(+/-)-4-Hydroxy Mephenytoin (BioDeep_00001875902)

Main id: BioDeep_00000033139

 

PANOMIX_OTCML-2023


代谢物信息卡片


5-ethyl-5-(4-hydroxyphenyl)-3-methylimidazolidine-2,4-dione

化学式: C12H14N2O3 (234.1004374)
中文名称: 羟基香豆素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CCC1(C(=O)N(C(=O)N1)C)C2=CC=C(C=C2)O
InChI: InChI=1S/C12H14N2O3/c1-3-12(8-4-6-9(15)7-5-8)10(16)14(2)11(17)13-12/h4-7,15H,3H2,1-2H3,(H,13,17)

描述信息

4-Hydroxymephenytoin is a metabolism of an antiepileptic agent mephenytoin, which is used as a CYP2C19 substrate.
4-Hydroxymephenytoin is a metabolism of an antiepileptic agent mephenytoin, which is used as a CYP2C19 substrate.

同义名列表

3 个代谢物同义名

5-ethyl-5-(4-hydroxyphenyl)-3-methylimidazolidine-2,4-dione; (+/-)-4-Hydroxy Mephenytoin; 4-Hydroxymephenytoin



数据库引用编号

5 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)

0 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

  • Reginald F Frye, Nathalie K Zgheib, Gary R Matzke, Diego Chaves-Gnecco, Mordechai Rabinovitz, Obaid S Shaikh, Robert A Branch. Liver disease selectively modulates cytochrome P450--mediated metabolism. Clinical pharmacology and therapeutics. 2006 Sep; 80(3):235-45. doi: 10.1016/j.clpt.2006.05.006. [PMID: 16952490]
  • Britt Jansson, Doaa Elsherbiny, Ulrika S H Simonsson. Enantiospecific separation and quantitation of mephenytoin and its metabolites nirvanol and 4'-hydroxymephenytoin in human plasma and urine by liquid chromatography/tandem mass spectrometry. Rapid communications in mass spectrometry : RCM. 2006; 20(3):463-72. doi: 10.1002/rcm.2324. [PMID: 16395737]
  • Lian-Sheng Wang, Bing Zhu, A M Abd El-Aty, Gan Zhou, Zhi Li, Jun Wu, Guo-Lin Chen, Jie Liu, Zhi Rong Tang, Wang An, Qing Li, Dan Wang, Hong-Hao Zhou. The influence of St John's Wort on CYP2C19 activity with respect to genotype. Journal of clinical pharmacology. 2004 Jun; 44(6):577-81. doi: 10.1177/0091270004265642. [PMID: 15145964]
  • Tobias Klaassen, Dirk Kasel, Stefanie Harlfinger, Uwe Fuhr. Quantification of mephenytoin and its metabolites 4'-hydroxymephenytoin and nirvanol in human urine using a simple sample processing method. Rapid communications in mass spectrometry : RCM. 2004; 18(15):1675-80. doi: 10.1002/rcm.1539. [PMID: 15282764]
  • Britt Jansson, Ulrika S H Simonsson, Michael Ashton. Simultaneous enantiospecific separation and quantitation of mephenytoin and its metabolites nirvanol and 4'-hydroxymephenytoin in human plasma by liquid chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2003 Jul; 791(1-2):179-91. doi: 10.1016/s1570-0232(03)00221-6. [PMID: 12798178]
  • Caiping Yao, Kent L Kunze, William F Trager, Evan D Kharasch, René H Levy. Comparison of in vitro and in vivo inhibition potencies of fluvoxamine toward CYP2C19. Drug metabolism and disposition: the biological fate of chemicals. 2003 May; 31(5):565-71. doi: 10.1124/dmd.31.5.565. [PMID: 12695344]
  • Xiao-Ping Chen, Zhi-Rong Tan, Song-Lin Huang, Zheng Huang, Dong-Sheng Ou-Yang, Hong-Hao Zhou. Isozyme-specific induction of low-dose aspirin on cytochrome P450 in healthy subjects. Clinical pharmacology and therapeutics. 2003 Mar; 73(3):264-71. doi: 10.1067/mcp.2003.14. [PMID: 12621391]
  • Reginald F Frye, Virginia M Schneider, Carole S Frye, Arthur M Feldman. Plasma levels of TNF-alpha and IL-6 are inversely related to cytochrome P450-dependent drug metabolism in patients with congestive heart failure. Journal of cardiac failure. 2002 Oct; 8(5):315-9. doi: 10.1054/jcaf.2002.127773. [PMID: 12411982]
  • A Adedoyin, P A Arns, W O Richards, G R Wilkinson, R A Branch. Selective effect of liver disease on the activities of specific metabolizing enzymes: investigation of cytochromes P450 2C19 and 2D6. Clinical pharmacology and therapeutics. 1998 Jul; 64(1):8-17. doi: 10.1016/s0009-9236(98)90017-0. [PMID: 9695714]
  • H J Feng, S L Huang, W Wang, H H Zhou. The induction effect of rifampicin on activity of mephenytoin 4'-hydroxylase related to M1 mutation of CYP2C19 and gene dose. British journal of clinical pharmacology. 1998 Jan; 45(1):27-9. doi: 10.1046/j.1365-2125.1998.00643.x. [PMID: 9489590]
  • M Tanaka, T Ohkubo, K Otani, A Suzuki, S Kaneko, K Sugawara, Y Ryokawa, H Hakusui, S Yamamori, T Ishizaki. Metabolic disposition of pantoprazole, a proton pump inhibitor, in relation to S-mephenytoin 4'-hydroxylation phenotype and genotype. Clinical pharmacology and therapeutics. 1997 Dec; 62(6):619-28. doi: 10.1016/s0009-9236(97)90081-3. [PMID: 9433390]
  • H G Xie, Z H Xu, S L Huang, J H Liu, J X Wu, C H Jiang, H H Zhou. No correlation between side-chain of propranolol oxidation and S-mephenytoin 4'-hydroxylase activity. Zhongguo yao li xue bao = Acta pharmacologica Sinica. 1997 May; 18(3):216-8. doi: NULL. [PMID: 10072936]
  • M Tanaka, K Kato, K Sudo, H Hakusui, T Ohkubo, K Sugawara, S Kaneko, K Otani, K Chiba, T Ishizaki. Simple and selective assay of 4-hydroxymephenytoin in human urine using solid-phase extraction and high-performance liquid chromatography with electrochemical detection and its preliminary application to phenotyping test. Journal of chromatography. B, Biomedical applications. 1996 Feb; 676(1):87-94. doi: 10.1016/0378-4347(95)00411-4. [PMID: 8852048]
  • P J Wedlund, G R Wilkinson. In vivo and in vitro measurement of CYP2C19 activity. Methods in enzymology. 1996; 272(?):105-14. doi: 10.1016/s0076-6879(96)72013-x. [PMID: 8791767]
  • H F Hadidi, Y M Irshaid, R L Woosley, J R Idle, D A Flockhart. S-mephenytoin hydroxylation phenotypes in a Jordanian population. Clinical pharmacology and therapeutics. 1995 Nov; 58(5):542-7. doi: 10.1016/0009-9236(95)90174-4. [PMID: 7586948]
  • H G Xie, S L Huang, H H Zhou. High-performance liquid chromatographic determination of urinary 4'-hydroxymephenytoin, a metabolic marker for the hepatic enzyme CYP2C19, in humans. Journal of chromatography. B, Biomedical applications. 1995 Jun; 668(1):125-31. doi: 10.1016/0378-4347(95)00065-q. [PMID: 7550968]
  • J Caslavska, E Hufschmid, R Theurillat, C Desiderio, H Wolfisberg, W Thormann. Screening for hydroxylation and acetylation polymorphisms in man via simultaneous analysis of urinary metabolites of mephenytoin, dextromethorphan and caffeine by capillary electrophoretic procedures. Journal of chromatography. B, Biomedical applications. 1994 Jun; 656(1):219-31. doi: 10.1016/0378-4347(94)00059-x. [PMID: 7952033]
  • C Desiderio, S Fanali, A Küpfer, W Thormann. Analysis of mephenytoin, 4-hydroxymephenytoin and 4-hydroxyphenytoin enantiomers in human urine by cyclodextrin micellar electrokinetic capillary chromatography: simple determination of a hydroxylation polymorphism in man. Electrophoresis. 1994 Jan; 15(1):87-93. doi: 10.1002/elps.1150150113. [PMID: 8143685]
  • Z R Ruan, Y S Cheng, D Y Ding. [Determination of mephenytoin and 4'-hydroxymephenytoin in urine by high performance liquid chromatography]. Yao xue xue bao = Acta pharmaceutica Sinica. 1994; 29(8):624-8. doi: NULL. [PMID: 7985520]
  • D R Sohn, M Kusaka, T Ishizaki, S G Shin, I J Jang, J G Shin, K Chiba. Incidence of S-mephenytoin hydroxylation deficiency in a Korean population and the interphenotypic differences in diazepam pharmacokinetics. Clinical pharmacology and therapeutics. 1992 Aug; 52(2):160-9. doi: 10.1038/clpt.1992.125. [PMID: 1505151]
  • Y Horsmans, D Lannes, D Larrey, M Tinel, P Letteron, J Loeper, D Pessayre. Nilutamide inhibits mephenytoin 4-hydroxylation in untreated male rats and in human liver microsomes. Xenobiotica; the fate of foreign compounds in biological systems. 1991 Dec; 21(12):1559-70. doi: 10.3109/00498259109044405. [PMID: 1785203]
  • H H Zhou, L B Anthony, A J Wood, G R Wilkinson. Induction of polymorphic 4'-hydroxylation of S-mephenytoin by rifampicin. British journal of clinical pharmacology. 1990 Sep; 30(3):471-5. doi: 10.1111/j.1365-2125.1990.tb03799.x. [PMID: 2223426]
  • A Küpfer, R A Branch. Stereoselective mephobarbital hydroxylation cosegregates with mephenytoin hydroxylation. Clinical pharmacology and therapeutics. 1985 Oct; 38(4):414-8. doi: 10.1038/clpt.1985.196. [PMID: 4042524]
  • P J Wedlund, W S Aslanian, C B McAllister, G R Wilkinson, R A Branch. Mephenytoin hydroxylation deficiency in Caucasians: frequency of a new oxidative drug metabolism polymorphism. Clinical pharmacology and therapeutics. 1984 Dec; 36(6):773-80. doi: 10.1038/clpt.1984.256. [PMID: 6499356]
  • A Küpfer, R Patwardhan, S Ward, S Schenker, R Preisig, R A Branch. Stereoselective metabolism and pharmacogenetic control of 5-phenyl-5-ethylhydantoin (nirvanol) in humans. The Journal of pharmacology and experimental therapeutics. 1984 Jul; 230(1):28-33. doi: NULL. [PMID: 6747829]
  • G Karlaganis, A Küpfer, J Bircher, U P Schlunegger, H Gfeller, P Bigler. Identification of mephenytoin metabolites in the dog. Drug metabolism and disposition: the biological fate of chemicals. 1980 May; 8(3):173-7. doi: NULL. [PMID: 6104582]