Nordiazepam (BioDeep_00000002111)

 

Secondary id: BioDeep_00000397515

human metabolite Endogenous blood metabolite Chemicals and Drugs


代谢物信息卡片


7-Chloro-1,3-dihydro-5-phenyl-(2H)-1,4-benzodiazepin-2-one

化学式: C15H11ClN2O (270.0559866)
中文名称: 去甲西泮
谱图信息: 最多检出来源 Homo sapiens(blood) 1.78%

分子结构信息

SMILES: C1C(=O)NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3
InChI: InChI=1S/C15H11ClN2O/c16-11-6-7-13-12(8-11)15(17-9-14(19)18-13)10-4-2-1-3-5-10/h1-8H,9H2,(H,18,19)

描述信息

N-demethyldiazepam, also known as nordiazepam or calmday, is a member of the class of compounds known as 1,4-benzodiazepines. 1,4-benzodiazepines are organic compounds containing a benzene ring fused to a 1,4-azepine. N-demethyldiazepam is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). N-demethyldiazepam can be found in common wheat, corn, and potato, which makes N-demethyldiazepam a potential biomarker for the consumption of these food products. N-demethyldiazepam can be found primarily in blood and urine, as well as in human kidney and liver tissues. N-demethyldiazepam is a non-carcinogenic (not listed by IARC) potentially toxic compound. General supportive measures should be employed, along with intravenous fluids, and an adequate airway maintained. Hypotension may be combated by the use of norepinephrine or metaraminol. Dialysis is of limited value. Flumazenil (Anexate) is a competitive benzodiazepine receptor antagonist that can be used as an antidote for benzodiazepine overdose. In particular, flumazenil is very effective at reversing the CNS depression associated with benzodiazepines but is less effective at reversing respiratory depression. Its use, however, is controversial as it has numerous contraindications. It is contraindicated in patients who are on long-term benzodiazepines, those who have ingested a substance that lowers the seizure threshold, or in patients who have tachycardia or a history of seizures. As a general rule, medical observation and supportive care are the mainstay of treatment of benzodiazepine overdose. Although benzodiazepines are absorbed by activated charcoal, gastric decontamination with activated charcoal is not beneficial in pure benzodiazepine overdose as the risk of adverse effects often outweigh any potential benefit from the procedure. It is recommended only if benzodiazepines have been taken in combination with other drugs that may benefit from decontamination. Gastric lavage (stomach pumping) or whole bowel irrigation are also not recommended (T3DB).
Nordiazepam is a metabolite of Diazepam. Diazepam, first marketed as Valium by Hoffmann-La Roche, is a benzodiazepine drug. Nordazepam, also known as desoxydemoxepam, nordiazepam and desmethyldiazepam, is a 1,4-benzodiazepine derivative. Like other benzodiazepine derivatives, it has anticonvulsant, anxiolytic, muscle relaxant and sedative properties. (Wikipedia)
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
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants
D018377 - Neurotransmitter Agents > D018682 - GABA Agents > D018757 - GABA Modulators
C78272 - Agent Affecting Nervous System > C28197 - Antianxiety Agent
CONFIDENCE standard compound; EAWAG_UCHEM_ID 3608

同义名列表

31 个代谢物同义名

7-Chloro-1,3-dihydro-5-phenyl-(2H)-1,4-benzodiazepin-2-one; 7-Chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one; 7-Chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one; 7-chloro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one; N-Desmethyldiazepam (Nordazepam); N Descyclopropylmethyl prazepam; N-Descyclopropylmethyl-prazepam; N-Descyclopropylmethylprazepam; N Descyclopropylmethylprazepam; N-Destrifluoroethylhalazepam; N Destrifluoroethylhalazepam; Chlordesmethyldiazepam; N1-Desmethyldiazepam; N-Desalkylhalazepam; N Desalkylhalazepam; N-Desmethyldiazepam; 1-Demethyldiazepam; N-Demethyldiazepam; Desmethyldiazepam; N-Deoxydemoxepam; Demethyldiazepam; Dealkylprazepam; Deoxydemoxepam; Tranxilium N; Nordazepamum; Nordiazepam; Norprazepam; Nordazepam; Calmday; Vegesan; Nordaz



数据库引用编号

33 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)

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

  • Le-le Wang, Xin-Xin Ren, Yi He, Guan-Feng Cui, Jia-Jia Liu, Juan Jia, Jie Cao, Yao Liu, Bin Cong, Zhi-Wen Wei, Ke-Ming Yun. Pharmacokinetics of Diazepam and Its Metabolites in Urine of Chinese Participants. Drugs in R&D. 2022 Mar; 22(1):43-50. doi: 10.1007/s40268-021-00375-y. [PMID: 35099786]
  • Ina Schenk, Marc Machnik, Diane Broussou, Astrid Meuly, Béatrice B Roques, Elodie Lallemand, Michael Düe, Helma Röttgen, Henrike Lagershausen, Pierre-Louis Toutain, Mario Thevis. Kinetic disposition of diazepam and its metabolites after intravenous administration of diazepam in the horse: Relevance for doping control. Journal of veterinary pharmacology and therapeutics. 2021 Sep; 44(5):733-744. doi: 10.1111/jvp.12991. [PMID: 34115414]
  • Claudia Carelli, Francesca Freni, Matteo Moretti, Claudia Vignali, Marco Ballardini, Luca Morini. A case report on fatal intoxication by tapentadol: Study of distribution and metabolism. Forensic science international. 2021 Jul; 324(?):110825. doi: 10.1016/j.forsciint.2021.110825. [PMID: 34000617]
  • Gamze Avcioglu, Gulsen Yilmaz, Safak Yalcin Sahiner, L Didem Kozaci, Ceylan Bal, Fatma Meric Yilmaz. Evaluation of the diagnostic performance of an oral fluid screening test device for substance abuse at traffic controls. Clinical biochemistry. 2021 Jul; 93(?):112-118. doi: 10.1016/j.clinbiochem.2021.04.009. [PMID: 33882283]
  • 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]
  • Sabrina Lehmann, Alissa Sczyslo, Judith Froch-Cortis, Markus Alexander Rothschild, Mario Thevis, Hilke Andresen-Streichert, Katja Mercer-Chalmers-Bender. Organ distribution of diclazepam, pyrazolam and 3-fluorophenmetrazine. Forensic science international. 2019 Oct; 303(?):109959. doi: 10.1016/j.forsciint.2019.109959. [PMID: 31546164]
  • Michele Fabrazzo, Antonietta Fuschillo, Francesco Perris, Francesco Catapano. The unmasking of hidden severe hyponatremia after long-term combination therapy in exacerbated bipolar patients: a case series. International clinical psychopharmacology. 2019 07; 34(4):206-210. doi: 10.1097/yic.0000000000000265. [PMID: 30998596]
  • 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]
  • 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]
  • Mahsa Torabizadeh, Zahra Talebpour, Nuoshin Adib, Hassan Y Aboul-Enein. Preparation of a novel sorptive stir bar based on vinylpyrrolidone-ethylene glycol dimethacrylate monolithic polymer for the simultaneous extraction of diazepam and nordazepam from human plasma. Journal of separation science. 2016 Apr; 39(7):1316-25. doi: 10.1002/jssc.201501273. [PMID: 26840622]
  • 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]
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  • 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]
  • Alan W Jones, Anita Holmgren. Concentrations of diazepam and nordiazepam in 1,000 blood samples from apprehended drivers--therapeutic use or abuse of anxiolytics?. Journal of pharmacy practice. 2013 Jun; 26(3):198-203. doi: 10.1177/0897190012451910. [PMID: 22797834]
  • Curtis W Probst, William B Thomas, Tamberlyn D Moyers, Tomas Martin, Sherry Cox. Evaluation of plasma diazepam and nordiazepam concentrations following administration of diazepam intravenously or via suppository per rectum in dogs. American journal of veterinary research. 2013 Apr; 74(4):611-5. doi: 10.2460/ajvr.74.4.611. [PMID: 23531069]
  • 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]
  • B KuKanich, J L Nauss. Pharmacokinetics of the cytochrome P-450 substrates phenytoin, theophylline, and diazepam in healthy Greyhound dogs. Journal of veterinary pharmacology and therapeutics. 2012 Jun; 35(3):275-81. doi: 10.1111/j.1365-2885.2011.01316.x. [PMID: 21692812]
  • N Cartiser, F Bévalot, C Le Meur, Y Gaillard, D Malicier, N Hubert, J Guitton. Gas chromatography-tandem mass spectrometry assay for the quantification of four benzodiazepines and citalopram in eleven postmortem rabbit fluids and tissues, with application to animal and human samples. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Oct; 879(27):2909-18. doi: 10.1016/j.jchromb.2011.08.023. [PMID: 21907645]
  • Michael Maringka, Shibashish Giri, Karen Nieber, Ali Acikgöz, Augustinus Bader. Biotransformation of diazepam in a clinically relevant flat membrane bioreactor model using primary porcine hepatocytes. Fundamental & clinical pharmacology. 2011 Jun; 25(3):343-53. doi: 10.1111/j.1472-8206.2010.00857.x. [PMID: 20618872]
  • S E Musulin, C L Mariani, M G Papich. Diazepam pharmacokinetics after nasal drop and atomized nasal administration in dogs. Journal of veterinary pharmacology and therapeutics. 2011 Feb; 34(1):17-24. doi: 10.1111/j.1365-2885.2010.01186.x. [PMID: 21219339]
  • Michael J Lamson, Diane Sitki-Green, Gerald L Wannarka, Michael Mesa, Paul Andrews, John Pellock. Pharmacokinetics of diazepam administered intramuscularly by autoinjector versus rectal gel in healthy subjects: a phase I, randomized, open-label, single-dose, crossover, single-centre study. Clinical drug investigation. 2011; 31(8):585-597. doi: 10.2165/11590250-000000000-00000. [PMID: 21721594]
  • Shanlin Fu, John Lewis, Hongjie Wang, Jim Keegan, Michael Dawson. A novel reductive transformation of oxazepam to nordiazepam observed during enzymatic hydrolysis. Journal of analytical toxicology. 2010 Jun; 34(5):243-51. doi: 10.1093/jat/34.5.243. [PMID: 20529458]
  • Sarah J Glover, Keith R Allen. Measurement of benzodiazepines in urine by liquid chromatography-tandem mass spectrometry: confirmation of samples screened by immunoassay. Annals of clinical biochemistry. 2010 Mar; 47(Pt 2):111-7. doi: 10.1258/acb.2009.009172. [PMID: 19969595]
  • Josh Gunn, Scott Kriger, Andrea R Terrell. Simultaneous determination and quantification of 12 benzodiazepines in serum or whole blood using UPLC/MS/MS. Methods in molecular biology (Clifton, N.J.). 2010; 603(?):107-19. doi: 10.1007/978-1-60761-459-3_10. [PMID: 20077063]
  • Stephanie J Marin, Gwendolyn A McMillin. LC-MS/MS analysis of 13 benzodiazepines and metabolites in urine, serum, plasma, and meconium. Methods in molecular biology (Clifton, N.J.). 2010; 603(?):89-105. doi: 10.1007/978-1-60761-459-3_9. [PMID: 20077062]
  • Bruce A Goldberger, Chris W Chronister, Michele L Merves. Quantitation of benzodiazepines in blood and urine using gas chromatography-mass spectrometry (GC-MS). Methods in molecular biology (Clifton, N.J.). 2010; 603(?):75-87. doi: 10.1007/978-1-60761-459-3_8. [PMID: 20077061]
  • Diogo Oliveira-Silva, Celso H Oliveira, Gustavo D Mendes, Paulo Alexandre R Galvinas, Rafael E Barrientos-Astigarraga, Gilberto De Nucci. Quantification of chlordesmethyldiazepam by liquid chromatography-tandem mass spectrometry: application to a cloxazolam bioequivalence study. Biomedical chromatography : BMC. 2009 Dec; 23(12):1266-75. doi: 10.1002/bmc.1249. [PMID: 19488979]
  • Laura Mercolini, Roberto Mandrioli, Carmelina Iannello, Francesco Matrisciano, Ferdinando Nicoletti, Maria Augusta Raggi. Simultaneous analysis of diazepam and its metabolites in rat plasma and brain tissue by HPLC-UV and SPE. Talanta. 2009 Nov; 80(1):279-85. doi: 10.1016/j.talanta.2009.06.074. [PMID: 19782227]
  • Hironobu Umezawa, Xiao-Pen Lee, Yoshiko Arima, Chika Hasegawa, Akemi Marumo, Takeshi Kumazawa, Keizo Sato. Determination of diazepam and its metabolites in human urine by liquid chromatography/tandem mass spectrometry using a hydrophilic polymer column. Rapid communications in mass spectrometry : RCM. 2008 Aug; 22(15):2333-41. doi: 10.1002/rcm.3613. [PMID: 18618924]
  • Stanislas Grassin Delyle, Charlotte Duverneuil-Mayer, Emuri Abe, Bertille Mathieu, Geoffroy Lorin De La Grandmaison, Philippe Charlier, Jean Claude Alvarez. Fatal intoxication with labetalol (Trandate). Forensic science international. 2008 Jul; 178(2-3):e19-21. doi: 10.1016/j.forsciint.2008.03.003. [PMID: 18406090]
  • R Scott Obach, Franco Lombardo, Nigel J Waters. Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. Drug metabolism and disposition: the biological fate of chemicals. 2008 Jul; 36(7):1385-405. doi: 10.1124/dmd.108.020479. [PMID: 18426954]
  • Pi Cheng, Quan Zhang, Yun-Bao Ma, Zhi-Yong Jiang, Xue-Mei Zhang, Feng-Xue Zhang, Ji-Jun Chen. Synthesis and in vitro anti-hepatitis B virus activities of 4-aryl-6-chloro-quinolin-2-one and 5-aryl-7-chloro-1,4-benzodiazepine derivatives. Bioorganic & medicinal chemistry letters. 2008 Jul; 18(13):3787-9. doi: 10.1016/j.bmcl.2008.05.065. [PMID: 18524583]
  • Craig Lehmann, Gerald L Wannarka. Bioavailability and dose proportionality of intramuscular diazepam administered by autoinjector. Journal of clinical pharmacology. 2008 Apr; 48(4):436-44. doi: 10.1177/0091270007311572. [PMID: 18238878]
  • Guillaume Hoizey, Frédéric Canas, Laurent Binet, Matthieu L Kaltenbach, Gérard Jeunehomme, Marie-Hélène Bernard, Denis Lamiable. Thiodicarb and methomyl tissue distribution in a fatal multiple compounds poisoning. Journal of forensic sciences. 2008 Mar; 53(2):499-502. doi: 10.1111/j.1556-4029.2008.00676.x. [PMID: 18366586]
  • Teijo I Saari, Kari Laine, Leif Bertilsson, Pertti J Neuvonen, Klaus T Olkkola. Voriconazole and fluconazole increase the exposure to oral diazepam. European journal of clinical pharmacology. 2007 Oct; 63(10):941-9. doi: 10.1007/s00228-007-0350-0. [PMID: 17676319]
  • Ilona Fitos, Júlia Visy, Ferenc Zsila, György Mády, Miklós Simonyi. Conformation selectivity in the binding of diazepam and analogues to alpha1-acid glycoprotein. Bioorganic & medicinal chemistry. 2007 Jul; 15(14):4857-62. doi: 10.1016/j.bmc.2007.04.060. [PMID: 17507228]
  • Amir G Kazemifard, Alireza Dabirsiaghi, Kheirollah Gholami, Neda Javadzadeh. New high-performance liquid chromatographic method for serum analysis of oxazepam: application to bioequivalence and pharmacokinetic study. Acta poloniae pharmaceutica. 2007 Jul; 64(4):287-93. doi: NULL. [PMID: 18536153]
  • Marion Pavlic, Kathrin Libiseller, Petra Grubwieser, Heinrich Schubert, Walter Rabl. Medicolegal aspects of tetrazepam metabolism. International journal of legal medicine. 2007 May; 121(3):169-74. doi: 10.1007/s00414-006-0118-6. [PMID: 17021899]
  • Saïd Kinani, Stéphane Bouchonnet, Nathalie Milan, Ivan Ricordel. A sensitive and selective method for the detection of diazepam and its main metabolites in urine by gas chromatography-tandem mass spectrometry. Journal of chromatography. A. 2007 Feb; 1141(1):131-7. doi: 10.1016/j.chroma.2006.12.008. [PMID: 17187809]
  • Lucia Politi, Claudia Vignali, Aldo Polettini. LC-MS-MS analysis of 2,4-dinitrophenol and its phase I and II metabolites in a case of fatal poisoning. Journal of analytical toxicology. 2007 Jan; 31(1):55-61. doi: 10.1093/jat/31.1.55. [PMID: 17389084]
  • Amir G Kazemifard, Kheirollah Gholami, Alireza Dabirsiaghi. Optimized determination of lorazepam in human serum by extraction and high-performance liquid chromatographic analysis. Acta pharmaceutica (Zagreb, Croatia). 2006 Dec; 56(4):481-8. doi: NULL. [PMID: 19839140]
  • Franz E Dussy, Cornelia Hamberg, Thomas A Briellmann. Quantification of benzodiazepines in whole blood and serum. International journal of legal medicine. 2006 Nov; 120(6):323-30. doi: 10.1007/s00414-005-0042-1. [PMID: 16220317]
  • Stephane Pirnay, Françoise Hervé, Stéphane Bouchonnet, Bérengère Perrin, Frédéric J Baud, Ivan Ricordel. Liquid chromatographic-electrospray ionization mass spectrometric quantitative analysis of buprenorphine, norbuprenorphine, nordiazepam and oxazepam in rat plasma. Journal of pharmaceutical and biomedical analysis. 2006 Jun; 41(4):1135-45. doi: 10.1016/j.jpba.2006.02.020. [PMID: 16554136]
  • Florin Marcel Musteata, Mihaela L Musteata, Janusz Pawliszyn. Fast in vivo microextraction: a new tool for clinical analysis. Clinical chemistry. 2006 Apr; 52(4):708-15. doi: 10.1373/clinchem.2005.064758. [PMID: 16497936]
  • Marjorie Chèze, Gaëlle Duffort, Marc Deveaux, Gilbert Pépin. Hair analysis by liquid chromatography-tandem mass spectrometry in toxicological investigation of drug-facilitated crimes: report of 128 cases over the period June 2003-May 2004 in metropolitan Paris. Forensic science international. 2005 Oct; 153(1):3-10. doi: 10.1016/j.forsciint.2005.04.021. [PMID: 15922526]
  • David L Burrows, Andrea Nicolaides, Peter J Rice, Michelle Dufforc, David A Johnson, Kenneth E Ferslew. Papain: a novel urine adulterant. Journal of analytical toxicology. 2005 Jul; 29(5):275-95. doi: 10.1093/jat/29.5.275. [PMID: 16105251]
  • Frank T Peters, Julia Jung, Thomas Kraemer, Hans H Maurer. Fast, simple, and validated gas chromatographic-mass spectrometric assay for quantification of drugs relevant to diagnosis of brain death in human blood plasma samples. Therapeutic drug monitoring. 2005 Jun; 27(3):334-44. doi: 10.1097/01.ftd.0000158079.53577.46. [PMID: 15905804]
  • Paraskevi Valavani, Julia Atta-Politou, Irene Panderi. Development and validation of a liquid chromatographic/electrospray ionization mass spectrometric method for the quantitation of prazepam and its main metabolites in human plasma. Journal of mass spectrometry : JMS. 2005 Apr; 40(4):516-26. doi: 10.1002/jms.824. [PMID: 15712230]
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  • Alan Wayne Jones, Helena Larsson. Distribution of diazepam and nordiazepam between plasma and whole blood and the influence of hematocrit. Therapeutic drug monitoring. 2004 Aug; 26(4):380-5. doi: 10.1097/00007691-200408000-00007. [PMID: 15257067]
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