Ticrynafen (BioDeep_00000008814)

 

Secondary id: BioDeep_00001871379

human metabolite blood metabolite


代谢物信息卡片


2-[2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy]acetic acid

化学式: C13H8Cl2O4S (329.95203480000004)
中文名称: 替宁酸
谱图信息: 最多检出来源 Homo sapiens(blood) 97.62%

分子结构信息

SMILES: C1=CSC(=C1)C(=O)C2=C(C(=C(C=C2)OCC(=O)O)Cl)Cl
InChI: InChI=1S/C13H8Cl2O4S/c14-11-7(13(18)9-2-1-5-20-9)3-4-8(12(11)15)19-6-10(16)17/h1-5H,6H2,(H,16,17)

描述信息

C - Cardiovascular system > C03 - Diuretics > C03C - High-ceiling diuretics > C03CC - Aryloxyacetic acid derivatives
D018501 - Antirheumatic Agents > D006074 - Gout Suppressants > D014528 - Uricosuric Agents
C78275 - Agent Affecting Blood or Body Fluid > C448 - Diuretic > C49184 - Loop Diuretic
D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents
D002317 - Cardiovascular Agents > D045283 - Natriuretic Agents
C26170 - Protective Agent > C921 - Uricosuric Agent
D045283 - Natriuretic Agents > D004232 - Diuretics
Same as: D02386

同义名列表

19 个代谢物同义名

2-[2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy]acetic acid; (2,3-Dichloro-4-(2-thiophenecarbonyl)phenoxy)acetic acid; (2,3-Dichloro-4-(2-thiophenecarbonyl)phenoxy)acetate; 4-(2-Thienylketo)-2,3-dichlorophenoxyacetic acid; (2,3-Dichloro-4-(2-thenoyl)phenoxy)acetic acid; 4-(2-Thienylketo)-2,3-dichlorophenoxyacetate; 4-(2-Theonyl)-2,3-dichlorphenoxyessigsaeure; (2,3-Dichloro-4-(2-thenoyl)phenoxy)acetate; Acidum tienilicum; Acide tienilique; Acido tienilico; Acid, thienylic; Acid, tienilic; Thienylic acid; Tienilic acid; Ticrynafen; Thienylate; Tienilate; Selacryn



数据库引用编号

15 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

  • Tomonori Miura, Shotaro Uehara, Makiko Shimizu, Norie Murayama, Masahiro Utoh, Hiroshi Suemizu, Hiroshi Yamazaki. Different Roles of Human Cytochrome P450 2C9 and 3A Enzymes in Diclofenac 4'- and 5-Hydroxylations Mediated by Metabolically Inactivated Human Hepatocytes in Previously Transplanted Chimeric Mice. Chemical research in toxicology. 2020 02; 33(2):634-639. doi: 10.1021/acs.chemrestox.9b00446. [PMID: 31854189]
  • 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]
  • Adam M King, Isobelle Grant, Paul D Rainville, Giorgis Isaac, Muireann Coen, Ian D Wilson, Robert S Plumb. Capillary ultra performance liquid chromatography-tandem mass spectrometry analysis of tienilic acid metabolites in urine following intravenous administration to the rat. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2018 Jun; 1087-1088(?):142-148. doi: 10.1016/j.jchromb.2018.04.034. [PMID: 29738964]
  • Muireann Coen, Peter M Rademacher, Wei Zou, Michael Scott, Patricia E Ganey, Robert Roth, Sidney D Nelson. Comparative NMR-based metabonomic investigation of the metabolic phenotype associated with tienilic acid and tienilic acid isomer. Chemical research in toxicology. 2012 Nov; 25(11):2412-22. doi: 10.1021/tx3002803. [PMID: 23013248]
  • Takayoshi Nishiya, Michiyuki Kato, Takami Suzuki, Chikako Maru, Hiroko Kataoka, Chiharu Hattori, Kazuhiko Mori, Toshimasa Jindo, Yorihisa Tanaka, Sunao Manabe. Involvement of cytochrome P450-mediated metabolism in tienilic acid hepatotoxicity in rats. Toxicology letters. 2008 Dec; 183(1-3):81-9. doi: 10.1016/j.toxlet.2008.10.009. [PMID: 18992796]
  • Takayoshi Nishiya, Kazuhiko Mori, Chiharu Hattori, Kiyonori Kai, Hiroko Kataoka, Noriko Masubuchi, Toshimasa Jindo, Sunao Manabe. The crucial protective role of glutathione against tienilic acid hepatotoxicity in rats. Toxicology and applied pharmacology. 2008 Oct; 232(2):280-91. doi: 10.1016/j.taap.2008.06.024. [PMID: 18708081]
  • Yasuhiro Masubuchi, Toshiharu Horie. Toxicological significance of mechanism-based inactivation of cytochrome p450 enzymes by drugs. Critical reviews in toxicology. 2007 Jun; 37(5):389-412. doi: 10.1080/10408440701215233. [PMID: 17612953]
  • Noriko Masubuchi, Chie Makino, Nobuyuki Murayama. Prediction of in vivo potential for metabolic activation of drugs into chemically reactive intermediate: correlation of in vitro and in vivo generation of reactive intermediates and in vitro glutathione conjugate formation in rats and humans. Chemical research in toxicology. 2007 Mar; 20(3):455-64. doi: 10.1021/tx060234h. [PMID: 17309281]
  • Takayoshi Nishiya, Hiroko Kataoka, Kazuhiko Mori, Mayumi Goto, Tadaki Sugawara, Kazuhisa Furuhama. Tienilic acid enhances hyperbilirubinemia in Eisai hyperbilirubinuria rats through hepatic multidrug resistance-associated protein 3 and heme oxygenase-1 induction. Toxicological sciences : an official journal of the Society of Toxicology. 2006 Jun; 91(2):651-9. doi: 10.1093/toxsci/kfj162. [PMID: 16543292]
  • Jochen Beyer, Anabelle Bierl, Frank T Peters, Hans H Maurer. Screening procedure for detection of diuretics and uricosurics and/or their metabolites in human urine using gas chromatography-mass spectrometry after extractive methylation. Therapeutic drug monitoring. 2005 Aug; 27(4):509-20. doi: 10.1097/01.ftd.0000160719.96445.91. [PMID: 16044110]
  • J-P Villeneuve, V Pichette. Cytochrome P450 and liver diseases. Current drug metabolism. 2004 Jun; 5(3):273-82. doi: 10.2174/1389200043335531. [PMID: 15180496]
  • E Bonierbale, P Valadon, C Pons, B Desfosses, P M Dansette, D Mansuy. Opposite behaviors of reactive metabolites of tienilic acid and its isomer toward liver proteins: use of specific anti-tienilic acid-protein adduct antibodies and the possible relationship with different hepatotoxic effects of the two compounds. Chemical research in toxicology. 1999 Mar; 12(3):286-96. doi: 10.1021/tx980136z. [PMID: 10077492]
  • P M Dansette, E Bonierbale, C Minoletti, P H Beaune, D Pessayre, D Mansuy. Drug-induced immunotoxicity. European journal of drug metabolism and pharmacokinetics. 1998 Oct; 23(4):443-51. doi: 10.1007/bf03189993. [PMID: 10323325]
  • F Roch-Ramel, B Guisan, J Diezi. Effects of uricosuric and antiuricosuric agents on urate transport in human brush-border membrane vesicles. The Journal of pharmacology and experimental therapeutics. 1997 Feb; 280(2):839-45. doi: . [PMID: 9023298]
  • P H Beaune, S Lecoeur. Immunotoxicology of the liver: adverse reactions to drugs. Journal of hepatology. 1997; 26 Suppl 2(?):37-42. doi: 10.1016/s0168-8278(97)80495-3. [PMID: 9204408]
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  • M A Robin, M Maratrat, M Le Roy, F P Le Breton, E Bonierbale, P Dansette, F Ballet, D Mansuy, D Pessayre. Antigenic targets in tienilic acid hepatitis. Both cytochrome P450 2C11 and 2C11-tienilic acid adducts are transported to the plasma membrane of rat hepatocytes and recognized by human sera. The Journal of clinical investigation. 1996 Sep; 98(6):1471-80. doi: 10.1172/jci118936. [PMID: 8823314]
  • S Lecoeur, C André, P H Beaune. Tienilic acid-induced autoimmune hepatitis: anti-liver and-kidney microsomal type 2 autoantibodies recognize a three-site conformational epitope on cytochrome P4502C9. Molecular pharmacology. 1996 Aug; 50(2):326-33. doi: . [PMID: 8700140]
  • P H Beaune, S Lecoeur, M Bourdi, A Gauffre, C Belloc, P Dansette, D Mansuy. Anti-cytochrome P450 autoantibodies in drug-induced disease. European journal of haematology. Supplementum. 1996; 60(?):89-92. doi: 10.1111/j.1600-0609.1996.tb01652.x. [PMID: 8987248]
  • S Lecoeur, E Bonierbale, D Challine, J C Gautier, P Valadon, P M Dansette, R Catinot, F Ballet, D Mansuy, P H Beaune. Specificity of in vitro covalent binding of tienilic acid metabolites to human liver microsomes in relationship to the type of hepatotoxicity: comparison with two directly hepatotoxic drugs. Chemical research in toxicology. 1994 May; 7(3):434-42. doi: 10.1021/tx00039a023. [PMID: 8075377]
  • M P Lopez Garcia, P M Dansette, P Valadon, C Amar, P H Beaune, F P Guengerich, D Mansuy. Human-liver cytochromes P-450 expressed in yeast as tools for reactive-metabolite formation studies. Oxidative activation of tienilic acid by cytochromes P-450 2C9 and 2C10. European journal of biochemistry. 1993 Apr; 213(1):223-32. doi: 10.1111/j.1432-1033.1993.tb17752.x. [PMID: 8477697]
  • C Pons, P M Dansette, C Amar, M Jaouen, C R Wolf, J Gregeois, J C Homberg, D Mansuy. Detection of human hepatitis anti-liver kidney microsomes (LKM2) autoantibodies on rat liver sections is predominantly due to reactivity with rat liver P-450 IIC11. The Journal of pharmacology and experimental therapeutics. 1991 Dec; 259(3):1328-34. doi: NULL. [PMID: 1762080]
  • T Dan, E Onuma, H Tanaka, H Koga. A selective uricosuric action of AA-193 in rats. Comparison with its effect on PAH secretion in vivo and in vitro. Naunyn-Schmiedeberg's archives of pharmacology. 1991 May; 343(5):532-7. doi: 10.1007/bf00169557. [PMID: 1881462]
  • S Takagi, S Takayama, T Onodera. Hepatotoxicity of DR-3438, tienilic acid, indacrinone and furosemide studied in vitro. Toxicology letters. 1991 Mar; 55(3):287-93. doi: 10.1016/0378-4274(91)90009-u. [PMID: 2003271]
  • T Shinosaki, Y Yonetani. Stop-flow studies on tubular transport of uric acid in rats. Advances in experimental medicine and biology. 1989; 253A(?):293-300. doi: 10.1007/978-1-4684-5673-8_49. [PMID: 2624206]
  • P Ayotte, D Pilon, G L Plaa. Failure of phenobarbital or butanediol pretreatment to potentiate tienilic acid hepatotoxicity in vivo in the rat. Archives internationales de pharmacodynamie et de therapie. 1987 Mar; 286(1):49-57. doi: . [PMID: 3592860]
  • P Beaune, P M Dansette, D Mansuy, L Kiffel, M Finck, C Amar, J P Leroux, J C Homberg. Human anti-endoplasmic reticulum autoantibodies appearing in a drug-induced hepatitis are directed against a human liver cytochrome P-450 that hydroxylates the drug. Proceedings of the National Academy of Sciences of the United States of America. 1987 Jan; 84(2):551-5. doi: 10.1073/pnas.84.2.551. [PMID: 3540968]
  • J C Homberg, N Abuaf, S Helmy-Khalil, M Biour, R Poupon, S Islam, F Darnis, V G Levy, P Opolon, M Beaugrand. Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies. Hepatology (Baltimore, Md.). 1985 Sep; 5(5):722-7. doi: 10.1002/hep.1840050504. [PMID: 4029887]
  • A Lant. Diuretics. Clinical pharmacology and therapeutic use (Part II). Drugs. 1985 Feb; 29(2):162-88. doi: 10.2165/00003495-198529020-00003. [PMID: 3884320]
  • J C Homberg. [Autoimmunity induced by drugs. Immunological characteristics and etiopathogenic hypotheses]. Presse medicale (Paris, France : 1983). 1984 Dec; 13(45):2755-60. doi: . [PMID: 6240048]
  • J Mironneau, J P Savineau, C Mironneau. Effect of tienilic acid on the electromechanical properties of vascular smooth muscles in normotensive and spontaneously hypertensive rats. Journal of cardiovascular pharmacology. 1984 Nov; 6(6):1177-83. doi: 10.1097/00005344-198411000-00027. [PMID: 6084777]
  • J J Plattner, A K Fung, J A Parks, R J Pariza, S R Crowley, A G Pernet, P R Bunnell, P W Dodge. Substituted 5,6-dihydrofuro[3,2-f]-1,2-benzisoxazole-6-carboxylic acids: high-ceiling diuretics with uricosuric activity. Journal of medicinal chemistry. 1984 Aug; 27(8):1016-26. doi: 10.1021/jm00374a014. [PMID: 6431103]
  • D Mansuy, P M Dansette, C Foures, M Jaouen, G Moinet, N Bayer. Metabolic hydroxylation of the thiophene ring: isolation of 5-hydroxy-tienilic acid as the major urinary metabolite of tienilic acid in man and rat. Biochemical pharmacology. 1984 May; 33(9):1429-35. doi: 10.1016/0006-2952(84)90409-x. [PMID: 6732860]
  • J C Homberg, C Andre, N Abuaf. A new anti-liver-kidney microsome antibody (anti-LKM2) in tienilic acid-induced hepatitis. Clinical and experimental immunology. 1984 Mar; 55(3):561-70. doi: . [PMID: 6368059]
  • H J Zimmerman, J H Lewis, K G Ishak, W C Maddrey. Ticrynafen-associated hepatic injury: analysis of 340 cases. Hepatology (Baltimore, Md.). 1984 Mar; 4(2):315-23. doi: 10.1002/hep.1840040223. [PMID: 6706306]
  • D A Koechel, G C Budd, N S Bretz. Acute effects of alkylating agents on canine renal function and ultrastructure: high-dose ethacrynic acid vs. dihydroethacrynic acid and ticrynafen. The Journal of pharmacology and experimental therapeutics. 1984 Mar; 228(3):799-809. doi: . [PMID: 6707927]
  • R Sellman, M G Parkki. Induction of microsomal epoxide hydrolase by tienilic acid in the rat. Journal of applied toxicology : JAT. 1983 Oct; 3(5):245-8. doi: 10.1002/jat.2550030505. [PMID: 6662998]
  • P C Preusch, J W Suttie. Mechanism of ticrynafen potentiation of coumarin anticoagulant action. Biochemical pharmacology. 1983 Aug; 32(16):2393-8. doi: 10.1016/0006-2952(83)90681-0. [PMID: 6615542]
  • . Multicentre controlled trial of tienilic acid in hyperuricaemic, hypertensive subjects, with intensive monitoring of liver function. British journal of clinical pharmacology. 1983 May; 15(5):513-8. doi: 10.1111/j.1365-2125.1983.tb02084.x. [PMID: 6344896]
  • J P Lafay, R Poupon, C Legendre, J C Homberg, F Darnis. [Hepatic lesions associated with antimicrosomal antibodies of the liver and kidney (type 2) and the taking of tienilic acid. A study of 37 cases]. Gastroenterologie clinique et biologique. 1983 May; 7(5):523-8. doi: NULL. [PMID: 6873565]
  • L A Ferrara, A Siani, P Strazzullo, F Galletti. Long term treatment with tienilic acid or thiazides: comparison of antihypertensive and metabolic effects. European journal of clinical pharmacology. 1983; 25(6):835-7. doi: 10.1007/bf00542531. [PMID: 6662184]
  • P Weidmann, A Meier, R Mordasini, W Riesenachmann, E Peheim. [Diuretic treatment and serum lipoproteins: effects of tienilic acid and indapamide (author's transl)]. Schweizerische Rundschau fur Medizin Praxis = Revue suisse de medecine Praxis. 1982 Feb; 71(7):289-92. doi: NULL. [PMID: 7111214]
  • W Stüber, E Mutschler, D Steinbach. Determination of ethacrynic and tienilic acid in plasma by gas--liquid chromatography--mass spectrometry. Journal of chromatography. 1982 Jan; 227(1):193-8. doi: 10.1016/s0378-4347(00)80371-0. [PMID: 7056811]
  • A Eisalo, K J Tötterman, E Haapanen. Tienilic acid in patients with impaired renal function. Acta medica Scandinavica. Supplementum. 1982; 668(?):110-3. doi: 10.1111/j.0954-6820.1982.tb08531.x. [PMID: 6762807]
  • B T Emmerson, P J Renshaw, P J Ravenscroft, I Denham, S Schey. Ticrynafen and hydrochlorothiazide. A comparison in hypertensive patients with renal impairment. European journal of clinical pharmacology. 1982; 22(3):203-6. doi: 10.1007/bf00545215. [PMID: 7049708]
  • A Salvetti, R Pedrinelli, P Sassano, F Arzilli, F Turini. Effects of prostaglandins inhibition on changes in active and inactive renin induced by antihypertensive drugs. Clinical and experimental hypertension. Part A, Theory and practice. 1982; 4(11-12):2435-48. doi: 10.3109/10641968209062401. [PMID: 6756707]
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  • H Danĕková, A Krechnáková, R Dzúrik, V Fedelesová. [Tienilic acid in the treatment of hyperuricemia syndrome (author's transl)]. Bratislavske lekarske listy. 1981 Dec; 76(6):673-82. doi: NULL. [PMID: 7317803]
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  • E Ambrosioni, F Tartagni, A M Lusa, L Bassein, B Magnani. Effects of tienilic acid used alone and in association with triamterene or amiloride on urinary excretion of electrolytes. International journal of clinical pharmacology, therapy, and toxicology. 1981 Oct; 19(10):445-9. doi: NULL. [PMID: 7287241]
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  • P Weidmann, A Meier, R Mordasini, W Riesen, C Bachmann, E Peheim. Diuretic treatment and serum lipoproteins: effects of tienilic acid and indapamide. Klinische Wochenschrift. 1981 Apr; 59(7):343-6. doi: 10.1007/bf01525002. [PMID: 7241956]
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