オーラノフィン。リドーラ
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/02/18 09:26:35」(JST)
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Auranofin
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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. |
C (US) |
Legal status |
℞-only (US) |
Routes |
Oral |
Identifiers |
CAS number |
34031-32-8 Y |
ATC code |
M01CB03 |
PubChem |
CID 6333901 |
DrugBank |
DB00995 |
ChemSpider |
21229878 Y |
UNII |
3H04W2810V Y |
KEGG |
D00237 Y |
ChEBI |
CHEBI:2922 N |
ChEMBL |
CHEMBL1366 N |
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
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InChI
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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 Y
Key:JCUNAWURTWIACY-YHEXQHTOSA-N Y
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N (what is this?) (verify) |
Auranofin is a gold complex classified by the World Health Organization as an antirheumatic agent. It has the brand name Ridaura.
Contents
- 1 Use
- 2 Research
- 2.1 HIV infection
- 2.2 Amebiasis
- 3 References
- 4 Further reading
- 5 External links
Use[edit]
Auranofin is used to treat rheumatoid arthritis. It improves arthritis symptoms including painful or tender and swollen joints and morning stiffness.[1]
Research[edit]
HIV infection[edit]
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. [2]
Amebiasis[edit]
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.[3][4][5]
References[edit]
- ^ 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 et al. (2012). "A high-throughput drug screen for Entamoeba histolytica identifies a new lead and target". Nature Medicine. doi:10.1038/nm.2758.
- ^ Drug Found for Parasite That Is Major Cause of Death Worldwide
- ^ Arthritis Drug Effective Against Global Parasite, Study Suggests
Further reading[edit]
- Jeon K, Byun M, Jue D (2003). "Gold compound auranofin inhibits IkappaB kinase (IKK) by modifying Cys-179 of IKKbeta subunit". Exp Mol Med 35 (2): 61–6. PMID 12754408.
- Kim I, Jin J, Lee I, Park S (2004). "Auranofin induces apoptosis and when combined with retinoic acid enhances differentiation of acute promyelocytic leukaemia cells in vitro". Br J Pharmacol 142 (4): 749–55. doi:10.1038/sj.bjp.0705708. PMC 1575039. PMID 15159275.
- Venardos K, Harrison G, Headrick J, Perkins A (2004). "Auranofin increases apoptosis and ischaemia-reperfusion injury in the rat isolated heart". Clin Exp Pharmacol Physiol 31 (5–6): 289–94. doi:10.1111/j.1440-1681.2004.03993.x. PMID 15191400.
- Hafejee A, Winhoven S, Coulson I (2004). "Jessner's lymphocytic infiltrate responding to oral auranofin". J Dermatolog Treat 15 (5): 331–2. doi:10.1080/09546630410016924. PMID 15370403.
- Rigobello M, Folda A, Baldoin M, Scutari G, Bindoli A (2005). "Effect of auranofin on the mitochondrial generation of hydrogen peroxide. Role of thioredoxin reductase". Free Radic Res 39 (7): 687–95. doi:10.1080/10715760500135391. PMID 16036347.
- Suarez-Almazor ME, Spooner CH, Belseck E, Shea B (2000). "Auranofin versus placebo in rheumatoid arthritis". In Suarez-Almazor, Maria E. Cochrane Database Syst Rev (2): CD002048. doi:10.1002/14651858.CD002048. PMID 10796461.
External links[edit]
- MedlinePlus DrugInfo medmaster-a685038
Specific antirheumatic products / DMARDs (M01C)
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Quinolines |
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Gold preparations |
- Sodium aurothiomalate
- Sodium aurothiosulfate
- Auranofin
- Aurothioglucose
- Aurotioprol
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Other |
- Penicillamine #/Bucillamine
- Chloroquine #/Hydroxychloroquine
- Leflunomide
- Sulfasalazine #
- antifolate (Methotrexate #)
- thiopurine (Azathioprine) #
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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noco (arth/defr/back/soft)/cong, sysi/epon, injr
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Gold compounds
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Gold(-I) |
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Gold(I) |
- AuBr
- AuCl
- AuI
- AuOH
- Au2S
- (C2H5)3PAuSC5H5O(CO2CH3)3CH2OCOCH3
- AuSC5H5O(OH)3CH2OH
- NaAuSCH2CHOHCH2SO3
- BrAuSC4H8
- ClAuSC4H8
- ClAuS(CH3)2
- ClAuP(C6H5)3
- Na2AuSCHCO2CH2CO2
- NaAuSCHCO2CH2CO2H
- Na3Au(S2O3)2
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Gold(II) |
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Gold(I,III) |
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Gold(III) |
- HAuCl4
- HAuBr4
- AuBr3
- AuCl3
- AuF3
- Au2O3
- Au(OH)3
- Au2S3
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Gold(V) |
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UpToDate Contents
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English Journal
- Fourier Transform Infrared spectroscopy discloses different types of cell death in flow cytometrically sorted cells.
- Le Roux K1, Prinsloo LC2, Meyer D3.
- Toxicology in vitro : an international journal published in association with BIBRA.Toxicol In Vitro.2015 Aug 4. pii: S0887-2333(15)00187-3. doi: 10.1016/j.tiv.2015.08.002. [Epub ahead of print]
- Fourier Transform Infrared (FTIR) spectroscopy is a label free methodology showing promise in characterizing different types of cell death. Cervical adenocarcinoma (HeLa) and African monkey kidney (Vero) cells were treated with a necrosis inducer (methanol), novel apoptotic inducers (diphenylphosphi
- PMID 26254093
- The effect of 1:2 Ag(I) thiocyanate complexes in MCF-7 breast cancer cells.
- Ferreira E1, Munyaneza A, Omondi B, Meijboom R, Cronjé MJ.
- Biometals : an international journal on the role of metal ions in biology, biochemistry, and medicine.Biometals.2015 Aug;28(4):765-81. doi: 10.1007/s10534-015-9865-5. Epub 2015 Jun 7.
- There is much interest currently in the design of metal compounds as drugs and various metal compounds are already in clinical use. These include gold(I) compounds such as auranofin and the anti-cancer platinum(II) complex, cisplatin. Bis-chelated gold(I) phosphine complexes have also shown great po
- PMID 26049979
- Evidence that the antiproliferative effects of auranofin in Saccharomyces cerevisiae arise from inhibition of mitochondrial respiration.
- Gamberi T1, Fiaschi T1, Modesti A1, Massai L2, Messori L2, Balzi M1, Magherini F3.
- The international journal of biochemistry & cell biology.Int J Biochem Cell Biol.2015 Aug;65:61-71. doi: 10.1016/j.biocel.2015.05.016. Epub 2015 May 27.
- Auranofin is a gold based drug in clinical use since 1985 for the treatment of rheumatoid arthritis. Beyond its antinflammatory properties, auranofin exhibits other attractive biological and pharmacological actions such as a potent in vitro cytotoxicity and relevant antimicrobial and antiparasitic e
- PMID 26024642
Japanese Journal
- Experimental induction of heterotopic bone in abdominal implants
- ASCENCIO DANIEL,HERNANDEZ-PANDO ROGELIO,BARRIOS JORGE,SORIANO ROSA EUGENIA,PEREZ-GUILLE BEATRIZ,VILLEGAS FERNANDO,RIDAURA SANZ CECILIA,LOPEZ-CORELLA EDUARDO,CARRASCO DANIEL,FRENK F. SILVESTRE
- Wound repair and regeneration 12(6), 643-649, 2004-11-01
- NAID 10020396553
- Progressive paralysis associated with diffuse astrocyte anaplasia in Δ202 mice homozygous for a transgene encoding the SV40 T antigen
- LOPEZ-REVILLA Ruben,SOTO-ZARATE Carlos,RIDAURA Cecilia,CHAVEZ-DUENAS Lucia,PAUL Dieter
- Neuropathology : official journal the Japanese Society of Neuropathology 24(1), 30-37, 2004-03-01
- NAID 10014201041
Related Links
- Ridaura official prescribing information for healthcare professionals. Includes: indications, dosage, adverse reactions, pharmacology and more. ... Pharmacokinetics: Pharmacokinetic studies were performed in rheumatoid arthritis ...
- Ridaura - Get up-to-date information on Ridaura side effects, uses, dosage, overdose, pregnancy, alcohol and more. Learn more about Ridaura ... Serious side effects have been reported with Ridaura. See the “Ridaura Precautions ...
Related Pictures
★リンクテーブル★
[★]
- 英
- auranofin
- 商
- リドーラ Ridaura、グレリース)、リザスト
- 関
- 抗リウマチ薬