30024

Sigma-Aldrich

Cyclosporin A

98.5-101.5% (on dried basis)

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:
Pricing and availability is not currently available.

Quality Level

assay

98.5-101.5% (on dried basis)

form

powder or crystals

color

white to off-white

Mode of action

enzyme | inhibits

antibiotic activity spectrum

fungi

storage temp.

2-8°C

SMILES string

CCC@@H1NC(=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)

Looking for similar products? Visit Product Comparison Guide

Related Categories

General description

Chemical structure: peptide

Packaging

25, 100 mg in glass bottle
Bottomless glass bottle. Contents are inside inserted fused cone.

Application

Cyclosporin A is used for immunosuppressive studies .

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.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.Storage class (TRGS 510): Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects.

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

T

Risk Statement

45-60-22

Safety Statement

53-45

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Certificate of Analysis
Certificate of Origin
Valerie Waters et al.
American journal of respiratory cell and molecular biology, 33(2), 138-144 (2005-05-10)
Cyclosporin A (CsA) blocks T cell activation by interfering with the Ca2+-dependent phosphatase, calcineurin. Proinflammatory responses to bacteria that are activated by Ca2+-fluxes in airway cells are a potential target for CsA. Although local immunosuppression may be advantageous to control...
C Frieke Kuper et al.
Toxicologic pathology, 35(2), 226-232 (2007-03-17)
The effects of cyclosporin A (CY) and cyclophosphamide (CPS) on Peyer's patches (PP) were studied in Wistar rats, exposed in utero and neonatally or during adult age. In one study, pregnant dams received 5 or 15 mg/kg bw/day CY from...
Sébastien Combes et al.
Journal of medicinal chemistry, 54(9), 3153-3162 (2011-04-15)
A series of A-ring variously methoxylated 4-(3-hydroxy-4-methoxyphenyl)coumarins related to combretastatin A-4 was prepared by cross-coupling reactions. Cytotoxicity studies indicated a potent activity against HBL100 cell line. Substitution patterns on A-ring had only a slight effect on antiproliferative activity. For most...
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...
Roger G Ptak et al.
Antimicrobial agents and chemotherapy, 52(4), 1302-1317 (2008-01-24)
Debio-025 is a synthetic cyclosporine with no immunosuppressive capacity but a high inhibitory potency against cyclophilin A (CypA)-associated cis-trans prolyl isomerase (PPIase) activity. A lack of immunosuppressive effects compared to that of cyclosporine was demonstrated both in vitro and in...
Articles
Nitric oxide (NO) as a signal transporter in neurons, endothelial cells and in the immune system.
Read More

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.