32425

Supelco

Cyclosporin A

VETRANAL®, analytical standard

Synonym(s):
Antibiotic S 7481F1, Cyclosporine
Empirical Formula (Hill Notation):
C62H111N11O12
CAS Number:
Molecular Weight:
1202.61
Beilstein/REAXYS Number:
3647785
MDL number:
PubChem Substance ID:
NACRES:
NA.24

Quality Level

grade

analytical standard

product line

VETRANAL®

form

neat

shelf life

limited shelf life, expiry date on the label

application(s)

HPLC: suitable
gas chromatography (GC): suitable

Featured Industry

Forensics and Toxicology
Pharmaceutical (small molecule)

format

neat

SMILES string

CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](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)C1=O)C(C)C

InChI

1S/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

InChI key

PMATZTZNYRCHOR-CGLBZJNRSA-N

Gene Information

human ... PPIA(5478)

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General description

Cyclosporin A has been used to:
  • Prevent rejection of kidney and liver transplants.
  • In graft versus host disease.
  • Treatment of autoimmune diseases.
  • Treatment of Schistosomiasis.
Cyclosporin A (CsA) is a fungal metabolite, a cyclic undecapeptide. It has highly specific immunosuppressive effects with low myelotoxicity, thereby making it a valuable drug in human organ transplantation. Its immunosuppressive activity is based upon its ability to inhibit early steps of T-lymphocyte activation such as lymphokine gene transcription.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

A fungal metabolite possessing potent immunosuppressive properties. It inhibits the T-cell receptor signal transduction pathway via the formation of cyclosporin A−cyclophilin complex that inhibits calcineurin (protein phosphatase 2B). Inhibits nitric oxide synthesis induced by interleukin 1α, lipopolysaccharides and TNFα. Can block cytochrome c release from mitochondria.

Legal Information

VETRANAL is a registered trademark of Sigma-Aldrich Chemie GmbH

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Statements

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Certificate of Analysis

Certificate of Origin

Cyclosporin A specifically inhibits function of nuclear proteins involved in T cell activation.
Emmel, Elizabeth A., et al.
Science, 246 (4937), 1617-1617 (1989)
Cyclosporin A inhibits T-cell growth factor gene expression at the level of mRNA transcription.
Kronke, M., et al.
Proceedings of the National Academy of Sciences of the USA, 81 (16), 5214-5218 (1984)
R E Handschumacher et al.
Science (New York, N.Y.), 226(4674), 544-547 (1984-11-02)
Cyclophilin, a specific cytosolic binding protein responsible for the concentration of the immunosuppressant cyclosporin A by lymphoid cells, was purified to homogeneity from bovine thymocytes. Cation-exchange high-performance liquid chromatography resolved a major and minor cyclophilin species that bind cyclosporin A...
Lotte Coelmont et al.
Antimicrobial agents and chemotherapy, 53(3), 967-976 (2008-12-24)
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Xiao-Ling Liu et al.
Bioorganic & medicinal chemistry, 16(1), 171-180 (2007-10-30)
A library of chalcones with basic functionalities were screened for inhibition of P-glycoprotein (Pgp, ABCB1) by the calcein-AM accumulation assay on MDCKII/MDR1 cells. Three members that had ring A substituted with 5-(1-ethylpiperidin-4-yl) and 2,4-dimethoxy groups were found to increase calcein-AM...

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