Benzbromarone (BioDeep_00000017954)

   

human metabolite Chemicals and Drugs


代谢物信息卡片


(3,5-Dibromo-4-hydroxyphenyl)(2-ethyl-1-benzofuran-3-yl)methanone

化学式: C17H12Br2O3 (421.9153122)
中文名称: 苯溴马隆
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCC1=C(C(=O)C2=CC(Br)=C(O)C(Br)=C2)C2=CC=CC=C2O1
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

描述信息

Benzbromarone (INN) is a uricosuric agent 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. Benzbromarone is a very potent inhibitor of CYP2C9. Several analogues of the drug have been developed as CYP2C9 and CYP2C19 inhibitors for use in research.
M - Musculo-skeletal system > M04 - Antigout preparations > M04A - Antigout preparations > M04AB - Preparations increasing uric acid excretion
D018501 - Antirheumatic Agents > D006074 - Gout Suppressants > D014528 - Uricosuric Agents
C26170 - Protective Agent > C921 - Uricosuric Agent

同义名列表

35 个代谢物同义名

(3,5-Dibromo-4-hydroxyphenyl)(2-ethyl-1-benzofuran-3-yl)methanone; Ketone, 3,5-dibromo-4-hydroxyphenyl 2-ethyl-3-benzofuranyl; 3, 5-Dibromo-4-hydroxyphenyl-2-ethyl-3-benzofuranyl ketone; 3,5-Dibromo-4-hydroxyphenyl-2-ethyl-3-benzofuranyl ketone; 2,6-dibromo-4-(2-ethyl-1-benzofuran-3-carbonyl)phenol; 2-Ethyl-3-(3,5-dibrom-4-hydroxybenzoyl)benzofuran; Sanofi winthrop brand OF benzbromarone; Ratiopharm brand OF benzbromarone; Benzbromarone ratiopharm brand; Heumann brand OF benzbromarone; Sanfer brand OF benzbromarone; Aliud brand OF benzbromarone; Benzbromarone heumann brand; Benzbromarone sanfer brand; Benzbromarone aliud brand; Benzbromaron-ratiopharm; Benzbromaron ratiopharm; Benzbromaronratiopharm; Benzbromarone(usan); AL, benzbromaron; Benzbromaron al; benzbromarone; Benzbromaron; L 2214-Labaz; Narcaricin; Acifugan; Uricovac; Normurat; Besuric; Urinorm; Minuric; Hipurik; Uroleap; Desuric; Exurate



数据库引用编号

10 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:

  • PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。



文献列表

  • C-Q Yan, C Liang, Z-R Lan, C Su, S-Y Xiong, Y-X Yang, J-M Chen, S-L Tang, J-S Huang, Z-H Zhang, M-J Luo, Z-H Xiao. Comparison of the efficacy of febuxostat vs. benzbromarone in the treatment of gout: a meta-analysis in Chinese gout patients. European review for medical and pharmacological sciences. 2023 Dec; 27(24):11988-12003. doi: 10.26355/eurrev_202312_34797. [PMID: 38164861]
  • Yanfen Niu, Qiang Li, Caixia Tu, Na Li, Lihui Gao, Hua Lin, Zhenyu Wang, Zhihong Zhou, Ling Li. Hypouricemic Actions of the Pericarp of Mangosteen in Vitro and in Vivo. Journal of natural products. 2023 01; 86(1):24-33. doi: 10.1021/acs.jnatprod.2c00531. [PMID: 36634312]
  • Yu-Kai Zhang, Jia-Shu Chen, Min-Min Wang, Chuan-Zeng Wang, Mu-Xuan Wang, Zhen Wang, Qin-Liang Yang, Bin Sun, Jin-Yue Sun, Yu-Fa Liu, Chao Liu. Synthesis and bioactivity evaluation of novel nuciferine derivatives with antihyperuricemia and nephroprotective effects. Bioorganic chemistry. 2022 09; 126(?):105916. doi: 10.1016/j.bioorg.2022.105916. [PMID: 35687986]
  • Xizi Liu, Shiyi Han, Qian Yang, Siyang Fan. Beneficial herb-drug interaction of Gnaphalium affine extract on benzbromarone: A pharmacokinetic and pharmacodynamic study in rats. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2022 Jul; 102(?):154203. doi: 10.1016/j.phymed.2022.154203. [PMID: 35660349]
  • Dongmei Liu, Binbin Zhou, Zhen Li, Zhuojun Zhang, Xiaojuan Dai, Zongfei Ji, Huiyong Chen, Ying Sun, Lindi Jiang. Effectiveness of benzbromarone versus febuxostat in gouty patients: a retrospective study. Clinical rheumatology. 2022 Jul; 41(7):2121-2128. doi: 10.1007/s10067-022-06110-5. [PMID: 35229198]
  • Somdutt Mujwar, Avanish Tripathi. Repurposing benzbromarone as antifolate to develop novel antifungal therapy for Candida albicans. Journal of molecular modeling. 2022 Jun; 28(7):193. doi: 10.1007/s00894-022-05185-w. [PMID: 35716240]
  • Danii L S Suijk, Michaël J B van Baar, Erik J M van Bommel, Zainab Iqbal, Merle M Krebber, Volker Vallon, Daan Touw, Ewout J Hoorn, Max Nieuwdorp, Mark M H Kramer, Jaap A Joles, Petter Bjornstad, Daniël H van Raalte. SGLT2 Inhibition and Uric Acid Excretion in Patients with Type 2 Diabetes and Normal Kidney Function. Clinical journal of the American Society of Nephrology : CJASN. 2022 05; 17(5):663-671. doi: 10.2215/cjn.11480821. [PMID: 35322793]
  • Young Ho Lee, Gwan Gyu Song. Comparative efficacy and safety of dotinurad, febuxostat, and benzbromarone in hyperuricemic patients with or without gout: A network meta-analysis of randomized controlled trials. International journal of clinical pharmacology and therapeutics. 2022 Mar; 60(3):159-166. doi: 10.5414/cp204097. [PMID: 34779393]
  • Xiaomei Xue, Zhen Liu, Xinde Li, Jie Lu, Can Wang, Xuefeng Wang, Wei Ren, Ruixia Sun, Zhaotong Jia, Xiaopeng Ji, Ying Chen, Yuwei He, Aichang Ji, Wenyan Sun, Hui Zhang, Tony R Merriman, Changgui Li, Lingling Cui. The efficacy and safety of citrate mixture vs sodium bicarbonate on urine alkalization in Chinese primary gout patients with benzbromarone: a prospective, randomized controlled study. Rheumatology (Oxford, England). 2021 06; 60(6):2661-2671. doi: 10.1093/rheumatology/keaa668. [PMID: 33211886]
  • Junichiro Uda, Seiichi Kobashi, Naoki Ashizawa, Koji Matsumoto, Takashi Iwanaga. Novel monocyclic amide-linked phenol derivatives without mitochondrial toxicity have potent uric acid-lowering activity. Bioorganic & medicinal chemistry letters. 2021 05; 40(?):127900. doi: 10.1016/j.bmcl.2021.127900. [PMID: 33684442]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Hebatallah M Essam, Heba M Mohamed. Developing, optimizing, and assessing a green electrophoretic method for determination of benzbromarone and allopurinol with its active metabolite in biological and pharmaceutical matrices. Journal of separation science. 2021 Apr; 44(7):1461-1470. doi: 10.1002/jssc.202000934. [PMID: 33527723]
  • Keishi Yamasaki, Akito Kawai, Keiki Sakurama, Nagiko Udo, Yuta Yoshino, Yuki Saito, Kenji Tsukigawa, Koji Nishi, Masaki Otagiri. Interaction of Benzbromarone with Subdomains IIIA and IB/IIA on Human Serum Albumin as the Primary and Secondary Binding Regions. Molecular pharmaceutics. 2021 03; 18(3):1061-1070. doi: 10.1021/acs.molpharmaceut.0c01004. [PMID: 33478218]
  • Jun Xia Zhang, Xue Lin, Jinxiu Xu, Feng Tang. Hyperuricemia Inhibition Protects SD Rats Against Fructose-Induced Obesity Hypertension Via Modulation of Inflammation and Renin-Angiotensin System in Adipose Tissue. Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association. 2021 Mar; 129(4):314-321. doi: 10.1055/a-1023-6710. [PMID: 31683330]
  • Dingyu Wang, Li Sun, Guowei Zhang, Yang Liu, Zhaoguang Liang, Jing Zhao, Shuangli Yin, Mengqi Su, Song Zhang, Ying Wei, He Liu, Desen Liang, Yue Li. Increased Susceptibility of Atrial Fibrillation Induced by Hyperuricemia in Rats: Mechanisms and Implications. Cardiovascular toxicology. 2021 03; 21(3):192-205. doi: 10.1007/s12012-020-09611-4. [PMID: 33099748]
  • Narjes Saheb Sharif-Askari, Fatemeh Saheb Sharif-Askari, Bushra Mdkhana, Saba Al Heialy, Elaref Ratemi, Malak Alghamdi, Salah Abusnana, Tarek Kashour, Qutayba Hamid, Rabih Halwani. Effect of common medications on the expression of SARS-CoV-2 entry receptors in liver tissue. Archives of toxicology. 2020 12; 94(12):4037-4041. doi: 10.1007/s00204-020-02869-1. [PMID: 32808185]
  • Tong Zhao, Qing Meng, Zhuosen Sun, Yanyu Chen, Wei Ai, Zean Zhao, Dongwei Kang, Yue Dong, Ruipeng Liang, Ting Wu, Jianxin Pang, Xinyong Liu, Peng Zhan. Novel Human Urate Transporter 1 Inhibitors as Hypouricemic Drug Candidates with Favorable Druggability. Journal of medicinal chemistry. 2020 10; 63(19):10829-10854. doi: 10.1021/acs.jmedchem.0c00223. [PMID: 32897699]
  • Ines Cabrita, Andre Kraus, Julia Katharina Scholz, Kathrin Skoczynski, Rainer Schreiber, Karl Kunzelmann, Björn Buchholz. Cyst growth in ADPKD is prevented by pharmacological and genetic inhibition of TMEM16A in vivo. Nature communications. 2020 08; 11(1):4320. doi: 10.1038/s41467-020-18104-5. [PMID: 32859916]
  • Luisa Möhle, Barbora Schwarzová, Markus Krohn, Sven Marcel Stefan, Jens Pahnke. Using a qPCR device to screen for modulators of ABC transporter activity: A step-by-step protocol. Journal of pharmacological and toxicological methods. 2020 Jul; 104(?):106882. doi: 10.1016/j.vascn.2020.106882. [PMID: 32474136]
  • Christopher L Gardner, Danilo R da Silva, Fernando A Pagliai, Lei Pan, Kaylie A Padgett-Pagliai, Ryan A Blaustein, Marcelo L Merli, Dan Zhang, Cécile Pereira, Max Teplitski, Jose X Chaparro, Svetlana Y Folimonova, Ana Conesa, Salvador Gezan, Graciela L Lorca, Claudio F Gonzalez. Assessment of unconventional antimicrobial compounds for the control of 'Candidatus Liberibacter asiaticus', the causative agent of citrus greening disease. Scientific reports. 2020 03; 10(1):5395. doi: 10.1038/s41598-020-62246-x. [PMID: 32214166]
  • Tatsuo Hosoya, Takafumi Sano, Tomomitsu Sasaki, Masahiko Fushimi, Tetsuo Ohashi. Dotinurad versus benzbromarone in Japanese hyperuricemic patient with or without gout: a randomized, double-blind, parallel-group, phase 3 study. Clinical and experimental nephrology. 2020 Mar; 24(Suppl 1):62-70. doi: 10.1007/s10157-020-01849-0. [PMID: 31980978]
  • Yoshitaka Kimura, Tamiko Yanagida, Akiko Onda, Daisuke Tsukui, Makoto Hosoyamada, Hajime Kono. Soluble Uric Acid Promotes Atherosclerosis via AMPK (AMP-Activated Protein Kinase)-Mediated Inflammation. Arteriosclerosis, thrombosis, and vascular biology. 2020 03; 40(3):570-582. doi: 10.1161/atvbaha.119.313224. [PMID: 31996020]
  • Satoru Kuriyama. Dotinurad: a novel selective urate reabsorption inhibitor as a future therapeutic option for hyperuricemia. Clinical and experimental nephrology. 2020 Mar; 24(Suppl 1):1-5. doi: 10.1007/s10157-019-01811-9. [PMID: 31754883]
  • Esraa Abdel-Nassir Abdel-Razek, Amira M Abo-Youssef, Amany A Azouz. Benzbromarone mitigates cisplatin nephrotoxicity involving enhanced peroxisome proliferator-activated receptor-alpha (PPAR-α) expression. Life sciences. 2020 Feb; 243(?):117272. doi: 10.1016/j.lfs.2020.117272. [PMID: 31926251]
  • Hanna Ellmann, Sara Bayat, Elizabeth Araujo, Bernhard Manger, Arnd Kleyer, Alexander Cavallaro, Michael Lell, Hannah Schenker, David Simon, Koray Tascilar, Herbert S B Baraf, Georg Schett, Jürgen Rech. Effects of Conventional Uric Acid-Lowering Therapy on Monosodium Urate Crystal Deposits. Arthritis & rheumatology (Hoboken, N.J.). 2020 01; 72(1):150-156. doi: 10.1002/art.41063. [PMID: 31353871]
  • Leonardo Santos Hoff, Claudia Goldenstein-Schainberg, Ricardo Fuller. Nephrolithiasis in gout: prevalence and characteristics of Brazilian patients. Advances in rheumatology (London, England). 2019 12; 60(1):2. doi: 10.1186/s42358-019-0106-4. [PMID: 31892344]
  • Xuechen Li, Zhenxin Yan, Jinying Tian, Xiaolin Zhang, Huirong Han, Fei Ye. Urate Transporter URAT1 in Hyperuricemia: New Insights from Hyperuricemic Models. Annals of clinical and laboratory science. 2019 Nov; 49(6):756-762. doi: NULL. [PMID: 31882426]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Ting-Ting Chung, Kuang-Hui Yu, Chang-Fu Kuo, Shue-Fen Luo, Meng-Jiun Chiou, Wen-Ching Lan, Jung-Sheng Chen, Wen-Yi Tseng, Ao-Ho Hsieh, Lian-Chin Wang. Impact of urate-lowering drugs on the progression and recovery from chronic kidney disease among gout patients. Arthritis research & therapy. 2019 09; 21(1):210. doi: 10.1186/s13075-019-1993-9. [PMID: 31533805]
  • Nan Liang, Mingshu Sun, Ruixia Sun, Ting Xu, Lingling Cui, Can Wang, Lidan Ma, Xiaoyu Cheng, Xiaomei Xue, Wenyan Sun, Xuan Yuan, Hui Zhang, Hailong Li, Yuwei He, Aichang Ji, Xinjiang Wu, Changgui Li. Baseline urate level and renal function predict outcomes of urate-lowering therapy using low doses of febuxostat and benzbromarone: a prospective, randomized controlled study in a Chinese primary gout cohort. Arthritis research & therapy. 2019 09; 21(1):200. doi: 10.1186/s13075-019-1976-x. [PMID: 31477161]
  • Valderilio Feijó Azevedo, Igor Age Kos, Ana Beatriz Vargas-Santos, Geraldo da Rocha Castelar Pinheiro, Eduardo Dos Santos Paiva. Benzbromarone in the treatment of gout. Advances in rheumatology (London, England). 2019 08; 59(1):37. doi: 10.1186/s42358-019-0080-x. [PMID: 31391099]
  • Jing Wu, Yu-Ping Zhang, Yuan Qu, Li-Gang Jie, Jia-Xin Deng, Qing-Hong Yu. Efficacy of uric acid-lowering therapy on hypercholesterolemia and hypertriglyceridemia in gouty patients. International journal of rheumatic diseases. 2019 Aug; 22(8):1445-1451. doi: 10.1111/1756-185x.13652. [PMID: 31317680]
  • Akinori Takemura, Simin Gong, Shuichi Sekine, Kousei Ito. Inhibition of biliary network reconstruction by benzbromarone delays recovery from pre-existing liver injury. Toxicology. 2019 07; 423(?):32-41. doi: 10.1016/j.tox.2019.05.004. [PMID: 31102694]
  • Menaka C Thounaojam, Annalisa Montemari, Folami L Powell, Prerana Malla, Diana R Gutsaeva, Alessandra Bachettoni, Guido Ripandelli, Andrea Repossi, Amany Tawfik, Pamela M Martin, Francesco Facchiano, Manuela Bartoli. Monosodium Urate Contributes to Retinal Inflammation and Progression of Diabetic Retinopathy. Diabetes. 2019 05; 68(5):1014-1025. doi: 10.2337/db18-0912. [PMID: 30728185]
  • Xiaolan Ye, Jian Wu, Kun Tang, Wenge Li, Cunquan Xiong, Li Zhuo. Benzbromarone as a possible cause of acute kidney injury in patients with urolithiasis: Two case reports. Medicine. 2019 Apr; 98(15):e15214. doi: 10.1097/md.0000000000015214. [PMID: 30985721]
  • Xinrui Li, Jing Liu, Liang Ma, Ping Fu. Pharmacological urate-lowering approaches in chronic kidney disease. European journal of medicinal chemistry. 2019 Mar; 166(?):186-196. doi: 10.1016/j.ejmech.2019.01.043. [PMID: 30769179]
  • Haibo Yu, Xinying Liu, Yaxiang Song, Jiafen Cheng, Hui Bao, Ling Qin, Xuan Zhou, Ling Wang, Ai Peng. Safety and Efficacy of Benzbromarone and Febuxostat in Hyperuricemia Patients with Chronic Kidney Disease: A Prospective Pilot Study. Clinical and experimental nephrology. 2018 Dec; 22(6):1324-1330. doi: 10.1007/s10157-018-1586-y. [PMID: 29761242]
  • Geofrey Sing'ombe Ombiro, Taku Sawai, Yoshiteru Noutoshi, Yuta Nishina, Hidenori Matsui, Mikihiro Yamamoto, Kazuhiro Toyoda, Yuki Ichinose. Specific growth inhibitors of Ralstonia solanacearum, Xanthomonas oryzae pv. oryzae, X. campestris pv. campestris, and Clavibacter michiganensis subsp. michiganensis. Microbiological research. 2018 Oct; 215(?):29-35. doi: 10.1016/j.micres.2018.06.005. [PMID: 30172306]
  • Hsu-Wen Chou, Hsien-Tsai Chiu, Ching-Wei Tsai, I-Wen Ting, Hung-Chieh Yeh, Han-Chun Huang, Chin-Chi Kuo. Comparative effectiveness of allopurinol, febuxostat and benzbromarone on renal function in chronic kidney disease patients with hyperuricemia: a 13-year inception cohort study. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2018 09; 33(9):1620-1627. doi: 10.1093/ndt/gfx313. [PMID: 29165620]
  • Masanari Shiramoto, Sha Liu, Zancong Shen, Xiaohong Yan, Amy Yamamoto, Michael Gillen, Yasushi Ito, Jesse Hall. Verinurad combined with febuxostat in Japanese adults with gout or asymptomatic hyperuricaemia: a phase 2a, open-label study. Rheumatology (Oxford, England). 2018 09; 57(9):1602-1610. doi: 10.1093/rheumatology/key100. [PMID: 29868853]
  • Peng Sun, Jing-Jie Zhu, Ting Wang, Qi Huang, Yu-Ren Zhou, Bang-Wei Yu, Hua-Liang Jiang, He-Yao Wang. Benzbromarone aggravates hepatic steatosis in obese individuals. Biochimica et biophysica acta. Molecular basis of disease. 2018 06; 1864(6 Pt A):2067-2077. doi: 10.1016/j.bbadis.2018.03.009. [PMID: 29526820]
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  • Hui Wang, Ying Peng, Tingjian Zhang, Qunsheng Lan, Huimin Zhao, Wenbao Wang, Yufei Zhao, Xu Wang, Jianxin Pang, Shaojie Wang, Jiang Zheng. Metabolic Epoxidation Is a Critical Step for the Development of Benzbromarone-Induced Hepatotoxicity. Drug metabolism and disposition: the biological fate of chemicals. 2017 12; 45(12):1354-1363. doi: 10.1124/dmd.117.077818. [PMID: 29021351]
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