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C3662

Sigma-Aldrich

Cyclosporin A

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

Synonym(s):
Antibiotic S 7481F1, Cyclosporine
Empirical Formula (Hill Notation):
C62H111N11O12
CAS Number:
Molecular Weight:
1202.61
Beilstein:
3647785
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

Tolypocladium inflatum

Quality Level

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

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This Item
30024C183232425
Cyclosporin A from Tolypocladium inflatum, ≥95% (HPLC), solid

Sigma-Aldrich

C3662

Cyclosporin A

Cyclosporin A 97.0-101.5% (on dried basis)

Sigma-Aldrich

30024

Cyclosporin A

Cyclosporin A from Tolypocladium inflatum, BioReagent, for molecular biology, ≥95%

Sigma-Aldrich

C1832

Cyclosporin A

Cyclosporin A VETRANAL®, analytical standard

Supelco

32425

Cyclosporin A

assay

≥95% (HPLC)

assay

97.0-101.5% (on dried basis)

assay

≥95%

assay

-

form

solid

form

powder

form

powder

form

-

color

white

color

white to off-white

color

-

color

-

solubility

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

solubility

-

solubility

dichloromethane: 9.80-10.20 mg/mL, clear, colorless to faintly yellow

solubility

-

originator

Novartis

originator

-

originator

-

originator

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

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.

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.

Pictograms

Exclamation markHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

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

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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