32425

Cyclosporin A

VETRANAL^®, analytical standard

• Synonym(s): Antibiotic S 7481F1, Cyclosporine
• Empirical Formula (Hill Notation): C₆₂H₁₁₁N₁₁O₁₂
• CAS Number: 59865-13-3
• Molecular Weight: 1202.61
• Beilstein/REAXYS Number: 3647785
• MDL number: MFCD00274558
• UNSPSC Code: 41116107
• PubChem Substance ID: 329754203
• NACRES: NA.24

Properties

• grade: analytical standard
• Quality Level: 100
• product line: VETRANAL^®
• shelf life: limited shelf life, expiry date on the label
• technique(s): HPLC: suitable; gas chromatography (GC): suitable
• application(s): 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

Description

General description

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.[1][2][3]

Cyclosporin A has been used to:

• Prevent rejection of kidney and liver transplants.[1]
• In graft versus host disease.[1]
• Treatment of autoimmune diseases.[1]
• Treatment of Schistosomiasis.[1]

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.

Potent immunosuppressant; inhibits nitric oxide synthesis induced by interleukin 1α, lipopolysaccharides and TNFα; blocks cytochrome c release from mitochondria.

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• pictograms: GHS08,GHS07
• signalword: Danger
• hcodes: H302,H350,H360FD
• pcodes: P201 - P202 - P264 - P270 - P301 + P312 - P308 + P313
• Hazard Classifications: Acute Tox. 4 Oral - Carc. 1B - Repr. 1B
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3