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Key Documents

A6733

Sigma-Aldrich

Auranofin

≥98% (HPLC), powder, leukocyte activation pathway inhibitor

Synonyme(s) :

1-Thio-β-D-glucopyranosatotriethylphosphine gold-2,3,4,6-tetraacetate, 3,4,5-Triacetyloxy-6-(acetyloxymethyl) oxane-2-thiolate triethylphosphanium, SKF 39162

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About This Item

Formule empirique (notation de Hill):
C20H34AuO9PS
Numéro CAS:
Poids moléculaire :
678.48
Numéro CE :
Numéro MDL:
Code UNSPSC :
51111800
ID de substance PubChem :
Nomenclature NACRES :
NA.77

product name

Auranofin, ≥98% (HPLC)

Niveau de qualité

Pureté

≥98% (HPLC)

Forme

powder

Solubilité

DMSO: ≥5 mg/mL

Auteur

Prometheus

Température de stockage

room temp

Chaîne SMILES 

CCP(CC)(CC)=[Au]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O

InChI

1S/C14H20O9S.C6H15P.Au/c1-6(15)19-5-10-11(20-7(2)16)12(21-8(3)17)13(14(24)23-10)22-9(4)18;1-4-7(5-2)6-3;/h10-14,24H,5H2,1-4H3;4-6H2,1-3H3;/q;;+1/p-1/t10-,11-,12+,13-,14+;;/m1../s1

Clé InChI

AUJRCFUBUPVWSZ-XTZHGVARSA-M

Application

Auranofin inhibits both leukocyte activation pathways at multiple sites and the release of inflammatory mediators from human macrophages, basophils, and pulmonary mast cells. Auranofin also inhibits 5-lipoxygenase in human neutrophils, IKB kinase (IKK) by modifying Cys-179 of the IKKβ subunit 5 and selenoenzyme thioredoxin reductase (TrxR) which is involved in the defense against oxidative stress. Auranofin is a disease-modifying antirheumatic drug (DMARD) and has been used to study the anti-proliferative effects against OVCAR-3 human ovarian carcinoma cells.

Actions biochimiques/physiologiques

Auranofin inhibits various leukocyte activation pathways at multiple sites. Auranofin inhibits the release of inflammatory mediators from human macrophages, basophils, and pulmonary mast cells. The compound also inhibits 5-lipoxygenase in human neutrophils. Auranofin is a disease-modifying antirheumatic drug (DMARD). The compound is a potent inhibitor of selenoenzyme thioredoxin reductase (TrxR), which is involved in defense against oxidative stress. Auranofin is an efficient inducer of mitochondrial membrane permeability transition pore in the presence of calcium ions related to its inhibition of mitochondrial thioredoxin reductase. Auranofin inhibits IKB kinase (IKK) by modifying Cys-179 of the IKKβ subunit 5.

Caractéristiques et avantages

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

Pictogrammes

Skull and crossbonesHealth hazard

Mention d'avertissement

Danger

Mentions de danger

Classification des risques

Acute Tox. 3 Oral - Repr. 2

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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Consulter la Bibliothèque de documents

Jong-Lyel Roh et al.
Antioxidants & redox signaling, 27(2), 106-114 (2016-10-14)
The glutathione (GSH), thioredoxin (Trx), and Nrf2 systems represent a major defense against reactive oxygen species (ROS), the cellular imbalance of which in cancer promotes growth and therapeutic resistance. This study investigated whether targeting the GSH, Trx, and Nrf2 antioxidant
Samuel Pearson et al.
Chemical communications (Cambridge, England), 48(39), 4695-4697 (2012-04-05)
Polymeric versions of deacetylated auranofin, a gold complex with a sugar ligand, were prepared by post-modifying RAFT glycopolymers. Micellisation of a block copolymer containing pendant Au(I) units produced nanoparticles with an increased anti-proliferative effect against OVCAR-3 human ovarian carcinoma cells.
Lorenzo Turcano et al.
PLoS neglected tropical diseases, 12(11), e0006969-e0006969 (2018-11-27)
Trypanothione reductase (TR) is considered to be one of the best targets to find new drugs against Leishmaniasis. This enzyme is fundamental for parasite survival in the host since it reduces trypanothione, a molecule used by the tryparedoxin/tryparedoxin peroxidase system
David Leitsch
International journal for parasitology. Drugs and drug resistance, 7(3), 321-327 (2017-09-15)
The microaerophilic parasites Entamoeba histolytica, Trichomonas vaginalis, and Giardia lamblia annually cause hundreds of millions of human infections which are treated with antiparasitic drugs. Metronidazole is the most often prescribed drug but also other drugs are in use, and novel
Xiaodong Chen et al.
PloS one, 11(11), e0166386-e0166386 (2016-11-16)
Abnormal survival of retinal pigment epithelium (RPE) cells contributes to the pathogenesis of proliferative vitreoretinopathy (PVR), a sight-threatening disease. In this study, we explored the effect of the anti-rheumatic agent auranofin (AF) on RPE cell survival and studied the underlying

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