C3662

Cyclosporin A

Name: Cyclosporin A
Brand: SIGMA

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

Synonyme(s) :

Antibiotic S 7481F1, Cyclosporine

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About This Item

Formule empirique (notation de Hill) :

C₆₂H₁₁₁N₁₁O₁₂

Numéro CAS:

59865-13-3

Poids moléculaire :

1202.61

NACRES:

NA.77

PubChem Substance ID:

24278028

UNSPSC Code:

12352200

MDL number:

MFCD00274558

Beilstein/REAXYS Number:

3647785

Nom du produit

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

color

white

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

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 key

PMATZTZNYRCHOR-CGLBZJNRSA-N

biological source

Tolypocladium inflatum

assay

≥95% (HPLC)

form

solid

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

Quality Level

300

Gene Information

human ... PPIA(5478), PPP3CA(5530), PPP3CB(5532), PPP3CC(5533), PPP3R1(5534), PPP3R2(5535)

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Catégories apparentées

Bioactive Small Molecules

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

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

Classe de stockage

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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Consulter la Bibliothèque de documents

Loss of vacuolar-type H+-ATPase induces caspase-independent necrosis-like death of hair cells in zebrafish neuromasts.

Peu Santra et al.

Disease models & mechanisms, 14(7) (2021-07-24)

The vacuolar-type H+-ATPase (V-ATPase) is a multi-subunit proton pump that regulates cellular pH. V-ATPase activity modulates several cellular processes, but cell-type-specific functions remain poorly understood. Patients with mutations in specific V-ATPase subunits can develop sensorineural deafness, but the underlying mechanisms

Discovery of 7-N-piperazinylthiazolo[5,4-d]pyrimidine analogues as a novel class of immunosuppressive agents with in vivo biological activity.

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

Functionalized chalcones as selective inhibitors of P-glycoprotein and breast cancer resistance protein.

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

Debio 025, a cyclophilin binding molecule, is highly efficient in clearing hepatitis C virus (HCV) replicon-containing cells when used alone or in combination with specifically targeted antiviral therapy for HCV (STAT-C) inhibitors.

Lotte Coelmont et al.

Antimicrobial agents and chemotherapy, 53(3), 967-976 (2008-12-24)

Debio 025 is a potent inhibitor of hepatitis C virus (HCV) replication (J. Paeshuyse et al., Hepatology 43:761-770, 2006). In phase I clinical studies, monotherapy (a Debio 025 dose of 1,200 mg twice a day) resulted in a mean maximal

Comparative in vitro anti-hepatitis C virus activities of a selected series of polymerase, protease, and helicase inhibitors.

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

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