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C3662

Cyclosporin A

Name: Cyclosporin A
Brand: SIGMA

from Tolypocladium inflatum, ≥95% (HPLC), solid, Calcineurin inhibitor

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

NACRES:

NA.77

PubChem Substance ID:

24278028

UNSPSC Code:

12352200

MDL number:

MFCD00274558

Beilstein/REAXYS Number:

3647785

Assay:

≥95% (HPLC)

Form:

solid

Quality level:

300

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Properties

Product Name

Cyclosporin A, from Tolypocladium inflatum, ≥95% (HPLC), solid

biological source

Tolypocladium inflatum

Quality Level

300

assay

≥95% (HPLC)

form

solid

color

white

solubility

dichloromethane: 10 mg/mL, ethanol: 10 mg/mL, DMSO: 50 mg/mL, chloroform: 6 mg/mL, H₂O: insoluble

antibiotic activity spectrum

fungi

mode of action

enzyme | inhibits

originator

Novartis

storage temp.

2-8°C

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), PPP3CA(5530), PPP3CB(5532), PPP3CC(5533), PPP3R1(5534), PPP3R2(5535)

Description

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.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Phosphoprotein Phosphatases (Serine/Threonine) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Novartis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

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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

WGK 3

ppe

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

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