CAS 34031-32-8|auranofin

Introduction：Basic information about CAS 34031-32-8|auranofin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Common Nameauranofin
CAS Number34031-32-8Molecular Weight680.50
Density/Boiling Point425.5ºC at 760mmHg
Molecular FormulaC20H36AuO9PSMelting Point103 - 105ºC
MSDSChineseUSAFlash Point298ºC

Names

Nameauranofin
SynonymMore Synonyms

auranofin BiologicalActivity

DescriptionAuranofin (SKF-39162) is a thioredoxin reductase (TrxR) inhibitor with an IC50 of 0.2 μM.
Related CatalogSignaling Pathways >>Others >>OthersResearch Areas >>Inflammation/Immunology
Target

IC50: 0.2 μM (TrxR)[1]

In VitroAuranofin is a drug that is approved for the treatment of rheumatoid arthritis but is being investigated for potential therapeutic application in a number of other diseases including cancer, neurodegenerative disorders. Auranofin induces apoptosis in cells through a Bax/Bak-dependent mechanism associated with selective disruption of mitochondrial redox homeostasis in conjunction with oxidation of Prx3[1]. Auranofin inhibits proliferation and survival of SKOV3 cells in a dose- and time-dependent manner. Auranofin treatment activates the pro-apoptotic caspase-3, increases protein levels of apoptosis-inducing proteins Bax and Bim and reduces the expression of the anti-apoptotic mediator Bcl-2 in SKOV3 cells[2]. Auranofin is a lipophilic gold compound with anti-inflammatory and immunosuppressive properties. Auranofin inhibits the cell growth and induction of mitochondrial apoptosis in PC3 human prostate cancer cells. Treatment with auranofin significantly inhibits cell viability with an IC50 value of 2.5 μM after 24 h[3].
In VivoProphylactic treatment of adjuvant-induced arthritis rats with auranofin results in a slight reduction in paw edema, a complete normalization of the depressed IL-2 production, and a reduction of the elevated IL-1 production, but has no effect on the depressed IL-3 production[4].
Cell AssayAuranofin is dissolved in DMSO. Cells are treated with auranofin (0, 50, 100, 200 and 400 nM) for 72 h for the dose-dependent response assay and 100 nM of auranofin is added into the wells for 0, 24, 72 and 120 h for the time-dependent response assay. Control cultures are treated with DMSO. Cell viability is measured by the MTT assay[2].
Animal AdminRats: Prophylactically, auranofin (6.7 to 15 mg of gold/kg), indomethacin (2 mg/kg) or tragacanth vehicle control were administered orally at daily intervals beginning on the day of adjuvant injection. On days 16 to 17 peritoneal exudate cells or spleen cells from normal or adjuvant-injected rats were isolated and tested[4].
References

[1]. Cox AG, et al. The thioredoxin reductase inhibitor auranofin triggers apoptosis through a Bax/Bak-dependent process that involves peroxiredoxin 3 oxidation. Biochem Pharmacol. 2008 Oct 30;76(9):1097-109.

[2]. Park SH, et al. Auranofin displays anticancer activity against ovarian cancer cells through FOXO3 activation independent of p53. Int J Oncol. 2014 Oct;45(4):1691-8.

[3]. Park N, et al. Auranofin promotes mitochondrial apoptosis by inducing annexin A5 expression and translocation in human prostate cancer cells. J Toxicol Environ Health A. 2014;77(22-24):1467-76.

[4]. Lee JC, et al. Effect of auranofin treatment on aberrant splenic interleukin production in adjuvant arthritic rats. J Immunol. 1987 Nov 15;139(10):3268-74.

Chemical & Physical Properties

Boiling Point425.5ºC at 760mmHg
Melting Point103 - 105ºC
Molecular FormulaC20H36AuO9PS
Molecular Weight680.50
Flash Point298ºC
PSA149.54000
LogP2.79250
Water SolubilityDMSO: ≥5mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MD6500000
CHEMICAL NAME :
Gold, (1-thio-beta-D-glucopyranosato-S)(triethylphosphine)- , 2,3,4,6-tetraacetate
CAS REGISTRY NUMBER :
34031-32-8
LAST UPDATED :
199112
DATA ITEMS CITED :
15
MOLECULAR FORMULA :
C20-H34-Au-O9-P-S
MOLECULAR WEIGHT :
678.54

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
1200 ug/kg/2W-I
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from stomach
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
5400 ug/kg/10D-I
TOXIC EFFECTS :
Behavioral - toxic psychosis Behavioral - muscle weakness Behavioral - muscle contraction or spasticity
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
265 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
25500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
235 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
39 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
84940 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
33800 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
53600 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
22600 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
3200 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
100 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
358 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
179 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

MUTATION DATA

TYPE OF TEST :
DNA inhibition
TEST SYSTEM :
Human Cells - not otherwise specified
DOSE/DURATION :
41 umol/L
REFERENCE :
BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 34,3243,1985

Safety Information

Hazard CodesXn
Risk Phrases63-22
Safety Phrases36/37
RIDADRUN 2811 6.1 / PGIII
RTECSMD6500000

Synonyms

(2,3,4,6-tetra-O-acetyl-1-thio-β-L-glucopyranosato-κS)(triethyl-λ-phosphanylidene)gold
auranofin
ridaura
AURANOFINE
Crisinor
Gold, (β-L-glucopyranosato-κS, 1-thio-, 2,3,4,6-tetraacetate)(triethylphosphoranylidene)-
Adtil
EINECS 251-801-9
(2,3,4,6-Tetra-O-acetyl-1-thio-β-L-glucopyranosato-κS)(triethylphosphoranylidene)gold
Crisofin
Ridauran
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