance to therapy of HIV infection: A.W. Thomson & C.A. Bonham; Adv. Exp. Med. Biol. 374, 211 (1995) (Review)
  10. FK506 in the treatment of inflammatory skin disease: promises and perspectives: G. Michel, et al.; Immunol. Today 17, 106 (1996) (Review)
  11. The antiparasite effects of cyclosporin A: possible drug targets and clinical applications: A. Bell, et al.; Gen. Pharmacol. 27, 963 (1996) (Review)
  12. The mechanism of action of cyclosporin A and FK506: S. Ho, et al.; Clin. Immunol. Immunopathol. 80, S40 (1996) (Review)
  13. Calcineurin phosphatase activity and immunosuppression. A review on the role of calcineurin phosphatase activity and the immunosuppressive effect of cyclosporin A and tacrolimus: K.A. Jorgensen, et al.; Scand. J. Immunol. 57, 93 (2003) (Review)
  14. 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)
  15. Melatonin suppresses cyclosporine A-induced autophagy in rat pituitary GH3 cells: Y.M. Yoo & E.B. Jeung; J. Pineal Res. 48, 204 (2010)
  16. Cyclosporin-A potently induces highly cardiogenic progenitors from embryonic stem cells: P. Yan, et al.; BBRC 379, 115 (2009)
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