Oxazepam (BioDeep_00000017858)

 

Secondary id: BioDeep_00000001506

human metabolite Endogenous blood metabolite Chemicals and Drugs


代谢物信息卡片


7-chloro-3-hydroxy-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one

化学式: C15H11ClN2O2 (286.0509016)
中文名称: 奥沙西泮
谱图信息: 最多检出来源 Homo sapiens(blood) 15.79%

分子结构信息

SMILES: C1=CC=C(C=C1)C2=NC(C(=O)NC3=C2C=C(C=C3)Cl)O
InChI: InChI=1S/C15H11ClN2O2/c16-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)18-15(20)14(19)17-12/h1-8,15,20H,(H,17,19)

描述信息

Oxazepam is only found in individuals that have used or taken this drug. It is an intermediate-acting benzodiazepine used to treat alcohol withdrawal and anxiety disorders. It is a metabolite of diazepam, prazepam, temazepam, and clorazepate, and has moderate amnesic, anxiolytic, anticonvulsant, hypnotic, sedative, and skeletal muscle relaxant properties compared to other benzodiazepines (Wikipedia). Like other benzodiazepines, oxazepam exerts its anxiolytic effects by potentiating the effect of gamma-aminobutyric acid (GABA) on GABA-A receptors through a cooperative mechanism of action. GABA receptors are ionotropic chloride-linked channel receptors that produce inhibitory postsynaptic potentials. When activated by GABA, the GABA receptor/chloride ionophore complex undergoes a conformational change that allows the passage of chloride ions through the channel. Benzodiazepines are believed to exert their effect by increasing the effect of GABA at its receptor. Benzodiazepine binding increases chloride conductance in the presence of GABA by increasing the frequency at which the channel opens. In contrast, barbiturates increase chloride conductance in the presence of GABA by prolonging the time in which the channel remains open. There are 18 subtypes of the GABA receptor subunits. The α2 subunit of the α2β3γ2 receptor complex is thought to mediate anxiolytic effects while the α1 subunit of the α1β2γ2 receptor complex is thought to mediate sedative, anticonvulsant, and anterograde amnesia effects.
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives
D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014151 - Anti-Anxiety Agents
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents
N - Nervous system > N05 - Psycholeptics > N05B - Anxiolytics > N05BA - Benzodiazepine derivatives
C78272 - Agent Affecting Nervous System > C29756 - Sedative and Hypnotic > C1012 - Benzodiazepine
D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018757 - GABA Modulators
C78272 - Agent Affecting Nervous System > C28197 - Antianxiety Agent

同义名列表

13 个代谢物同义名

7-chloro-3-hydroxy-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one; 3-Hydroxynordiazepam; WY-3498oxozepam; (+-)-Oxazepam; (RS)-Oxazepam; Nortemazepam; Oxazipam; oxazepam; Adumbran; Oxozepam; Tazepam; ZAXOPAM; Serax



数据库引用编号

14 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

  • Anna Carfora, Carlo Pietro Campobasso, Paola Cassandro, Raffaella Petrella, Renata Borriello. Long-Term Detection in Hair of Zolpidem, Oxazepam and Flunitrazepam in a Case of Drug-Facilitated Sexual Assault. Journal of analytical toxicology. 2022 Feb; 46(1):e16-e20. doi: 10.1093/jat/bkaa174. [PMID: 33180140]
  • Fanny Varenne, Porkodi Kadhirvel, Pauline Bosman, Loïc Renault, Audrey Combès, Valérie Pichon. Synthesis and characterization of molecularly imprinted polymers for the selective extraction of oxazepam from complex environmental and biological samples. Analytical and bioanalytical chemistry. 2022 Jan; 414(1):451-463. doi: 10.1007/s00216-021-03268-w. [PMID: 33751162]
  • Daniel Cerveny, Jerker Fick, Jonatan Klaminder, Michael G Bertram, Tomas Brodin. Exposure via biotransformation: Oxazepam reaches predicted pharmacological effect levels in European perch after exposure to temazepam. Ecotoxicology and environmental safety. 2021 Jul; 217(?):112246. doi: 10.1016/j.ecoenv.2021.112246. [PMID: 33901781]
  • Luca Docci, Kenichi Umehara, Stephan Krähenbühl, Stephen Fowler, Neil Parrott. Construction and Verification of Physiologically Based Pharmacokinetic Models for Four Drugs Majorly Cleared by Glucuronidation: Lorazepam, Oxazepam, Naloxone, and Zidovudine. The AAPS journal. 2020 10; 22(6):128. doi: 10.1208/s12248-020-00513-5. [PMID: 33033903]
  • Gergő Dargó, Dávid Bajusz, Kristóf Simon, Judit Müller, György T Balogh. Human Serum Albumin Binding in a Vial: A Novel UV-pH Titration Method To Assist Drug Design. Journal of medicinal chemistry. 2020 02; 63(4):1763-1774. doi: 10.1021/acs.jmedchem.0c00046. [PMID: 31995375]
  • 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]
  • Zhipei Sang, Keren Wang, Pengfei Zhang, Jian Shi, Wenmin Liu, Zhenghuai Tan. Design, synthesis, in-silico and biological evaluation of novel chalcone derivatives as multi-function agents for the treatment of Alzheimer's disease. European journal of medicinal chemistry. 2019 Oct; 180(?):238-252. doi: 10.1016/j.ejmech.2019.07.021. [PMID: 31310916]
  • Zhipei Sang, Keren Wang, Jian Shi, Wenmin Liu, Zhenghuai Tan. Design, synthesis, in-silico and biological evaluation of novel chalcone-O-carbamate derivatives as multifunctional agents for the treatment of Alzheimer's disease. European journal of medicinal chemistry. 2019 Sep; 178(?):726-739. doi: 10.1016/j.ejmech.2019.06.026. [PMID: 31229875]
  • Erin S McCallum, Daniel Cerveny, Jerker Fick, Tomas Brodin. Slow-Release Implants for Manipulating Contaminant Exposures in Aquatic Wildlife: A New Tool for Field Ecotoxicology. Environmental science & technology. 2019 Jul; 53(14):8282-8290. doi: 10.1021/acs.est.9b01975. [PMID: 31067036]
  • Lina Dorthea Bruun, Kari Kjeldstadli, Vidar Temte, Morris Birdal, Liliana Bachs, Marit Langødegård, Dag Helge Strand, Kristin Irene Gaare, Elisabeth Øiestad, Gudrun Høiseth. Detection Time of Oxazepam and Zopiclone in Urine and Oral Fluid after Experimental Oral Dosing. Journal of analytical toxicology. 2019 Jun; 43(5):369-377. doi: 10.1093/jat/bky083. [PMID: 30615130]
  • Hongyan Liu, Xiaoming Qiang, Qing Song, Wei Li, Yuxi He, Chanyuan Ye, Zhenghuai Tan, Yong Deng. Discovery of 4'-OH-flurbiprofen Mannich base derivatives as potential Alzheimer's disease treatment with multiple inhibitory activities. Bioorganic & medicinal chemistry. 2019 03; 27(6):991-1001. doi: 10.1016/j.bmc.2019.01.040. [PMID: 30772129]
  • Qing Song, Yan Li, Zhongcheng Cao, Hongyan Liu, Chaoquan Tian, Ziyi Yang, Xiaoming Qiang, Zhenghuai Tan, Yong Deng. Discovery of novel 2,5-dihydroxyterephthalamide derivatives as multifunctional agents for the treatment of Alzheimer's disease. Bioorganic & medicinal chemistry. 2018 12; 26(23-24):6115-6127. doi: 10.1016/j.bmc.2018.11.015. [PMID: 30470598]
  • Reza Alizadeh, Maryam Salami, Shahram Seidi. A silica fiber coated with a ZnO-graphene oxide nanocomposite with high specific surface for use in solid phase microextraction of the antiepileptic drugs diazepam and oxazepam. Mikrochimica acta. 2018 06; 185(6):312. doi: 10.1007/s00604-018-2850-2. [PMID: 29860651]
  • Rui Xu, Ganyuan Xiao, Yan Li, Hongyan Liu, Qing Song, Xiaoyu Zhang, Ziyi Yang, Yunxiaozhu Zheng, Zhenghuai Tan, Yong Deng. Multifunctional 5,6-dimethoxybenzo[d]isothiazol-3(2H)-one-N-alkylbenzylamine derivatives with acetylcholinesterase, monoamine oxidases and β-amyloid aggregation inhibitory activities as potential agents against Alzheimer's disease. Bioorganic & medicinal chemistry. 2018 05; 26(8):1885-1895. doi: 10.1016/j.bmc.2018.02.037. [PMID: 29500132]
  • Zhongcheng Cao, Jie Yang, Rui Xu, Qin Song, Xiaoyu Zhang, Hongyan Liu, Xiaoming Qiang, Yan Li, Zhenghuai Tan, Yong Deng. Design, synthesis and evaluation of 4'-OH-flurbiprofen-chalcone hybrids as potential multifunctional agents for Alzheimer's disease treatment. Bioorganic & medicinal chemistry. 2018 03; 26(5):1102-1115. doi: 10.1016/j.bmc.2018.01.030. [PMID: 29409707]
  • V Bugelli, L Papi, S Fornaro, F Stefanelli, S Chericoni, M Giusiani, S Vanin, C P Campobasso. Entomotoxicology in burnt bodies: a case of maternal filicide-suicide by fire. International journal of legal medicine. 2017 Sep; 131(5):1299-1306. doi: 10.1007/s00414-017-1628-0. [PMID: 28691148]
  • Philippine Granger Joly de Boissel, Patrice Gonzalez, Audrey Buleté, Guillemine Daffe, Christelle Clérandeau, Emmanuelle Vulliet, Jérôme Cachot. An innovative and integrative assay for toxicity testing using individual fish embryos. Application to oxazepam. Chemosphere. 2017 Aug; 181(?):468-477. doi: 10.1016/j.chemosphere.2017.04.067. [PMID: 28460293]
  • Souleiman El Balkhi, Maxime Chaslot, Nicolas Picard, Sylvain Dulaurent, Martine Delage, Olivier Mathieu, Franck Saint-Marcoux. Characterization and identification of eight designer benzodiazepine metabolites by incubation with human liver microsomes and analysis by a triple quadrupole mass spectrometer. International journal of legal medicine. 2017 Jul; 131(4):979-988. doi: 10.1007/s00414-017-1541-6. [PMID: 28160051]
  • Paula Melo, Pedro Costa, Maria José Quintas, André Castro, Sónia Tarelho, João Miguel Franco, Helena M Teixeira. Pentobarbital in the context of possible suicides: Analysis of a Case. Forensic science international. 2017 May; 274(?):109-112. doi: 10.1016/j.forsciint.2016.11.042. [PMID: 28007369]
  • Zhipei Sang, Wanli Pan, Keren Wang, Qinge Ma, Lintao Yu, Yan Yang, Ping Bai, Chaoliang Leng, Qian Xu, Xiaoqing Li, Zhenghuai Tan, Wenmin Liu. Design, synthesis and evaluation of novel ferulic acid-O-alkylamine derivatives as potential multifunctional agents for the treatment of Alzheimer's disease. European journal of medicinal chemistry. 2017 Apr; 130(?):379-392. doi: 10.1016/j.ejmech.2017.02.039. [PMID: 28279845]
  • Li Luo, Yan Li, Xiaoming Qiang, Zhongcheng Cao, Rui Xu, Xia Yang, Ganyuan Xiao, Qing Song, Zhenghuai Tan, Yong Deng. Multifunctional thioxanthone derivatives with acetylcholinesterase, monoamine oxidases and β-amyloid aggregation inhibitory activities as potential agents against Alzheimer's disease. Bioorganic & medicinal chemistry. 2017 03; 25(6):1997-2009. doi: 10.1016/j.bmc.2017.02.027. [PMID: 28237559]
  • Stefania Salvatore, Jo Røislien, Jose A Baz-Lomba, Jørgen G Bramness. Assessing prescription drug abuse using functional principal component analysis (FPCA) of wastewater data. Pharmacoepidemiology and drug safety. 2017 Mar; 26(3):320-326. doi: 10.1002/pds.4127. [PMID: 27862608]
  • Courtney M Keller, Kelly N Breaux, Nicholas E Goeders. Effects of the combination of metyrapone and oxazepam on cocaine-induced increases in corticosterone in the medial prefrontal cortex and nucleus accumbens. Psychoneuroendocrinology. 2017 03; 77(?):75-83. doi: 10.1016/j.psyneuen.2016.12.004. [PMID: 28024272]
  • Xiaoming Qiang, Yan Li, Xia Yang, Li Luo, Rui Xu, Yunxiaozhu Zheng, Zhongcheng Cao, Zhenghuai Tan, Yong Deng. DL-3-n-butylphthalide-Edaravone hybrids as novel dual inhibitors of amyloid-β aggregation and monoamine oxidases with high antioxidant potency for Alzheimer's therapy. Bioorganic & medicinal chemistry letters. 2017 02; 27(4):718-722. doi: 10.1016/j.bmcl.2017.01.050. [PMID: 28131710]
  • Yan Li, Xiaoming Qiang, Li Luo, Xia Yang, Ganyuan Xiao, Qi Liu, Jiachen Ai, Zhenghuai Tan, Yong Deng. Aurone Mannich base derivatives as promising multifunctional agents with acetylcholinesterase inhibition, anti-β-amyloid aggragation and neuroprotective properties for the treatment of Alzheimer's disease. European journal of medicinal chemistry. 2017 Jan; 126(?):762-775. doi: 10.1016/j.ejmech.2016.12.009. [PMID: 27951485]
  • Belinda Huerta, Luigi Margiotta-Casaluci, Sara Rodríguez-Mozaz, Martin Scholze, Matthew J Winter, Damià Barceló, John P Sumpter. Anti-anxiety drugs and fish behavior: Establishing the link between internal concentrations of oxazepam and behavioral effects. Environmental toxicology and chemistry. 2016 11; 35(11):2782-2790. doi: 10.1002/etc.3448. [PMID: 27061599]
  • Yan Li, Xiaoming Qiang, Li Luo, Yuxing Li, Ganyuan Xiao, Zhenghuai Tan, Yong Deng. Synthesis and evaluation of 4-hydroxyl aurone derivatives as multifunctional agents for the treatment of Alzheimer's disease. Bioorganic & medicinal chemistry. 2016 05; 24(10):2342-51. doi: 10.1016/j.bmc.2016.04.012. [PMID: 27079124]
  • Bruce Imbert, Amélie Marsot, Natalia Liachenko, Nicolas Simon. Population Pharmacokinetics of High-Dose Oxazepam in Alcohol-Dependent Patients: Is There a Risk of Accumulation?. Therapeutic drug monitoring. 2016 Apr; 38(2):253-8. doi: 10.1097/ftd.0000000000000262. [PMID: 26580099]
  • Christopher D Schmoutz, Glenn F Guerin, Scott P Runyon, Suraj Dhungana, Nicholas E Goeders. A therapeutic combination of metyrapone and oxazepam increases brain levels of GABA-active neurosteroids and decreases cocaine self-administration in male rats. Behavioural brain research. 2015 Sep; 291(?):108-111. doi: 10.1016/j.bbr.2015.05.019. [PMID: 26003946]
  • Zhipei Sang, Yan Li, Xiaoming Qiang, Ganyuan Xiao, Qiang Liu, Zhenghuai Tan, Yong Deng. Multifunctional scutellarin-rivastigmine hybrids with cholinergic, antioxidant, biometal chelating and neuroprotective properties for the treatment of Alzheimer's disease. Bioorganic & medicinal chemistry. 2015 Feb; 23(4):668-80. doi: 10.1016/j.bmc.2015.01.005. [PMID: 25614117]
  • Wen C Shan, Ya L Cui, Xin He, Lei Zhang, Jing Liu, Jian P Wang. Production of monoclonal antibody against clonazepam for immunoassay of benzodiazepine drugs in swine tissues. Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes. 2015; 50(1):15-22. doi: 10.1080/03601234.2015.964620. [PMID: 25421624]
  • Sabine Klein, Marion Bankstahl, Martina Gramer, Maria Hausknecht, Wolfgang Löscher. Low doses of ethanol markedly potentiate the anti-seizure effect of diazepam in a mouse model of difficult-to-treat focal seizures. Epilepsy research. 2014 Dec; 108(10):1719-27. doi: 10.1016/j.eplepsyres.2014.10.002. [PMID: 25458535]
  • Ayodele A Morris, Scot A Chester, Erin C Strickland, Gregory L McIntire. Rapid enzymatic hydrolysis using a novel recombinant β-glucuronidase in benzodiazepine urinalysis. Journal of analytical toxicology. 2014 Oct; 38(8):610-4. doi: 10.1093/jat/bku083. [PMID: 25217555]
  • Elisabetta Bertol, Francesco Mari, Rafael Boscolo Berto, Guido Mannaioni, Fabio Vaiano, Donata Favretto. A mixed MDPV and benzodiazepine intoxication in a chronic drug abuser: determination of MDPV metabolites by LC-HRMS and discussion of the case. Forensic science international. 2014 Oct; 243(?):149-55. doi: 10.1016/j.forsciint.2014.08.002. [PMID: 25199615]
  • Glenn F Guerin, Christopher D Schmoutz, Nicholas E Goeders. The extra-adrenal effects of metyrapone and oxazepam on ongoing cocaine self-administration. Brain research. 2014 Aug; 1575(?):45-54. doi: 10.1016/j.brainres.2014.05.039. [PMID: 24887642]
  • André Mateus, Pär Matsson, Per Artursson. A high-throughput cell-based method to predict the unbound drug fraction in the brain. Journal of medicinal chemistry. 2014 Apr; 57(7):3005-10. doi: 10.1021/jm401963n. [PMID: 24601604]
  • Samantha Luk, Rabia S Atayee, Joseph D Ma, Brookie M Best. Urinary diazepam metabolite distribution in a chronic pain population. Journal of analytical toxicology. 2014 Apr; 38(3):135-42. doi: 10.1093/jat/bku001. [PMID: 24500275]
  • Brittany Malik-Wolf, Shawn Vorce, Justin Holler, Thomas Bosy. Evaluation of abalone β-glucuronidase substitution in current urine hydrolysis procedures. Journal of analytical toxicology. 2014 Apr; 38(3):171-6. doi: 10.1093/jat/bku003. [PMID: 24488113]
  • Nicholas E Goeders, Glenn F Guerin, Christopher D Schmoutz. The combination of metyrapone and oxazepam for the treatment of cocaine and other drug addictions. Advances in pharmacology (San Diego, Calif.). 2014; 69(?):419-79. doi: 10.1016/b978-0-12-420118-7.00011-1. [PMID: 24484984]
  • Courtney M Keller, Elyse M Cornett, Glenn F Guerin, Nicholas E Goeders. Combinations of oxazepam and metyrapone attenuate cocaine and methamphetamine cue reactivity. Drug and alcohol dependence. 2013 Dec; 133(2):405-12. doi: 10.1016/j.drugalcdep.2013.06.025. [PMID: 23896309]
  • Alfredo Carlo Altamura, Donatella Moliterno, Silvia Paletta, Michele Maffini, Massimo Carlo Mauri, Silvio Bareggi. Understanding the pharmacokinetics of anxiolytic drugs. Expert opinion on drug metabolism & toxicology. 2013 Apr; 9(4):423-40. doi: 10.1517/17425255.2013.759209. [PMID: 23330992]
  • J Sarris, E Laporte, A Scholey, R King, A Pipingas, I Schweitzer, C Stough. Does a medicinal dose of kava impair driving? A randomized, placebo-controlled, double-blind study. Traffic injury prevention. 2013; 14(1):13-7. doi: 10.1080/15389588.2012.682233. [PMID: 23259514]
  • Stephanie J Marin, Mark Roberts, Michelle Wood, Gwendolyn A McMillin. Sensitive UPLC-MS-MS assay for 21 benzodiazepine drugs and metabolites, zolpidem and zopiclone in serum or plasma. Journal of analytical toxicology. 2012 Sep; 36(7):472-6. doi: 10.1093/jat/bks059. [PMID: 22833647]
  • Anita S Kablinger, Marie A Lindner, Stephanie Casso, Franz Hefti, George DeMuth, Barbara S Fox, Lindsay A McNair, Bruce G McCarthy, Nicholas E Goeders. Effects of the combination of metyrapone and oxazepam on cocaine craving and cocaine taking: a double-blind, randomized, placebo-controlled pilot study. Journal of psychopharmacology (Oxford, England). 2012 Jul; 26(7):973-81. doi: 10.1177/0269881111430745. [PMID: 22236504]
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  • Ahad Bavili Tabrizi, Maryam Harasi. Applying cloud point extraction technique for the extraction of oxazepam from human urine as a colour or fluorescent derivative prior to spectroscopic analysis methods. Drug testing and analysis. 2012 Feb; 4(2):145-50. doi: 10.1002/dta.259. [PMID: 21381221]
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