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Merck

30024

Cyclosporin A

97.0-101.5% (on dried basis)

Sinónimos:

Antibiotic S 7481F1, Cyclosporine

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Fórmula empírica (notación de Hill):
C62H111N11O12
Número CAS:
59865-13-3
Peso molecular:
1202.61
UNSPSC Code:
51102829
NACRES:
NA.76
PubChem Substance ID:
57648402
MDL number:
MFCD00274558
Beilstein/REAXYS Number:
3647785

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Nombre del producto

Cyclosporin A, 97.0-101.5% (on dried basis)

InChI key

PMATZTZNYRCHOR-CGLBZJNRSA-N

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

assay

97.0-101.5% (on dried basis)

form

powder

color

white to off-white

antibiotic activity spectrum

fungi

mode of action

enzyme | inhibits

storage temp.

2-8°C

Quality Level

200

Gene Information

human ... PPIA(5478)

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Categorías relacionadas

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

General description

Chemical structure: peptide

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Repr. 1B

Clase de almacenamiento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificados de análisis (COA)

Lot/Batch Number
088M4082V
098M4084V
098M4083V
088M4081V
127M4017V

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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
Franziska Böttger et al.
Cell reports, 27(11), 3345-3358 (2019-06-13)
Small-cell lung cancer is the most aggressive type of lung cancer, characterized by a remarkable response to chemotherapy followed by development of resistance. Here, we describe SCLC subtypes in Mycl- and Nfib-driven GEMM that include CDH1-high peripheral primary tumor lesions
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
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
Mi-Yeon Jang et al.
Journal of medicinal chemistry, 54(2), 655-668 (2010-12-22)
Herein we describe the synthesis and in vitro and in vivo activity of thiazolo[5,4-d]pyrimidines as a novel class of immunosuppressive agents, useful for preventing graft rejection after organ transplantation. This research resulted in the discovery of a series of compounds
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