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Auranofin is a gold complex classified by the World Health Organization as an antirheumatic agent. It has the brand name Ridaura.

Use

Auranofin is used to treat rheumatoid arthritis. It improves arthritis symptoms including painful or tender and swollen joints and morning stiffness.^[3]

Research

HIV infection

Auranofin is under investigation as means of reducing the viral reservoir of HIV that lies latent in the body's T-cells despite treatment with antiretroviral therapy. ^[4]

Amebiasis

Auranofin has been identified in a high-throughput drug screen as 10 times more potent than metronidazole on Entamoeba histolytica, the protozoan agent of human amebiasis. Assays of thioredoxin reductase and transcriptional profiling suggest that the effect of auranofin on the enzyme enhances the sensitivity of the trophozoites to reactive oxygen-mediated killing in mouse and hamster models; the results are markedly reductions of the number of parasites, the inflammatory reaction to the infestation and the damage to the liver.^[5]^[6]^[7]

References

^ ^a ^b ^c ^d Kean, WF; Hart, L; Buchanan, WW (May 1997). "Auranofin." (PDF). British Journal of Rheumatology 36 (5): 560–72. doi:10.1093/rheumatology/36.5.560. PMID 9189058.
^ ^a ^b ^c ^d "Ridaura (auranofin) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Retrieved 13 March 2014.
^ MedlinePlus DrugInfo medmaster-a685038
^ Gold-based drug shows promise in clearing HIV reservoir in monkey study. Keith Alcorn. AIDSmaps.com. Accessed 23 April 2011.
^ Debnath, Anjan; Parsonage, Derek; Andrade, Rosa M; He, Chen; Cobo, Eduardo R; Hirata, Ken; Chen, Steven; García-Rivera, Guillermina; Orozco, Esther; Martínez, Máximo B; Gunatilleke, Shamila S; Barrios, Amy M; Arkin, Michelle R; Poole, Leslie B; McKerrow, James H; Reed, Sharon L (2012). "A high-throughput drug screen for Entamoeba histolytica identifies a new lead and target". Nature Medicine 18 (6): 956. doi:10.1038/nm.2758. PMID 22610278.
^ Drug Found for Parasite That Is Major Cause of Death Worldwide
^ Arthritis Drug Effective Against Global Parasite, Study Suggests

External links

MedlinePlus DrugInfo medmaster-a685038

UpToDate Contents

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1. リウマチ性疾患への金化合物の使用 use of gold compounds in rheumatic diseases
2. 金治療の主な副作用 major side effects of gold therapy
3. 膜性腎症の原因および診断 causes and diagnosis of membranous nephropathy
4. 喘息治療の代替剤および経験的薬剤 alternative and experimental agents for the treatment of asthma
5. 関節リウマチ患者における腎疾患 renal disease in patients with rheumatoid arthritis

English Journal

Pinacidil protects osteoblastic cells against antimycin A-induced oxidative damage.

Choi EM1, Jung WW2, Suh KS3.
Molecular medicine reports.Mol Med Rep.2015 Jan;11(1):746-52. doi: 10.3892/mmr.2014.2721. Epub 2014 Oct 21.
The present study aimed to investigate the protective effect of a non-selective mitochondrial adenosine triphosphate (ATP)-sensitive potassium channel (mito-KATP) opener, pinacidil, on antimycin A-induced oxidative damage in osteoblastic MC3T3-E1 cells. Antimycin A inhibits mitochondrial electron
PMID 25334089

Auranofin, an anti-rheumatic gold compound, modulates apoptosis by elevating the intracellular calcium concentration ([ca2+]I) in mcf-7 breast cancer cells.

Varghese E1, Büsselberg D2.
Cancers.Cancers (Basel).2014 Nov 6;6(4):2243-58. doi: 10.3390/cancers6042243.
Auranofin, a transition metal complex is used for the treatment of rheumatoid arthritis but is also an effective anti-cancer drug. We investigate the effects of Auranofin in inducing cell death by apoptosis and whether these changes are correlated to changes of intracellular calcium concentration ([
PMID 25383481

Auranofin induces apoptosis and necrosis in HeLa cells via oxidative stress and glutathione depletion.

You BR, Shin HR, Han BR, Kim SH, Park WH.
Molecular medicine reports.Mol Med Rep.2014 Oct 31. doi: 10.3892/mmr.2014.2830. [Epub ahead of print]
Auranofin (Au), an inhibitor of thioredoxin reductase, is a known anti‑cancer drug. In the present study, the anti‑growth effect of Au on HeLa cervical cancer cells was examined in association with levels of reactive oxygen species (ROS) and glutathione (GSH). Au inhibited the growth of HeLa cel
PMID 25370167

Japanese Journal

ブシラミンと金製剤 (特集膠原病・リウマチ性疾患の治療の現状と展望) -- (免疫抑制薬・抗リウマチ薬)

伊藤聡
日本内科学会雑誌 100(10), 2936-2941, 2011-10-10
NAID 40019038630

Auranofin protects against cocaine-induced hepatic injury through induction of heme oxygenase-1

ASHINO Takashi,SUGIUCHI Jinko,UEHARA Junna,NAITO YAMAMOTO Yumiko,KENMOTSU Sachiyo,IWAKURA Yoichiro,SHIODA Seiji,NUMAZAWA Satoshi,YOSHIDA Takemi
Journal of toxicological sciences 36(5), 635-643, 2011-10-01
… Auranofin, a disease-modifying gold compound, has been empirically applying to the management of rheumatoid arthritis. … We investigated a protective effect of auranofin against hepatic injury induced by cocaine. … Auranofin (10 mg/ml, i.p.) significantly induced hepatic HO-1 protein in mice from 12 hr after treatment. … Interestingly, pretreatment with auranofin resulted in the prevention of the increase of serum ALT and AST activities in a dose-dependent manner. …
NAID 10029481491

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リンク元

「オーラノフィン」

Auranofin
Systematic (IUPAC) name
	gold(+1) cation; 3,4,5-triacetyloxy-6- (acetyloxymethyl) oxane-2-thiolate; triethylphosphanium
Clinical data
Trade names	Ridaura
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a685038
Pregnancy cat.	B3 (AU) C (US)
Legal status	Prescription Only (S4) (AU) POM (UK) ℞-only (US)
Routes	Oral
Pharmacokinetic data
Bioavailability	40%
Protein binding	60%
Metabolism	Plasma membrane of the cell removes the acetyl groups of the glucose moiety.
Half-life	21-31 hours
Excretion	Urine (60%), faeces
Identifiers
CAS number	34031-32-8
ATC code	M01CB03
PubChem	CID 6333901
DrugBank	DB00995
ChemSpider	21229878
UNII	3H04W2810V
KEGG	D00237
ChEBI	CHEBI:2922
ChEMBL	CHEMBL1366
Chemical data
Formula	C20H35AuO9PS+
Mol. mass	679.493 g/mol
	SMILES CC(=O)O[C@H]1O[C@@H](S[Au]P(CC)(CC)CC)[C@H](OC(C)=O)[C@@H](OC(C)=O)C1OC(C)=O;
	InChI InChI=1S/C13H18O9S.C6H15P.Au/c1-5(14)18-9-10(19-6(2)15)12(21-8(4)17)22-13(23)11(9)20-7(3)16;1-4-7(5-2)6-3;/h9-13,23H,1-4H3;4-6H2,1-3H3;/t9-,10?,11+,12-,13-;;/m0../s1 ; Key:JCUNAWURTWIACY-YHEXQHTOSA-N ;
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　　[★]

英: auranofin
商: リドーラ Ridaura、グレリース)、リザスト
関: 抗リウマチ薬

[kin-1] Kean, WF; Hart, L; Buchanan, WW (May 1997). "Auranofin." (PDF). British Journal of Rheumatology 36 (5): 560–72. doi:10.1093/rheumatology/36.5.560. PMID 9189058.

[MSR-2] "Ridaura (auranofin) dosing, indications, interactions, adverse effects, and more". Medscape Reference. WebMD. Retrieved 13 March 2014.

[3] MedlinePlus DrugInfo medmaster-a685038

[4] Gold-based drug shows promise in clearing HIV reservoir in monkey study. Keith Alcorn. AIDSmaps.com. Accessed 23 April 2011.

[5] Debnath, Anjan; Parsonage, Derek; Andrade, Rosa M; He, Chen; Cobo, Eduardo R; Hirata, Ken; Chen, Steven; García-Rivera, Guillermina; Orozco, Esther; Martínez, Máximo B; Gunatilleke, Shamila S; Barrios, Amy M; Arkin, Michelle R; Poole, Leslie B; McKerrow, James H; Reed, Sharon L (2012). "A high-throughput drug screen for Entamoeba histolytica identifies a new lead and target". Nature Medicine 18 (6): 956. doi:10.1038/nm.2758. PMID 22610278.

[6] Drug Found for Parasite That Is Major Cause of Death Worldwide

[7] Arthritis Drug Effective Against Global Parasite, Study Suggests

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auranofin