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Merck

C3662

Sigma-Aldrich

Cyclosporin A

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
Beilstein:
3647785
MDL number:
MFCD00274558
UNSPSC Code:
12352200
PubChem Substance ID:
24278028
NACRES:
NA.77

Key Documents

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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)

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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.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H302,H350,H360FD

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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Certificates of Analysis (COA)

Lot/Batch Number
098M4002V
118M4095V
057M4038V
078M4046V
14170904

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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
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
Javier Koh et al.
Nature communications, 10(1), 2820-2820 (2019-06-30)
Bats are unusual mammals, with the ability to fly, and long lifespans. In addition, bats have a low incidence of cancer, but the mechanisms underlying this phenomenon remain elusive. Here we discovered that bat cells are more resistant than human
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