N-Desmethyltramadol (BioDeep_00000018138)

   

human metabolite Endogenous blood metabolite Chemicals and Drugs


代谢物信息卡片


(1R,2R)-1-(3-methoxyphenyl)-2-[(methylamino)methyl]cyclohexan-1-ol

化学式: C15H23NO2 (249.1728698)
中文名称: (+)-N-去甲基曲马多, 曲马多
谱图信息: 最多检出来源 Mus musculus(urine) 50%

分子结构信息

SMILES: CNCC1CCCCC1(C2=CC(=CC=C2)OC)O
InChI: InChI=1S/C15H23NO2/c1-16-11-13-6-3-4-9-15(13,17)12-7-5-8-14(10-12)18-2/h5,7-8,10,13,16-17H,3-4,6,9,11H2,1-2H3

描述信息

N-Desmethyltramadol is a metabolite of tramadol. Tramadol hydrochloride (trademarked as Conzip, Ryzolt, Ultracet, Ultram in the USA; Ralivia and Zytram XL in Canada) is a centrally-acting synthetic analgesic used to treat moderate to moderately-severe pain. The drug has a wide range of applications, including treatment of rheumatoid arthritis, restless legs syndrome, and fibromyalgia. It was launched and marketed as Tramal by the German pharmaceutical company Grnenthal GmbH in 1977 (Wikipedia).

同义名列表

8 个代谢物同义名

(1R,2R)-1-(3-methoxyphenyl)-2-[(methylamino)methyl]cyclohexan-1-ol; rac N-Desmethyl Tramadol; (+)-N-Desmethyl Tramadol; N-Monodesmethyltramadol; N-Desmethyltramadol; N-Demethyltramadol; Tramadol; M2



数据库引用编号

12 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

1 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)

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PathBank(1)

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

  • Benjamin Kimble, Larry Vogelnest, Peter Valtchev, Merran Govendir. Pharmacokinetic profile of injectable tramadol in the koala (Phascolarctos cinereus) and prediction of its analgesic efficacy. PloS one. 2021; 16(3):e0247546. doi: 10.1371/journal.pone.0247546. [PMID: 33657107]
  • Koji Suzuki, Takafumi Naito, Hironari Tanaka, Yasuhide Yamada, Kunihiko Itoh, Junichi Kawakami. A Reversed-Phase Mode LC-MS/MS Method Using a Polysaccharide Chiral Selector for Simultaneous Quantitation of Each Enantiomer of Tramadol and its Metabolites in Human Plasma and Evaluation of CYP-Mediated Stereoselective Demethylation. Therapeutic drug monitoring. 2020 06; 42(3):503-511. doi: 10.1097/ftd.0000000000000707. [PMID: 31613803]
  • Tania E Perez Jimenez, Butch Kukanich, Hyun Joo, Katrina L Mealey, Tamara L Grubb, Stephen A Greene, Michael H Court. Oral Coadministration of Fluconazole with Tramadol Markedly Increases Plasma and Urine Concentrations of Tramadol and the O-Desmethyltramadol Metabolite in Healthy Dogs. Drug metabolism and disposition: the biological fate of chemicals. 2019 01; 47(1):15-25. doi: 10.1124/dmd.118.083444. [PMID: 30366901]
  • Hironari Tanaka, Takafumi Naito, Hikaru Sato, Takanori Hiraide, Yasuhide Yamada, Junichi Kawakami. Impact of CYP genotype and inflammatory markers on the plasma concentrations of tramadol and its demethylated metabolites and drug tolerability in cancer patients. European journal of clinical pharmacology. 2018 Nov; 74(11):1461-1469. doi: 10.1007/s00228-018-2527-0. [PMID: 30051214]
  • P Cagnardi, C Ferraresi, A Zonca, A Pecile, G Ravasio, D D Zani, R Villa. Clinical pharmacokinetics of tramadol and main metabolites in horses undergoing orchiectomy. The veterinary quarterly. 2014; 34(3):143-51. doi: 10.1080/01652176.2014.963208. [PMID: 25211185]
  • Nunziata Barbera, Marco Fisichella, Andrea Bosco, Francesca Indorato, Giorgio Spadaro, Guido Romano. A suicidal poisoning due to tramadol. A metabolic approach to death investigation. Journal of forensic and legal medicine. 2013 Jul; 20(5):555-8. doi: 10.1016/j.jflm.2013.03.006. [PMID: 23756535]
  • Abdel-Aziz Y El-Sayed, Khaled M Mohamed, Ahmed Y Nasser, Jennifer Button, David W Holt. Simultaneous determination of tramadol, O-desmethyltramadol and N-desmethyltramadol in human urine by gas chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 May; 926(?):9-15. doi: 10.1016/j.jchromb.2013.02.019. [PMID: 23542669]
  • Janet K Coller, Jennifer R Michalakas, Heather M James, Aaron L Farquharson, Joel Colvill, Jason M White, Andrew A Somogyi. Inhibition of CYP2D6-mediated tramadol O-demethylation in methadone but not buprenorphine maintenance patients. British journal of clinical pharmacology. 2012 Nov; 74(5):835-41. doi: 10.1111/j.1365-2125.2012.04256.x. [PMID: 22369095]
  • Binh T Ly, Stephen L Thornton, Colleen Buono, Judith A Stone, Alan H B Wu. False-positive urine phencyclidine immunoassay screen result caused by interference by tramadol and its metabolites. Annals of emergency medicine. 2012 Jun; 59(6):545-7. doi: 10.1016/j.annemergmed.2011.08.013. [PMID: 21924518]
  • Natália Valadares de Moraes, Gabriela Rocha Lauretti, Marcio Nogueira Napolitano, Naiane Ribeiro Santos, Ana Leonor Pardo Campos Godoy, Vera Lucia Lanchote. Enantioselective analysis of unbound tramadol, O-desmethyltramadol and N-desmethyltramadol in plasma by ultrafiltration and LC-MS/MS: application to clinical pharmacokinetics. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Jan; 880(1):140-7. doi: 10.1016/j.jchromb.2011.11.033. [PMID: 22173007]
  • M V Tzvetkov, A R Saadatmand, J Lötsch, I Tegeder, J C Stingl, J Brockmöller. Genetically polymorphic OCT1: another piece in the puzzle of the variable pharmacokinetics and pharmacodynamics of the opioidergic drug tramadol. Clinical pharmacology and therapeutics. 2011 Jul; 90(1):143-50. doi: 10.1038/clpt.2011.56. [PMID: 21562485]
  • Allison J Stewart, Dawn M Boothe, Crisanta Cruz-Espindola, Emily J Mitchum, Jenny Springfield. Pharmacokinetics of tramadol and metabolites O-desmethyltramadol and N-desmethyltramadol in adult horses. American journal of veterinary research. 2011 Jul; 72(7):967-74. doi: 10.2460/ajvr.72.7.967. [PMID: 21728858]
  • Ana Leonor Pardo Campos Godoy, Natália Valadares De Moraes, Edson Zangiacomi Martinez, Teresa Maria De Jesus Ponte Carvalho, Maria Paula Marques, Vera Lucia Lanchote. Simultaneous analysis of tramadol, O-desmethyltramadol, and N-desmethyltramadol enantiomers in rat plasma by high-performance liquid chromatography-tandem mass spectrometry: application to pharmacokinetics. Chirality. 2011 Apr; 23(4):287-93. doi: 10.1002/chir.20914. [PMID: 21384434]
  • B De Backer, F Renardy, R Denooz, C Charlier. Quantification in postmortem blood and identification in urine of tramadol and its two main metabolites in two cases of lethal tramadol intoxication. Journal of analytical toxicology. 2010 Nov; 34(9):599-604. doi: 10.1093/jat/34.9.599. [PMID: 21073815]
  • Mario Giorgi, Giuseppe Saccomanni, Beata Lebkowska-Wieruszewska, Cezary Kowalski. Pharmacokinetic evaluation of tramadol and its major metabolites after single oral sustained tablet administration in the dog: a pilot study. Veterinary journal (London, England : 1997). 2009 May; 180(2):253-5. doi: 10.1016/j.tvjl.2007.12.011. [PMID: 18313955]
  • Yalda H Ardakani, Reza Mehvar, Alireza Foroumadi, Mohammad-Reza Rouini. Enantioselective determination of tramadol and its main phase I metabolites in human plasma by high-performance liquid chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2008 Mar; 864(1-2):109-15. doi: 10.1016/j.jchromb.2008.01.038. [PMID: 18282749]
  • Suvi Ojanperä, Ilpo Rasanen, Johanna Sistonen, Anna Pelander, Erkki Vuori, Ilkka Ojanperä. Quantification of drugs in plasma without primary reference standards by liquid chromatography-chemiluminescence nitrogen detection: application to tramadol metabolite ratios. Therapeutic drug monitoring. 2007 Aug; 29(4):423-8. doi: 10.1097/ftd.0b013e318074de97. [PMID: 17667796]
  • K Allegaert, R Verbesselt, M Rayyan, A Debeer, J de Hoon. Urinary metabolites to assess in vivo ontogeny of hepatic drug metabolism in early neonatal life. Methods and findings in experimental and clinical pharmacology. 2007 May; 29(4):251-6. doi: 10.1358/mf.2007.29.4.1106408. [PMID: 17609736]
  • Emilio García Quetglas, Jose Ramón Azanza, Ernesto Cardenas, Belén Sádaba, Miguel Angel Campanero. Stereoselective pharmacokinetic analysis of tramadol and its main phase I metabolites in healthy subjects after intravenous and oral administration of racemic tramadol. Biopharmaceutics & drug disposition. 2007 Jan; 28(1):19-33. doi: 10.1002/bdd.526. [PMID: 17061296]
  • K Allegaert, J N Van den Anker, A Debeer, V Cossey, R Verbesselt, D Tibboel, H Devlieger, J de Hoon. Maturational changes in the in vivo activity of CYP3A4 in the first months of life. International journal of clinical pharmacology and therapeutics. 2006 Jul; 44(7):303-8. doi: 10.5414/cpp44303. [PMID: 16961158]
  • B Elsing, G Blaschke. Achiral and chiral high-performance liquid chromatographic determination of tramadol and its major metabolites in urine after oral administration of racemic tramadol. Journal of chromatography. 1993 Feb; 612(2):223-30. doi: 10.1016/0378-4347(93)80167-3. [PMID: 8468380]