ベンズブロマロン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/05/22 09:39:42」(JST)
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Benzbromarone
|
Systematic (IUPAC) name |
(3,5-dibromo-4-hydroxyphenyl)- (2-ethyl-3-benzofuranyl)methanone |
Clinical data |
AHFS/Drugs.com |
International Drug Names |
Identifiers |
CAS Registry Number
|
3562-84-3 N |
ATC code
|
M04AB03 |
PubChem |
CID 2333 |
ChemSpider |
2243 Y |
UNII |
4POG0RL69O Y |
ChEBI |
CHEBI:3023 Y |
ChEMBL |
CHEMBL388590 Y |
Chemical data |
Formula |
C17H12Br2O3 |
Molecular mass
|
424.083 g/mol |
SMILES
- Brc1cc(cc(Br)c1O)C(=O)c2c3ccccc3oc2CC
|
InChI
-
InChI=1S/C17H12Br2O3/c1-2-13-15(10-5-3-4-6-14(10)22-13)16(20)9-7-11(18)17(21)12(19)8-9/h3-8,21H,2H2,1H3 Y
Key:WHQCHUCQKNIQEC-UHFFFAOYSA-N Y
|
Physical data |
Melting point |
161 to 163 °C (322 to 325 °F) |
N (what is this?) (verify) |
Benzbromarone (INN) is a uricosuric agent and non-competitive inhibitor of xanthine oxidase[1] used in the treatment of gout, especially when allopurinol, a first-line treatment, fails or produces intolerable adverse effects. It is structurally related to the antiarrhythmic amiodarone.[2]
Benzbromarone is highly effective and well tolerated,[3][4][5][6] and clinical trials as early as 1981 and as recently as April 2008 have suggested it is superior to both allopurinol, a xanthine oxidase inhibitor but not uricosuric, and probenecid, another uricosuric drug.[7][8]
Contents
- 1 Effect on cytochrome P450
- 2 Safety
- 3 See also
- 4 References
Effect on cytochrome P450
Benzbromarone is a very potent inhibitor of CYP2C9.[2][9] Several analogues of the drug have been developed as CYP2C9 and CYP2C19 inhibitors for use in research.[10][11]
Safety
Benzbromarone was introduced in the 1970s and was viewed as having few associated serious adverse reactions. It was registered in about 20 countries throughout Europe, Asia and South America.
In 2003, the drug was withdrawn by Sanofi-Synthélabo, after reports of serious hepatotoxicity, although it is still marketed in several countries by other drug companies.[12]
See also
References
- ^ Sinclair, DS; Fox, IH (1975). "The pharmacology of hypouricemic effect of benzbromarone". The Journal of rheumatology 2 (4): 437–45. PMID 1206675.
- ^ a b Kumar, V.; Locuson, CW; Sham, YY; Tracy, TS (2006). "Amiodarone Analog-Dependent Effects on CYP2C9-Mediated Metabolism and Kinetic Profiles". Drug Metabolism and Disposition 34 (10): 1688–96. doi:10.1124/dmd.106.010678. PMID 16815961.
- ^ Heel, R.C.; Brogden, R.N.; Speight, T.M.; Avery, G.S. (1977). "Benzbromarone". Drugs 14 (5): 349–66. doi:10.2165/00003495-197714050-00002. PMID 338280.
- ^ Masbernard, A; Giudicelli, CP (1981). "Ten years' experience with benzbromarone in the management of gout and hyperuricaemia" (PDF). South African Medical Journal 59 (20): 701–6. PMID 7221794.
- ^ Perez-Ruiz, F; Alonso-Ruiz, A; Calabozo, M; Herrero-Beites, A; Garcia-Erauskin, G; Ruiz-Lucea, E (1998). "Efficacy of allopurinol and benzbromarone for the control of hyperuricaemia. A pathogenic approach to the treatment of primary chronic gout". Annals of the Rheumatic Diseases 57 (9): 545–9. doi:10.1136/ard.57.9.545. PMC 1752740. PMID 9849314.
- ^ Reinders, Mattheus K.; Roon, Eric N.; Houtman, Pieternella M.; Brouwers, Jacobus R. B. J.; Jansen, Tim L. Th. A. (2007). "Biochemical effectiveness of allopurinol and allopurinol-probenecid in previously benzbromarone-treated gout patients". Clinical Rheumatology 26 (9): 1459–65. doi:10.1007/s10067-006-0528-3. PMID 17308859.
- ^ Schepers, GW (1981). "Benzbromarone therapy in hyperuricaemia; comparison with allopurinol and probenecid". The Journal of International Medical Research 9 (6): 511–5. PMID 7033016.
- ^ Reinders, M K; Van Roon, E N; Jansen, T L T. A; Delsing, J; Griep, E N; Hoekstra, M; Van De Laar, M A F J; Brouwers, J R B J (2008). "Efficacy and tolerability of urate-lowering drugs in gout: A randomised controlled trial of benzbromarone versus probenecid after failure of allopurinol". Annals of the Rheumatic Diseases 68 (1): 51–6. doi:10.1136/ard.2007.083071. PMID 18250112.
- ^ Hummel, M. A. (2005). "CYP2C9 Genotype-Dependent Effects on in Vitro Drug-Drug Interactions: Switching of Benzbromarone Effect from Inhibition to Activation in the CYP2C9.3 Variant". Molecular Pharmacology. doi:10.1124/mol.105.013763.
- ^ Locuson, Charles W.; Rock, Denise A.; Jones, Jeffrey P. (2004). "Quantitative Binding Models for CYP2C9 Based on Benzbromarone Analogues†". Biochemistry 43 (22): 6948–58. doi:10.1021/bi049651o. PMID 15170332.
- ^ Locuson, Charles W.; Suzuki, Hisashi; Rettie, Allan E.; Jones, Jeffrey P. (2004). "Charge and Substituent Effects on Affinity and Metabolism of Benzbromarone-Based CYP2C19 Inhibitors". Journal of Medicinal Chemistry 47 (27): 6768–76. doi:10.1021/jm049605m. PMID 15615526.
- ^ Lee, Ming-Han H; Graham, Garry G; Williams, Kenneth M; Day, Richard O (2008). "A Benefit-Risk Assessment of Benzbromarone in the Treatment of Gout". Drug Safety 31 (8): 643–65. doi:10.2165/00002018-200831080-00002. PMID 18636784.
Drugs used for gout (M04)
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Uricosurics |
- primary: Probenecid
- Sulfinpyrazone
- Benzbromarone
- Isobromindione
- secondary: Amlodipine
- Atorvastatin
- Fenofibrate
- Guaifenesin
- Losartan
|
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Xanthine oxidase inhibitors |
- purine analogues: Allopurinol#
- Oxypurinol
- Tisopurine
other: Febuxostat
- Inositols (Phytic acid
- Myo-inositol)
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Mitotic inhibitors |
|
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Other |
- Cinchophen
- NSAIDs except aspirin
- Sevelamer
- Urate oxidase (Rasburicase
- Pegloticase)
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
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Index of joint
|
|
Description |
- Anatomy
- head and neck
- cranial
- arms
- torso and pelvis
- legs
- bursae and sheathes
- Physiology
|
|
Disease |
- Arthritis
- acquired
- back
- childhood
- soft tissue
- Congenital
- Injury
- Symptoms and signs
- Examination
|
|
Treatment |
- Procedures
- Drugs
- rheumatoid arthritis
- gout
- topical analgesics
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|
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UpToDate Contents
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English Journal
- Dubost JJ, Mathieu S, Soubrier M.SourceService de rhumatologie, hôpital G. Montpied, CHU, BP 69, 63003 Clermont-Ferrand cedex 1, France.
- La Revue de médecine interne / fondée ... par la Société nationale francaise de médecine interne.Rev Med Interne.2011 Dec;32(12):751-7. Epub 2011 Mar 5.
- In France, colchicine remains the standard treatment for the acute flare of gout. The lowest dose currently used decreases digestive toxicity. Doses of colchicine should be adapted to renal function and age, and possible drug interactions should be considered. Non steroidal anti-inflammatory drugs a
- PMID 21382654
- Use of Uric Acid-Lowering Agents Limits Experimental Cyclosporine Nephropathy.
- Mazali FC, Johnson RJ, Mazzali M.SourceDivision of Nephrology, School of Medical Sciences, State University of Campinas, UNICAMP, Campinas, Brazil.
- Nephron. Experimental nephrology.Nephron Exp Nephrol.2011 Nov 25;120(1):e12-e19. [Epub ahead of print]
- Background: Hyperuricemia frequently complicates cyclosporine (CsA) therapy. Previous studies have shown that hyperuricemia exacerbates interstitial and vascular lesions in the cyclosporine model. We tested the hypothesis that normalization of uric acid could prevent the development of cyclosporine
- PMID 22126908
Japanese Journal
- ジェネリック医薬品"ベンズブロマロン錠"の高尿酸血症患者の腎機能に及ぼす影響 : 年齢と投与量による変化
- 痛風患者におけるbenzbromarone投与のCRPに対する影響
Related Links
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- ベンズブロマロン(Benzbromarone)の検索ならお薬検索QLife(キューライフ)。お医者さんが処方する処方薬と、薬局で買える市販薬(OTC)、の効果と副作用、写真、添付文書、保管方法等を掲載。商品名だけでなく一般名や剤形、色などから ...
Related Pictures
★リンクテーブル★
[★]
- 英
- pharmacology
- 関
- drug entries
定義
- 生物系と化学物質の選択的な相互作用を研究する学問 (SPC.2)
生物系と薬の相互作用
- 薬の生物系に対する相互作用:薬理作用 <-化学の視点
- 生物系の薬に対する相互作用:薬物動態 <-生物の視点
関連分野
- 薬物学 materia medica
- 生薬学
- 実験薬理学
- 臨床薬理学
- 動物薬理学
- 人体薬理学
- 比較薬理学
- 薬理作用学(薬力学)
- 薬物動態学
- 中毒学、毒科学
- 薬物治療学
- 処方学
薬品の命名
薬一覧
薬理動態
神経伝達物質
神経筋接合部遮断薬(筋弛緩薬)
交感神経作動薬
- →アドレナリン受容体
交感神経遮断薬
- →アドレナリン受容体
副交感神経作動薬
- →アセチルコリン受容体
副交感神経遮断薬
- →アセチルコリン受容体
甲状腺関連物質
[★]
- 英
- benzbromarone
- 商
- ウロリープ、ガウトマロン、キランガ、トレビアノーム、ナーカリシン、ブロマノーム、ベンズマロン、ムイロジン、ユリノーム
- 関
- 痛風、尿酸、痛風治療薬、薬理学
概念
作用機序
注意
- ①尿量を多くする ← 水を飲む
- ②尿アルカリ化薬(ウラリット)併用 尿のpHを6.0-7.0に維持
- ①投与半年は定期的に肝機能の検査
- ②眼球結膜黄染、尿濃染出現で停止
禁忌
- 1. 肝障害の徴候が見られた場合
- 2. 腎結石・高度の腎機能障害
- 3. 薬剤過敏症
- 4. 妊婦又は妊娠の可能性
[★]
- 英
- arthrifuge, gout suppressant, drug for treatment of gout, antipodagric
- 同
- 抗痛風薬
- 関
- 薬理学、痛風