1-Hydroxymidazolam (BioDeep_00000408444)

   

natural product


代谢物信息卡片


α-Hydroxymidazolam

化学式: C18H13ClFN3O (341.07311300000003)
中文名称: 1-羟基咪达唑仑
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1C2=CN=C(N2C3=C(C=C(C=C3)Cl)C(=N1)C4=CC=CC=C4F)CO
InChI: InChI=1S/C18H13ClFN3O/c19-11-5-6-16-14(7-11)18(13-3-1-2-4-15(13)20)22-9-12-8-21-17(10-24)23(12)16/h1-8,24H,9-10H2

描述信息

An imidazobenzodiazepine that is midazolam in which one of the hydrogens of the methyl group is substituted by a hydroxy group. It is the major metabolite of the anesthetic, midazolam.
CONFIDENCE standard compound; INTERNAL_ID 2277

同义名列表

3 个代谢物同义名

1-Hydroxymidazolam; α-Hydroxymidazolam; Alpha-hydroxymidazolam



数据库引用编号

13 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

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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

  • Kaoru Toyama, Hidetoshi Furuie, Kana Kuroda, Tomoko Ishizuka, Yasuyuki Okuda, Takako Shimizu, Manabu Kato, Yoshiyuki Igawa, Yasuhiro Nishikawa, Hitoshi Ishizuka. Effects of Repeated Oral Administration of Esaxerenone on the Pharmacokinetics of Midazolam in Healthy Japanese Males. European journal of drug metabolism and pharmacokinetics. 2021 Sep; 46(5):685-694. doi: 10.1007/s13318-021-00701-4. [PMID: 34383278]
  • Iwona Zaporowska-Stachowiak, Tomasz Grabowski, Katarzyna Stachowiak-Szymczak, Karolina Gościniak, Artur Teżyk, Maciej Sopata. Midazolam and hydroxymidazolam plasma concentrations can be monitored with selected biochemical and physiological parameters of palliative care patients. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2021 May; 137(?):111304. doi: 10.1016/j.biopha.2021.111304. [PMID: 33550045]
  • Xin Wang, Ping Xiang, Olaf H Drummer, Jiaojiao Ji, Yue Zhuo, Gengli Duan, Min Shen. Pharmacokinetic study of midazolam and α-hydroxymidazolam in guinea pig blood and hair roots after a single dose of midazolam. Journal of pharmaceutical and biomedical analysis. 2021 Feb; 195(?):113890. doi: 10.1016/j.jpba.2021.113890. [PMID: 33454503]
  • Benjamin Berger, Priska Kaufmann, Annelize Koch, Jasper Dingemanse. Impact of the Selective Orexin-1 Receptor Antagonist ACT-539313 on the Pharmacokinetics of the CYP3A Probe Drug Midazolam in Healthy Male Subjects. Journal of clinical pharmacology. 2020 07; 60(7):931-941. doi: 10.1002/jcph.1588. [PMID: 32035014]
  • Patricia N Sidharta, Jasper Dingemanse. Effect of Multiple-Dose Aprocitentan Administration on the Pharmacokinetics of Midazolam in Healthy Male Subjects. European journal of drug metabolism and pharmacokinetics. 2020 Apr; 45(2):227-234. doi: 10.1007/s13318-019-00590-8. [PMID: 31773427]
  • Wei Zhou, Shuang-Long Li, Ti Zhao, Le Li, Wen-Bin Xing, Xiang-Jun Qiu, Wei Zhang. Effects of Dexmedetomidine on the Pharmacokinetics of Dezocine, Midazolam and Its Metabolite 1-Hydroxymidazolam in Beagles by UPLC-MS/MS. Drug design, development and therapy. 2020; 14(?):2595-2605. doi: 10.2147/dddt.s254055. [PMID: 32753841]
  • Jae Yong Park, Beom Jin Kim, Sang Wook Lee, Hyun Kang, Jeong Wook Kim, In-Jin Jang, Jae Gyu Kim. Influence of midazolam-related genetic polymorphism on conscious sedation during upper gastrointestinal endoscopy in a Korean population. Scientific reports. 2019 11; 9(1):16001. doi: 10.1038/s41598-019-52517-7. [PMID: 31690757]
  • Cédric B Larouche, Ron Johnson, Francis Beaudry, Craig Mosley, Yu Gu, Kristopher Afshaun Zaman, Hugues Beaufrère, Christopher Dutton. Pharmacokinetics of midazolam and its major metabolite 1-hydroxymidazolam in the ball python (Python regius) after intracardiac and intramuscular administrations. Journal of veterinary pharmacology and therapeutics. 2019 Nov; 42(6):722-731. doi: 10.1111/jvp.12806. [PMID: 31469454]
  • Bianca D van Groen, Wouter H Vaes, B Kevin Park, Elke H J Krekels, Esther van Duijn, Lenne-Triin Kõrgvee, Wioleta Maruszak, Grzegorz Grynkiewicz, R Colin Garner, Catherijne A J Knibbe, Dick Tibboel, Saskia N de Wildt, Mark A Turner. Dose-linearity of the pharmacokinetics of an intravenous [14 C]midazolam microdose in children. British journal of clinical pharmacology. 2019 10; 85(10):2332-2340. doi: 10.1111/bcp.14047. [PMID: 31269280]
  • Linda G Franken, Anniek D Masman, Brenda C M de Winter, Frans P M Baar, Dick Tibboel, Teun van Gelder, Birgit C P Koch, Ron A A Mathot. Hypoalbuminaemia and decreased midazolam clearance in terminally ill adult patients, an inflammatory effect?. British journal of clinical pharmacology. 2017 08; 83(8):1701-1712. doi: 10.1111/bcp.13259. [PMID: 28177137]
  • Alexander K Berg, Michael J Myrvik, Peter J Van Ess. Pharmacokinetics, pharmacodynamics, and tolerability of USL261, midazolam nasal spray: Randomized study in healthy geriatric and non-geriatric adults. Epilepsy & behavior : E&B. 2017 06; 71(Pt A):51-59. doi: 10.1016/j.yebeh.2017.02.023. [PMID: 28544992]
  • Lenneke Schrier, Rob Zuiker, Frans W H M Merkus, Erica S Klaassen, Zheng Guan, Bert Tuk, Joop M A van Gerven, Ronald van der Geest, Geert Jan Groeneveld. Pharmacokinetics and pharmacodynamics of a new highly concentrated intranasal midazolam formulation for conscious sedation. British journal of clinical pharmacology. 2017 04; 83(4):721-731. doi: 10.1111/bcp.13163. [PMID: 27780297]
  • Armel Stockis, Shikiko Watanabe, André J Scheen. Effect of brivaracetam on CYP3A activity, measured by oral midazolam. Journal of clinical pharmacology. 2015 May; 55(5):543-8. doi: 10.1002/jcph.446. [PMID: 25501671]
  • Regina V Oliveira, Jack Henion, Enaksha R Wickremsinhe. Automated high-capacity on-line extraction and bioanalysis of dried blood spot samples using liquid chromatography/high-resolution accurate mass spectrometry. Rapid communications in mass spectrometry : RCM. 2014 Nov; 28(22):2415-26. doi: 10.1002/rcm.7033. [PMID: 25303470]
  • Dorota Tomalik-Scharte, Ahmed Abbas Suleiman, Sebastian Frechen, Daria Kraus, Uta Kerkweg, Dennis Rokitta, Paola Di Gion, Christian Queckenberg, Uwe Fuhr. Population pharmacokinetic analysis of circadian rhythms in hepatic CYP3A activity using midazolam. Journal of clinical pharmacology. 2014 Oct; 54(10):1162-9. doi: 10.1002/jcph.318. [PMID: 24782075]
  • L Welzing, S Junghaenel, V Weiss, B Roth, C Mueller, M H J Wiesen. Disposition of midazolam in asphyxiated neonates receiving therapeutic hypothermia--a pilot study. Klinische Padiatrie. 2013 Dec; 225(7):398-404. doi: 10.1055/s-0033-1358749. [PMID: 24288267]
  • K D Mooiman, R F Maas-Bakker, H Rosing, J H Beijnen, J H M Schellens, I Meijerman. Development and validation of a LC-MS/MS method for the in vitro analysis of 1-hydroxymidazolam in human liver microsomes: application for determining CYP3A4 inhibition in complex matrix mixtures. Biomedical chromatography : BMC. 2013 Sep; 27(9):1107-16. doi: 10.1002/bmc.2913. [PMID: 23674377]
  • Shweta Urva, Emmanuel Bouillaud, Rosemary Delaney, Annette Jappe, Wing Cheung. A phase I study evaluating the effect of everolimus on the pharmacokinetics of midazolam in healthy subjects. Journal of clinical pharmacology. 2013 Apr; 53(4):444-50. doi: 10.1002/jcph.7. [PMID: 23426978]
  • Sara K Quinney, Srikar R Malireddy, Raj Vuppalanchi, Mitchell A Hamman, Naga Chalasani, J Christopher Gorski, Stephen D Hall. Rate of onset of inhibition of gut-wall and hepatic CYP3A by clarithromycin. European journal of clinical pharmacology. 2013 Mar; 69(3):439-48. doi: 10.1007/s00228-012-1339-x. [PMID: 22777148]
  • Ines Fuchs, Verena Hafner-Blumenstiel, Christoph Markert, Jürgen Burhenne, Johanna Weiss, Walter Emil Haefeli, Gerd Mikus. Effect of the CYP3A inhibitor ketoconazole on the PXR-mediated induction of CYP3A activity. European journal of clinical pharmacology. 2013 Mar; 69(3):507-13. doi: 10.1007/s00228-012-1388-1. [PMID: 22968811]
  • Varun Garg, Gurudatt Chandorkar, H Frank Farmer, Frances Smith, Katia Alves, Rolf P G van Heeswijk. Effect of telaprevir on the pharmacokinetics of midazolam and digoxin. Journal of clinical pharmacology. 2012 Oct; 52(10):1566-73. doi: 10.1177/0091270011419850. [PMID: 22162542]
  • Kai-Ming Duan, Sai-Ying Wang, Wen Ouyang, Yan-Mei Mao, Li-Jun Yang. Effect of quercetin on CYP3A activity in Chinese healthy participants. Journal of clinical pharmacology. 2012 Jun; 52(6):940-6. doi: 10.1177/0091270011406278. [PMID: 21680781]
  • Wei-Liang Li, Hua-Wen Xin, Mei-Wei Su. Inhibitory effects of continuous ingestion of Schisandrin A on CYP3A in the rat. Basic & clinical pharmacology & toxicology. 2012 Feb; 110(2):187-92. doi: 10.1111/j.1742-7843.2011.00787.x. [PMID: 21895978]
  • Camilla Svanström, Gunnar P Hansson, Leif D Svensson, Carl Johan Sennbro. Development and validation of a method using supported liquid extraction for the simultaneous determination of midazolam and 1'-hydroxy-midazolam in human plasma by liquid chromatography with tandem mass spectrometry detection. Journal of pharmaceutical and biomedical analysis. 2012 Jan; 58(?):71-7. doi: 10.1016/j.jpba.2011.09.015. [PMID: 21993197]
  • Henriette de Loor, Hylke de Jonge, Kristin Verbeke, Yves Vanrenterghem, Dirk R Kuypers. A highly sensitive liquid chromatography tandem mass spectrometry method for simultaneous quantification of midazolam, 1'-hydroxymidazolam and 4-hydroxymidazolam in human plasma. Biomedical chromatography : BMC. 2011 Oct; 25(10):1091-8. doi: 10.1002/bmc.1576. [PMID: 21204116]
  • Theo de Boer, Jaap Wieling, Erik Meulman, Mariska Reuvers, Gonda Renkema, Izaak den Daas, Thijs van Iersel, Johan Wemer, LingSing Chen. Application of dried blood spot sampling combined with LC-MS/MS for genotyping and phenotyping of CYP450 enzymes in healthy volunteers. Biomedical chromatography : BMC. 2011 Oct; 25(10):1112-23. doi: 10.1002/bmc.1580. [PMID: 21287583]
  • Leonie Fetzner, Jürgen Burhenne, Johanna Weiss, Michael Völker, Matthias Unger, Gerd Mikus, Walter Emil Haefeli. Daily honey consumption does not change CYP3A activity in humans. Journal of clinical pharmacology. 2011 Aug; 51(8):1223-32. doi: 10.1177/0091270010382022. [PMID: 21148046]
  • Ruut Kaartama, Pekka Jarho, Jouko Savolainen, Hannu Kokki, Marko Lehtonen. Determination of midazolam and 1-hydroxymidazolam from plasma by gas chromatography coupled to methane negative chemical ionization mass spectrometry after sublingual administration of midazolam. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Jun; 879(19):1668-76. doi: 10.1016/j.jchromb.2011.04.009. [PMID: 21531182]
  • Xinping Xue, Min Huang, Huanyu Xiao, Xiaoling Qin, Ling Huang, Guoping Zhong, Huichang Bi. Rapid and simultaneous measurement of midazolam, 1'-hydroxymidazolam and digoxin by liquid chromatography/tandem mass spectrometry: application to an in vivo study to simultaneously measure P-glycoprotein and cytochrome P450 3A activity. Journal of pharmaceutical and biomedical analysis. 2011 Apr; 55(1):187-93. doi: 10.1016/j.jpba.2011.01.018. [PMID: 21316177]
  • Kyung-Ah Seo, Soo Kyung Bae, Young-Kil Choi, Chang Soo Choi, Kwang-Hyeon Liu, Jae-Gook Shin. Metabolism of 1'- and 4-hydroxymidazolam by glucuronide conjugation is largely mediated by UDP-glucuronosyltransferases 1A4, 2B4, and 2B7. Drug metabolism and disposition: the biological fate of chemicals. 2010 Nov; 38(11):2007-13. doi: 10.1124/dmd.110.035295. [PMID: 20713656]
  • Stephanie Katzenmaier, Christoph Markert, Gerd Mikus. Proposal of a new limited sampling strategy to predict CYP3A activity using a partial AUC of midazolam. European journal of clinical pharmacology. 2010 Nov; 66(11):1137-41. doi: 10.1007/s00228-010-0878-2. [PMID: 20680253]
  • Miroslav Dostalek, Joyce S Macwan, Shripad D Chitnis, Ileana A Ionita, Fatemeh Akhlaghi. Development and validation of a rapid and sensitive assay for simultaneous quantification of midazolam, 1'-hydroxymidazolam, and 4-hydroxymidazolam by liquid chromatography coupled to tandem mass-spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2010 Jun; 878(19):1629-33. doi: 10.1016/j.jchromb.2010.04.001. [PMID: 20434409]
  • Maurice J Ahsman, Manon Hanekamp, Enno D Wildschut, Dick Tibboel, Ron A A Mathot. Population pharmacokinetics of midazolam and its metabolites during venoarterial extracorporeal membrane oxygenation in neonates. Clinical pharmacokinetics. 2010 Jun; 49(6):407-19. doi: 10.2165/11319970-000000000-00000. [PMID: 20481651]
  • Wei Zhang, Yan-Zi Chang, Quan-Cheng Kan, Li-Rong Zhang, Zhi-Song Li, Hui Lu, Zhong-Yu Wang, Qin-Jun Chu, Jie Zhang. CYP3A4*1G genetic polymorphism influences CYP3A activity and response to fentanyl in Chinese gynecologic patients. European journal of clinical pharmacology. 2010 Jan; 66(1):61-6. doi: 10.1007/s00228-009-0726-4. [PMID: 19784640]
  • Michael W Clarke, John R Burnett, Jason H Y Wu, Jonathan M Hodgson, Thomas Ledowski, Ian B Puddey, Kevin D Croft. Vitamin E supplementation and hepatic drug metabolism in humans. Journal of cardiovascular pharmacology. 2009 Dec; 54(6):491-6. doi: 10.1097/fjc.0b013e3181bfae18. [PMID: 19755916]
  • Thomas D Nolin, Reginald F Frye, Phuong Le, Hooman Sadr, Judith Naud, Francois A Leblond, Vincent Pichette, Jonathan Himmelfarb. ESRD impairs nonrenal clearance of fexofenadine but not midazolam. Journal of the American Society of Nephrology : JASN. 2009 Oct; 20(10):2269-76. doi: 10.1681/asn.2009010082. [PMID: 19696225]
  • Christophe Schmitt, Carsten Hofmann, Myriam Riek, Arpna Patel, Elke Zwanziger. Effect of saquinavir-ritonavir on cytochrome P450 3A4 activity in healthy volunteers using midazolam as a probe. Pharmacotherapy. 2009 Oct; 29(10):1175-81. doi: 10.1592/phco.29.10.1175. [PMID: 19792991]
  • Zhe-Yi Hu, Yuan-Sheng Zhao, Di Wu, Ze-Neng Cheng. Endogenous cortisol 6 beta-hydroxylation clearance is not an accurate probe for overall cytochrome P450 3A phenotyping in humans. Clinica chimica acta; international journal of clinical chemistry. 2009 Oct; 408(1-2):92-7. doi: 10.1016/j.cca.2009.07.017. [PMID: 19654004]
  • Xi Luo, Xiao-min Li, Zhe-yi Hu, Ze-neng Cheng. Evaluation of CYP3A activity in humans using three different parameters based on endogenous cortisol metabolism. Acta pharmacologica Sinica. 2009 Sep; 30(9):1323-9. doi: 10.1038/aps.2009.116. [PMID: 19701237]
  • Makiko Kokudai, Naoki Inui, Kazuhiko Takeuchi, Toshiyuki Sakaeda, Yoshiyuki Kagawa, Hiroshi Watanabe. Effects of statins on the pharmacokinetics of midazolam in healthy volunteers. Journal of clinical pharmacology. 2009 May; 49(5):568-73. doi: 10.1177/0091270009332435. [PMID: 19398603]
  • Xiu-Hua Ren, Lu-Qin Si, Lei Cao, Jie Yao, Jun Qiu, Gao Li. [Effect of polyoxyl ether analogous surfactants on the activity of cytochromes P450 3A in rats in vivo]. Yao xue xue bao = Acta pharmaceutica Sinica. 2008 May; 43(5):528-34. doi: NULL. [PMID: 18717343]
  • Martin F Fromm, Helmut Schwilden, Iouri Bachmakov, Jörg König, Frank Bremer, Jürgen Schüttler. Impact of the CYP3A5 genotype on midazolam pharmacokinetics and pharmacodynamics during intensive care sedation. European journal of clinical pharmacology. 2007 Dec; 63(12):1129-33. doi: 10.1007/s00228-007-0365-6. [PMID: 17786417]
  • Helen S Pentikis, Margaret Connolly, Carol B Trapnell, William P Forbes, Doug K Bettenhausen. The effect of multiple-dose, oral rifaximin on the pharmacokinetics of intravenous and oral midazolam in healthy volunteers. Pharmacotherapy. 2007 Oct; 27(10):1361-9. doi: 10.1592/phco.27.10.1361. [PMID: 17896891]
  • Wenkui Li, Suyi Luo, Harold T Smith, Francis L S Tse. Simultaneous determination of midazolam and 1'-hydroxymidazolam in human plasma by liquid chromatography with tandem mass spectrometry. Biomedical chromatography : BMC. 2007 Aug; 21(8):841-51. doi: 10.1002/bmc.829. [PMID: 17441219]
  • Mikiko Shimizu, Tsukasa Uno, Hiro-omi Tamura, Hideko Kanazawa, Isao Murakami, Kazunobu Sugawara, Tomonori Tateishi. A developed determination of midazolam and 1'-hydroxymidazolam in plasma by liquid chromatography-mass spectrometry: application of human pharmacokinetic study for measurement of CYP3A activity. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2007 Mar; 847(2):275-81. doi: 10.1016/j.jchromb.2006.10.018. [PMID: 17085083]
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