Cyclosporin A
Product Code: AG-CN2-0079
Product Group: Natural Products and Extracts
Supplier: AdipoGen Life Sciences
| Code | Size | Price |
|---|
| AG-CN2-0079-M100 | 100 mg | £50.00 |
Quantity:
| AG-CN2-0079-5100 | 5 x 100 mg | £130.00 |
Quantity:
| AG-CN2-0079-G001 | 1 g | £160.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
Ambient
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
Antibiotic S 7481F1; Ciclosporin A; CsA; Cyclosporine; NSC 290193; Ramihyphin A
Appearance:
White solid.
CAS:
59865-13-3
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07,GHS08
Handling Advice:
Keep cool and dry.
Hazards:
H302, H350, H360
InChi:
InChI=1/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(39(13)14)62(85)73(51)24/h25,27,34-47,49-52,75H,26,28-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b27-25+/t40-,41+,42-,43+,44+,45+,46+,47+,49+,50?,51+,52-/m1/s1
InChiKey:
PMATZTZNYRCHOR-VPYFBNRVBI
Long Description:
Chemical. CAS: 59865-13-3. Formula: C62H111N11O12. MW: 1202.6. Isolated from Tolypocladium inflatum. 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-kappaB suppressor by induction of unfolded protein response (UPR). Anti-cancer compound. Apoptosis and autophagy inducer. Inhibits nitric oxide synthesis induced by interleukin-1alpha, lipopolysaccharides and TNF-alpha. Potently induces highly cardiogenic progenitors from embryonic stem (ES) cells.
MDL:
MFCD00274558
Molecular Formula:
C62H111N11O12
Molecular Weight:
1202.6
Package Type:
Vial
Precautions:
P301, P312, P308, P313, P330
Product 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-kappaB suppressor by induction of unfolded protein response (UPR). Anti-cancer compound. Apoptosis and autophagy inducer. Inhibits nitric oxide synthesis induced by interleukin-1alpha, lipopolysaccharides and TNF-alpha. Potently induces highly cardiogenic progenitors from embryonic stem (ES) cells.
Purity:
>98%
Signal word:
Danger
SMILES:
[H][C@@]1([C@H](O)[C@H](C)CC=CC)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
Solubility Chemicals:
Soluble in DMSO, ethanol, methanol, dichlormethane, chloroform or acetone. Insoluble in water.
Source / Host:
Isolated from Tolypocladium inflatum.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 3 years after receipt when stored at -20°C.
References
Calcineurin phosphatase activity in T lymphocytes is inhibited by FK 506 and cyclosporin A: D.A. Fruman, et al.; PNAS 89, 3686 (1992) | 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) | Immunological actions of cyclosporin A in rheumatoid arthritis: D. Yocum; Br. J. Rheumatol. 32, 38 (1993) | The antimicrobial activities of cyclosporine, FK506, and rapamycin: H.P. High; Tansplantation 57, 1689 (1994) (Review) | 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) | 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) | 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) | 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) | FK506 in the treatment of inflammatory skin disease: promises and perspectives: G. Michel, et al.; Immunol. Today 17, 106 (1996) (Review) | The antiparasite effects of cyclosporin A: possible drug targets and clinical applications: A. Bell, et al.; Gen. Pharmacol. 27, 963 (1996) (Review) | The mechanism of action of cyclosporin A and FK506: S. Ho, et al.; Clin. Immunol. Immunopathol. 80, S40 (1996) (Review) | 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) | 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) | Melatonin suppresses cyclosporine A-induced autophagy in rat pituitary GH3 cells: Y.M. Yoo & E.B. Jeung; J. Pineal Res. 48, 204 (2010) | Cyclosporin-A potently induces highly cardiogenic progenitors from embryonic stem cells: P. Yan, et al.; BBRC 379, 115 (2009)
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