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Merck

32425

Cyclosporin A

VETRANAL®, analytical standard

Synonym(s):

Antibiotic S 7481F1, Cyclosporine

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About This Item

Empirical Formula (Hill Notation):
C62H111N11O12
CAS Number:
59865-13-3
Molecular Weight:
1202.61
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329754203
MDL number:
MFCD00274558
Beilstein/REAXYS Number:
3647785

Product Name

Cyclosporin A, VETRANAL®, analytical standard

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

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 key

PMATZTZNYRCHOR-CGLBZJNRSA-N

grade

analytical standard

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

Quality Level

100

Gene Information

human ... PPIA(5478)

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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.

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.
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.

Legal Information

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

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

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

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL9391
BCCF3176
BCCC6655
BCBS4825V

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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)
Debio 025 is a potent inhibitor of hepatitis C virus (HCV) replication (J. Paeshuyse et al., Hepatology 43:761-770, 2006). In phase I clinical studies, monotherapy (a Debio 025 dose of 1,200 mg twice a day) resulted in a mean maximal
Jan Paeshuyse et al.
Antimicrobial agents and chemotherapy, 52(9), 3433-3437 (2008-07-16)
We report here a comparative study of the anti-hepatitis C virus (HCV) activities of selected (i) nucleoside polymerase, (ii) nonnucleoside polymerase, (iii) alpha,gamma-diketo acid polymerase, (iv) NS3 protease, and (v) helicase inhibitors, as well as (vi) cyclophilin binding molecules and
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