Cyclosporin A

Cyclosporin A (Cyclosporine A) is an immunosuppressant which binds to the cyclophilin and inhibits phosphatase activity of protein phosphatase 2B (PP2B/calcineurin) with an IC50 of 5 nM[3]. Cyclosporin A also inhibits CD11a/CD18 adhesion[8].

Product Specifications

CAS Number

[59865-13-3]

Product Name Alternative

Cyclosporine A; Ciclosporin A; CsA

UNSPSC

12352005

Hazard Statement

H302, H350, H360

Target

Antibiotic; Complement System; Cyclophilin; Molecular Glues

Type

Natural Products

Related Pathways

Anti-infection; Immunology/Inflammation; PROTAC

Applications

COVID-19-immunoregulation

Field of Research

Inflammation/Immunology; Cancer

Assay Protocol

https://www.medchemexpress.com/cyclosporin-a.html

Purity

99.94

Solubility

DMSO : 62.5 mg/mL (ultrasonic) |Ethanol : 50 mg/mL (ultrasonic)

Smiles

C/C=C/C[C@H]([C@@H](O)[C@@]1(N(C)C([C@]([H])(C(C)C)N(C)C([C@H](CC(C)C)N(C)C([C@]([H])(CC(C)C)N(C)C([C@@H](C)NC([C@H](C)NC([C@@H](N(C([C@@]([H])(NC([C@@H](N(C(CN(C([C@@H](NC1=O)CC)=O)C)=O)C)CC(C)C)=O)C(C)C)=O)C)CC(C)C)=O)=O)=O)=O)=O)=O)[H])C

Molecular Formula

C62H111N11O12

Molecular Weight

1202.61

Precautions

H302, H350, H360

References & Citations

[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.|[9]Medeiros M, et al. Increased cyclosporine bioavailability induced by experimental nephrotic syndrome in rats. Can J Physiol Pharmacol. 2007 May;85 (5) :502-6.|[10]Nguyen LT, et al. Lysyl oxidase inhibitors attenuate cyclosporin A-induced nephropathy in mouse. Sci Rep. 2021 Jun 14;11 (1) :12437.|[11]Ling H, et al. Therapeutic role of TGF-beta-neutralizing antibody in mouse cyclosporin A nephropathy: morphologic improvement associated with functional preservation. J Am Soc Nephrol. 2003 Feb;14 (2) :377-88.