5-Hydroxyomeprazole (BioDeep_00000017944)

   

human metabolite Endogenous blood metabolite


代谢物信息卡片


(4-methoxy-6-{[(6-methoxy-1H-1,3-benzodiazol-2-yl)sulfinyl]methyl}-5-methylpyridin-3-yl)methanol

化学式: C17H19N3O4S (361.10962140000004)
中文名称: 5-羟基奥美拉唑
谱图信息: 最多检出来源 Homo sapiens(blood) 39.89%

分子结构信息

SMILES: CC1=C(C(=CN=C1CS(=O)C2=NC3=C(N2)C=C(C=C3)OC)CO)OC
InChI: InChI=1S/C17H19N3O4S/c1-10-15(18-7-11(8-21)16(10)24-3)9-25(22)17-19-13-5-4-12(23-2)6-14(13)20-17/h4-7,21H,8-9H2,1-3H3,(H,19,20)

描述信息

5-Hydroxyomeprazole is only found in individuals that have used or taken Omeprazole. 5-Hydroxyomeprazole is a metabolite of Omeprazole. 5-hydroxyomeprazole belongs to the family of Sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.

同义名列表

8 个代谢物同义名

(4-methoxy-6-{[(6-methoxy-1H-1,3-benzodiazol-2-yl)sulfinyl]methyl}-5-methylpyridin-3-yl)methanol; 5-Methoxy-2-(((4-methoxy-3-methyl-5-hydroxymethyl-2-pyridinyl)methyl)sulphinyl)-1H-benzimidazole; 5-Methoxy-2-(((4-methoxy-3-methyl-5-hydroxymethyl-2-pyridinyl)methyl)sulfinyl)-1H-benzimidazole; {4-methoxy-6-[(5-methoxy-3H-1,3-benzodiazol-2-ylsulfinyl)methyl]-5-methylpyridin-3-yl}methanol; 5-Hydroxymethylomeprazole; 5-HYDROXY OMEPRAZOLE; 5-HYDROXYOMEPRAZOLE; Hydroxyomeprazole



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(5)

BioCyc(0)

PlantCyc(0)

代谢反应

51 个相关的代谢反应过程信息。

Reactome(50)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(1)

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

  • Lateef Ahmad, Zafar Iqbal, Yasar Shah, Shabnam Nazir, Abad Khan, Muhammad Imran Khan, Abbas Khan, Fazli Khuda, Ismail Khan. Comparative pharmacokinetics of Omeprazole and its metabolites in poor and extensive metabolizer Pakistani healthy volunteers and a review of different studies. Pakistan journal of pharmaceutical sciences. 2018 Jul; 31(4):1363-1374. doi: . [PMID: 30033421]
  • Maryam Payan, Mohammad Reza Rouini, Nader Tajik, Mohammad Hossein Ghahremani, Reza Tahvilian. Hydroxylation index of omeprazole in relation to CYP2C19 polymorphism and sex in a healthy Iranian population. Daru : journal of Faculty of Pharmacy, Tehran University of Medical Sciences. 2014 Dec; 22(?):81. doi: 10.1186/s40199-014-0081-6. [PMID: 25498969]
  • Rasmus S Pedersen, Lene Noehr-Jensen, Kim Brosen. Inhibitory effect of oral contraceptives on CYP2C19 activity is not significant in carriers of the CYP2C19*17 allele. Clinical and experimental pharmacology & physiology. 2013 Oct; 40(10):683-8. doi: 10.1111/1440-1681.12153. [PMID: 23844835]
  • Maryam Noubarani, Farzad Kobarfard, Manijeh Motevalian, Fariborz Keyhanfar. Variation in omeprazole pharmacokinetics in a random Iranian population: a pilot study. Biopharmaceutics & drug disposition. 2012 Sep; 33(6):324-31. doi: 10.1002/bdd.1805. [PMID: 22890488]
  • Kyung-Suk Oh, Su-Jin Park, Dhananjay D Shinde, Jae-Gook Shin, Dong-Hyun Kim. High-sensitivity liquid chromatography-tandem mass spectrometry for the simultaneous determination of five drugs and their cytochrome P450-specific probe metabolites in human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 May; 895-896(?):56-64. doi: 10.1016/j.jchromb.2012.03.014. [PMID: 22483397]
  • Ersin Gumus, Ozgur Karaca, Melih O Babaoglu, Gökhan Baysoy, Necati Balamtekin, Hulya Demir, Nuray Uslu, Atilla Bozkurt, Aysel Yuce, Umit Yasar. Evaluation of lansoprazole as a probe for assessing cytochrome P450 2C19 activity and genotype-phenotype correlation in childhood. European journal of clinical pharmacology. 2012 May; 68(5):629-36. doi: 10.1007/s00228-011-1151-z. [PMID: 22076562]
  • Eileen B Lawson, Jerry C Wu, R Michael Baldwin, Magnus Ingelman-Sundberg, Staffan Rosenborg, Dong-Seok Yim, Ophelia Q P Yin, Edmund V Capparelli, Joseph D Ma. Omeprazole limited sampling strategies to predict area under the concentration-time curve ratios: implications for cytochrome P450 2C19 and 3A phenotyping. European journal of clinical pharmacology. 2012 Apr; 68(4):407-13. doi: 10.1007/s00228-011-1136-y. [PMID: 22009190]
  • Xiang-Yang Li, Yong-Nian Liu, Ming Yuan, Yong-Ping Li, Ying-Zhong Yang, Jun-Bo Zhu. [Effect of high altitude hypoxia on the activity and protein expression of CYP2C9 and CYP2C19]. Yao xue xue bao = Acta pharmaceutica Sinica. 2012 Feb; 47(2):188-93. doi: NULL. [PMID: 22512029]
  • Justin D Lutz, Nina Isoherranen. Prediction of relative in vivo metabolite exposure from in vitro data using two model drugs: dextromethorphan and omeprazole. Drug metabolism and disposition: the biological fate of chemicals. 2012 Jan; 40(1):159-68. doi: 10.1124/dmd.111.042200. [PMID: 22010218]
  • Hideo Shiohira, Norio Yasui-Furukori, Tomonori Tateishi, Tsukasa Uno. Chiral assay of omeprazole and metabolites and its application to a pharmacokinetics related to CYP2C19 genotypes. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Aug; 879(24):2465-70. doi: 10.1016/j.jchromb.2011.06.046. [PMID: 21783435]
  • S Rosenborg, M Stenberg, S Otto, J Ostervall, M Masquelier, Q-Y Yue, L Bertilsson, E Eliasson. Clinically significant CYP2C inhibition by noscapine but not by glucosamine. Clinical pharmacology and therapeutics. 2010 Sep; 88(3):343-6. doi: 10.1038/clpt.2010.107. [PMID: 20668444]
  • S K Jin, T S Kang, S O Eom, J-I Kim, H J Lee, J Roh. CYP2C19 haplotypes in Koreans as a marker of enzyme activity evaluated with omeprazole. Journal of clinical pharmacy and therapeutics. 2009 Aug; 34(4):437-46. doi: 10.1111/j.1365-2710.2008.01012.x. [PMID: 19583677]
  • B L Chen, Y Chen, J H Tu, Y L Li, W Zhang, Q Li, L Fan, Z R Tan, D L Hu, D Wang, L S Wang, D S Ouyang, H H Zhou. Clopidogrel inhibits CYP2C19-dependent hydroxylation of omeprazole related to CYP2C19 genetic polymorphisms. Journal of clinical pharmacology. 2009 May; 49(5):574-81. doi: 10.1177/0091270009333016. [PMID: 19398604]
  • Takenori Niioka, Tsukasa Uno, Katsuyoshi Sugimoto, Kazunobu Sugawara, Makoto Hayakari, Tomonori Tateishi. Estimation of CYP2C19 activity by the omeprazole hydroxylation index at a single point in time after intravenous and oral administration. European journal of clinical pharmacology. 2007 Nov; 63(11):1031-8. doi: 10.1007/s00228-007-0331-3. [PMID: 17701405]
  • Lan Fan, Guo Wang, Lian-Sheng Wang, Yao Chen, Wei Zhang, Yuan-Fei Huang, Rui-Xue Huang, Dong-Li Hu, Dan Wang, Hong-Hao Zhou. Herbal medicine yin zhi huang induces CYP3A4-mediated sulfoxidation and CYP2C19-dependent hydroxylation of omeprazole. Acta pharmacologica Sinica. 2007 Oct; 28(10):1685-92. doi: 10.1111/j.1745-7254.2007.00617.x. [PMID: 17883958]
  • Jiu-Hui Wang, Pei-Qiong Li, Qiong-Yao Fu, Qiu-Xiang Li, Wang-Wei Cai. Cyp2c19 genotype and omeprazole hydroxylation phenotype in Chinese Li population. Clinical and experimental pharmacology & physiology. 2007 May; 34(5-6):421-4. doi: 10.1111/j.1440-1681.2007.04583.x. [PMID: 17439410]
  • Tomás Pérez-Ruiz, Carmen Martínez-Lozano, A Sanz, E Bravo, Raquel Galera. Determination of omeprazole, hydroxyomeprazole and omeprazole sulfone using automated solid phase extraction and micellar electrokinetic capillary chromatography. Journal of pharmaceutical and biomedical analysis. 2006 Sep; 42(1):100-6. doi: 10.1016/j.jpba.2005.09.029. [PMID: 16280228]
  • Qi Song, Weng Naidong. Analysis of omeprazole and 5-OH omeprazole in human plasma using hydrophilic interaction chromatography with tandem mass spectrometry (HILIC-MS/MS)--eliminating evaporation and reconstitution steps in 96-well liquid/liquid extraction. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 Jan; 830(1):135-42. doi: 10.1016/j.jchromb.2005.10.042. [PMID: 16298175]
  • Matthias Schwab, Ulrich Klotz, Ute Hofmann, Elke Schaeffeler, Andreas Leodolter, Peter Malfertheiner, Gerhard Treiber. Esomeprazole-induced healing of gastroesophageal reflux disease is unrelated to the genotype of CYP2C19: evidence from clinical and pharmacokinetic data. Clinical pharmacology and therapeutics. 2005 Dec; 78(6):627-34. doi: 10.1016/j.clpt.2005.08.017. [PMID: 16338278]
  • Valerie A Frerichs, Colleen Zaranek, Curtis E Haas. Analysis of omeprazole, midazolam and hydroxy-metabolites in plasma using liquid chromatography coupled to tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2005 Sep; 824(1-2):71-80. doi: 10.1016/j.jchromb.2005.07.001. [PMID: 16027049]
  • Yukio Ishizawa, Norio Yasui-Furukori, Takenori Takahata, Mutsuo Sasaki, Tomonori Tateishi. The effect of aging on the relationship between the cytochrome P450 2C19 genotype and omeprazole pharmacokinetics. Clinical pharmacokinetics. 2005; 44(11):1179-89. doi: 10.2165/00003088-200544110-00005. [PMID: 16231968]
  • Hyung-Keun Roh, Pum-Soo Kim, Don-Haeng Lee, Gunnel Tybring, Mohamed Sagar, Chang-Shin Park, Rein Seensalu, Leif Bertilsson. Omeprazole treatment of Korean patients: effects on gastric pH and gastrin release in relation to CYP2C19 geno- and phenotypes. Basic & clinical pharmacology & toxicology. 2004 Sep; 95(3):112-9. doi: 10.1111/j.1742-7843.2004.950302.x. [PMID: 15447734]
  • Ophelia Q P Yin, Brian Tomlinson, Albert H L Chow, Mary M Y Waye, Moses S S Chow. Omeprazole as a CYP2C19 marker in Chinese subjects: assessment of its gene-dose effect and intrasubject variability. Journal of clinical pharmacology. 2004 Jun; 44(6):582-9. doi: 10.1177/0091270004265702. [PMID: 15145965]
  • W Tassaneeyakul, S Vannaprasaht, Y Yamazoe. Formation of omeprazole sulphone but not 5-hydroxyomeprazole is inhibited by grapefruit juice. British journal of clinical pharmacology. 2000 Feb; 49(2):139-44. doi: 10.1046/j.1365-2125.2000.00122.x. [PMID: 10671908]
  • G García-Encina, R Farrán, S Puig, L Martínez. Validation of an automated liquid chromatographic method for omeprazole in human plasma using on-line solid-phase extraction. Journal of pharmaceutical and biomedical analysis. 1999 Nov; 21(2):371-82. doi: 10.1016/s0731-7085(99)00178-8. [PMID: 10703993]
  • E J Woolf, B K Matuszewski. Simultaneous determination of omeprazole and 5'-hydroxyomeprazole in human plasma by liquid chromatography-tandem mass spectrometry. Journal of chromatography. A. 1998 Dec; 828(1-2):229-38. doi: 10.1016/s0021-9673(98)00790-0. [PMID: 9916309]
  • U S Svensson, M Ashton, N H Trinh, L Bertilsson, X H Dinh, V H Nguyen, T N Nguyen, D S Nguyen, J Lykkesfeldt, D C Le. Artemisinin induces omeprazole metabolism in human beings. Clinical pharmacology and therapeutics. 1998 Aug; 64(2):160-7. doi: 10.1016/s0009-9236(98)90149-7. [PMID: 9728896]
  • G Tybring, Y Böttiger, J Widén, L Bertilsson. Enantioselective hydroxylation of omeprazole catalyzed by CYP2C19 in Swedish white subjects. Clinical pharmacology and therapeutics. 1997 Aug; 62(2):129-37. doi: 10.1016/s0009-9236(97)90060-6. [PMID: 9284848]
  • K L Rost, I Roots. Nonlinear kinetics after high-dose omeprazole caused by saturation of genetically variable CYP2C19. Hepatology (Baltimore, Md.). 1996 Jun; 23(6):1491-7. doi: 10.1002/hep.510230628. [PMID: 8675169]
  • I Ieiri, T Kubota, A Urae, M Kimura, Y Wada, K Mamiya, S Yoshioka, S Irie, T Amamoto, K Nakamura, S Nakano, S Higuchi. Pharmacokinetics of omeprazole (a substrate of CYP2C19) and comparison with two mutant alleles, C gamma P2C19m1 in exon 5 and C gamma P2C19m2 in exon 4, in Japanese subjects. Clinical pharmacology and therapeutics. 1996 Jun; 59(6):647-53. doi: 10.1016/s0009-9236(96)90004-1. [PMID: 8681489]
  • M Chang, M L Dahl, G Tybring, E Götharson, L Bertilsson. Use of omeprazole as a probe drug for CYP2C19 phenotype in Swedish Caucasians: comparison with S-mephenytoin hydroxylation phenotype and CYP2C19 genotype. Pharmacogenetics. 1995 Dec; 5(6):358-63. doi: 10.1097/00008571-199512000-00004. [PMID: 8747407]
  • M Chang, G Tybring, M L Dahl, E Götharson, M Sagar, R Seensalu, L Bertilsson. Interphenotype differences in disposition and effect on gastrin levels of omeprazole--suitability of omeprazole as a probe for CYP2C19. British journal of clinical pharmacology. 1995 May; 39(5):511-8. doi: 10.1111/j.1365-2125.1995.tb04488.x. [PMID: 7669487]
  • D R Sohn, K Kobayashi, K Chiba, K H Lee, S G Shin, T Ishizaki. Disposition kinetics and metabolism of omeprazole in extensive and poor metabolizers of S-mephenytoin 4'-hydroxylation recruited from an Oriental population. The Journal of pharmacology and experimental therapeutics. 1992 Sep; 262(3):1195-202. doi: NULL. [PMID: 1527724]
  • C G Regårdh, T Andersson, P O Lagerström, P Lundborg, I Skånberg. The pharmacokinetics of omeprazole in humans--a study of single intravenous and oral doses. Therapeutic drug monitoring. 1990 Mar; 12(2):163-72. doi: 10.1097/00007691-199003000-00010. [PMID: 2315973]
  • L Renberg, R Simonsson, K J Hoffmann. Identification of two main urinary metabolites of [14C]omeprazole in humans. Drug metabolism and disposition: the biological fate of chemicals. 1989 Jan; 17(1):69-76. doi: NULL. [PMID: 2566473]
  • J Naesdal, T Andersson, G Bodemar, R Larsson, C G Regårdh, I Skånberg, A Walan. Pharmacokinetics of [14C]omeprazole in patients with impaired renal function. Clinical pharmacology and therapeutics. 1986 Sep; 40(3):344-51. doi: 10.1038/clpt.1986.186. [PMID: 3742939]