The stability of this product in solution has not been determined. However, various sources report that stock solution are stable for up to 3 months when stored in aliquots at -20°C. This information has not been validated.
A6733
Auranofin
≥98% (HPLC), powder, leukocyte activation pathway inhibitor
Synonym(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
Empirical Formula (Hill Notation):
C20H34AuO9PS
CAS Number:
Molecular Weight:
678.48
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
51111800
EC Number:
251-801-9
MDL number:
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Product Name
Auranofin, ≥98% (HPLC)
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
InChI key
AUJRCFUBUPVWSZ-XTZHGVARSA-M
SMILES string
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
assay
≥98% (HPLC)
form
powder
solubility
DMSO: ≥5 mg/mL
originator
Prometheus
storage temp.
room temp
Quality Level
Related Categories
1 of 4
This Item | SML0493 | SML1296 | PZ0299 |
|---|---|---|---|
| assay ≥98% (HPLC) | assay ≥95% (HPLC) | assay ≥97% (HPLC) | assay ≥98% (HPLC) |
| form powder | form powder | form powder | form powder |
| Quality Level 100 | Quality Level 100 | Quality Level 100 | Quality Level 100 |
| storage temp. room temp | storage temp. room temp | storage temp. −20°C | storage temp. room temp |
| solubility DMSO: ≥5 mg/mL | solubility DMSO: 5 mg/mL, clear (warmed) | solubility DMSO: 5 mg/mL, clear (warmed) | solubility DMSO: 5 mg/mL, clear (warmed) |
| originator Prometheus | originator - | originator - | originator - |
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.
Biochem/physiol Actions
Auranofin inhibits various leukocyte activation pathways at multiple sites and is a disease-modifying antirheumatic drug (DMARD).
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.
Features and Benefits
This compound was developed by Prometheus. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral - Repr. 2
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
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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
Julia Sajman et al.
Scientific reports, 7(1), 11350-11350 (2017-09-14)
The secretory signal elicited by membrane depolarization traverses from the Ca
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.
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
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
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How long can auranofin aliquots in DMSO be stored in -20C?
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