Cyclosporin A (Cyclosporine A)

Alias: Cyclosporine A;cyclosporin;Ciclosporin; cyclosporin A
Cat No.:V1858 Purity: ≥98%
Cyclosporin A (Cyclosporine A; CsA)is anaturally occuring cyclic polypeptide immunosuppressive agent and a calcineurin inhibitor, which binds to the cyclophilin and then inhibits calcineurin with IC50 of 7 nM in a cell-free assay.
Cyclosporin A (Cyclosporine A) Chemical Structure CAS No.: 59865-13-3
Product category: Molecular Glues
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Cyclosporin A (Cyclosporine A):

  • Cyclosporin A-d3 (Cyclosporin A-d3; Ciclosporin A-d3; CsA-d3)
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Cyclosporin A (Cyclosporine A; CsA) is a naturally occuring cyclic polypeptide immunosuppressive agent and a calcineurin inhibitor, which binds to the cyclophilin and then inhibits calcineurin with IC50 of 7 nM in a cell-free assay. It is widely used in organ transplantation to prevent rejection. Cyclosporin A can also be used for rheumatoid arthritis, psoriasis, Crohn's disease, nephrotic syndrome, and in organ transplants to prevent rejection. Cyclosporin A is responsible for the opening of the MPTP (mitochondrial permeability transition pore). When tested with retinal ganglion cells, Cyclosporin A showed a high selectivity for the expression of cyclophilin D and prolonged the cells survival. In human First-Trimester Trophoblast Cells, Cyclosporin A treatment promoted cells growth and invasiveness by inhibiting Ca2+/Calcineurin/NFAT signal. Cyclosporin A treatment promoted the apoptosis of T-cell by upregulating Fas/FasL and caspase activities

Biological Activity I Assay Protocols (From Reference)
ln Vitro
In T cells, cyclophilin and cyclosporin A can bind [1]. By creating the Cyclophilin-Cyclosporin A complex, cyclosporin A inhibits calcineurin [2]. With an IC50 value of 7 nM, cyclosporin A inhibits calcineurin in activated cells [3]. Cyclosporin A prevents NF-AT from moving to the nucleus [4]. With an IC50 of 39 nM, cyclosporin A inhibits mitochondrial MTP opening [5].
ln Vivo
When administered parenterally or orally to mice, rats, and guinea pigs, cyclosporine A exerts immunosuppressive effects [6]. In organ transplantation, cyclosporine A can be given to stop organ rejection [7].
Animal Protocol
Dissolved in 0.5% solution of tragacanth; 45 mg/kg; oral gavage
Rat
References
[1]. Handschumacher RE, et al. Cyclophilin: a specific cytosolic binding protein for cyclosporin A. Science. 1984 Nov 2;226(4674):544-7.
[2]. Liu J, et al. Calcineurin is a common target of cyclophilin-cyclosporin A and FKBP-FK506 complexes. Cell. 1991 Aug 23;66(4):807-15.
[3]. Fruman DA, et al. Calcineurin phosphatase activity in T lymphocytes is inhibited by FK 506 and cyclosporin A. Proc Natl Acad Sci U S A. 1992 May 1;89(9):3686-90.
[4]. Flanagan WM, et al. Nuclear association of a T-cell transcription factor blocked by FK-506 and cyclosporin A. Nature. 1991 Aug 29;352(6338):803-7.
[5]. Nicolli A, et al. Interactions of cyclophilin with the mitochondrial inner membrane and regulation of the permeability transition pore, and cyclosporin A-sensitive channel. J Biol Chem. 1996 Jan 26;271(4):2185-92.
[6]. Borel JF, et al. Effects of the new anti-lymphocytic peptide cyclosporin A in animals. Immunology. 1977 Jun;32(6):1017-25.
[7]. Williams, R, et al. Randomised trial comparing FK506 and cyclosporin in prevention of liver allograft rejection. European FK506 Multicentre Liver Study Group. Lancet, 1994, 344(8920), 423-428.
[8]. Dalmarco EM, et al. Cyclosporin A inhibits CD11a/CD18 adhesion molecules due to inhibition of TNFalpha and IL-1 beta levels in the mouse model of pleurisy induced by carrageenan. Cell Adh Migr. 2008 Oct-Dec;2(4):231-5
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C62H111N11O12
Molecular Weight
1202.61
CAS #
59865-13-3
SMILES
O([H])[C@]([H])([C@]([H])(C([H])([H])[H])C([H])([H])/C(/[H])=C(\[H])/C([H])([H])[H])[C@@]1([H])C(N([H])[C@]([H])(C(N(C([H])([H])[H])C([H])([H])C(N(C([H])([H])[H])[C@]([H])(C(N([H])[C@]([H])(C(N(C([H])([H])[H])[C@]([H])(C(N([H])[C@@]([H])(C([H])([H])[H])C(N([H])[C@]([H])(C([H])([H])[H])C(N(C([H])([H])[H])[C@@]([H])(C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])C(N(C([H])([H])[H])[C@]([H])(C(N(C([H])([H])[H])[C@]([H])(C(N1C([H])([H])[H])=O)C([H])(C([H])([H])[H])C([H])([H])[H])=O)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])=O)=O)=O)=O)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])=O)C([H])(C([H])([H])[H])C([H])([H])[H])=O)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])=O)=O)C([H])([H])C([H])([H])[H])=O
Synonyms
Cyclosporine A;cyclosporin;Ciclosporin; cyclosporin A
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO:100 mg/mL (83.2 mM)
Water:<1 mg/mL
Ethanol:100 mg/mL (83.2 mM)
Solubility (In Vivo)
2%DMSO+30%PEG 300+5%Tween 80+ddH2O: 5mg/mL
 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 0.8315 mL 4.1576 mL 8.3152 mL
5 mM 0.1663 mL 0.8315 mL 1.6630 mL
10 mM 0.0832 mL 0.4158 mL 0.8315 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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