Morphine-6-glucuronide (BioDeep_00001871391)

Main id: BioDeep_00000002925

 

natural product


代谢物信息卡片


M-6-G TRIFLUOROACETATE-HYDRATE

化学式: C23H27NO9 (461.1685732000001)
中文名称: 甲醇:水(1:1)测试标样(吗啡-6-Β-D-葡糖苷酸)
谱图信息: 最多检出来源 Homo sapiens(blood) 87.5%

分子结构信息

SMILES: CN1CCC23C4C1CC5=C2C(=C(C=C5)O)OC3C(C=C4)OC6C(C(C(C(O6)C(=O)O)O)O)O
InChI: InChI=1S/C23H27NO9/c1-24-7-6-23-10-3-5-13(31-22-17(28)15(26)16(27)19(33-22)21(29)30)20(23)32-18-12(25)4-2-9(14(18)23)8-11(10)24/h2-5,10-11,13,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30)/t10-,11+,13-,15-,16-,17+,19-,20-,22+,23-/m0/s1

描述信息

D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids
C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist > C1657 - Opiate

同义名列表

3 个代谢物同义名

M-6-G TRIFLUOROACETATE-HYDRATE; Morphine-6-glucuronide; Morphine-6-glucuronide



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

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)

8 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

  • Briana D Hamamoto-Hardman, Eugene P Steffey, Kelsey Seminoff, Daniel S McKemie, Philip Kass, Heather K Knych. Preliminary study of the pharmacokinetics, tissue distribution, and behavioral and select physiological effects of morphine 6-glucuronide (M6G) following intravenous administration to horses. Canadian journal of veterinary research = Revue canadienne de recherche veterinaire. 2022 Jul; 86(3):172-180. doi: . [PMID: 35794968]
  • Thomas Duflot, Tony Pereira, Marie-Pierre Tavolacci, Robinson Joannidès, Frédéric Aubrun, Fabien Lamoureux, Virginie Eve Lvovschi. Pharmacokinetic modeling of morphine and its glucuronides: Comparison of nebulization versus intravenous route in healthy volunteers. CPT: pharmacometrics & systems pharmacology. 2022 01; 11(1):82-93. doi: 10.1002/psp4.12735. [PMID: 34842366]
  • Laurens F M Verscheijden, Carlijn H C Litjens, Jan B Koenderink, Ron H J Mathijssen, Marcel M Verbeek, Saskia N de Wildt, Frans G M Russel. Physiologically based pharmacokinetic/pharmacodynamic model for the prediction of morphine brain disposition and analgesia in adults and children. PLoS computational biology. 2021 03; 17(3):e1008786. doi: 10.1371/journal.pcbi.1008786. [PMID: 33661919]
  • Harald Ihmsen, Jürgen Schüttler, Christian Jeleazcov. Pharmacokinetics of Morphine and Morphine-6-Glucuronide During Postoperative Pain Therapy in Cardiac Surgery Patients. European journal of drug metabolism and pharmacokinetics. 2021 Mar; 46(2):249-263. doi: 10.1007/s13318-020-00663-z. [PMID: 33547559]
  • S R Gretler, C J Finno, P H Kass, H K Knych. Functional phenotyping of the CYP2D6 probe drug codeine in the horse. BMC veterinary research. 2021 Feb; 17(1):77. doi: 10.1186/s12917-021-02788-y. [PMID: 33581736]
  • Alessandro Mirra, Jasmin Birras, Sabina Diez Bernal, Claudia Spadavecchia. Morphine plasmatic concentration in a pregnant mare and its foal after long term epidural administration. BMC veterinary research. 2020 Jan; 16(1):19. doi: 10.1186/s12917-020-2242-9. [PMID: 31959188]
  • Luying Wang, Chunfang Ni, Hongliang Shen, Zhenhai Sheng, Chen Liang, Rong Wang, Yurong Zhang. Comparison of the Detection Windows of Heroin Metabolites in Human Urine Using Online SPE and LC-MS/MS: Importance of Morphine-3-Glucuronide. Journal of analytical toxicology. 2020 Jan; 44(1):22-28. doi: 10.1093/jat/bkz040. [PMID: 31095707]
  • S Merchaoui, A Ben Said, K Louati, A Hajri, F Safta, M Kallel. Optimization of morphine extraction method for the assay of its urinary 3-glucuronideconjuguate by gas chromatography-mass spectrometry. Annales pharmaceutiques francaises. 2019 Nov; 77(6):468-487. doi: 10.1016/j.pharma.2019.07.004. [PMID: 31564417]
  • Eric R Kinzler, Carmela Pantaleon, Matthew Iverson, Stefan Aigner. A Randomized, Crossover Study on the Effect of Food on the Pharmacokinetic Characteristics of Morphine ARER (MorphaBond™ ER), an Abuse-Deterrent Formulation of Extended-Release Morphine. Advances in therapy. 2019 09; 36(9):2394-2401. doi: 10.1007/s12325-019-01022-4. [PMID: 31278694]
  • Briana D Hamamoto-Hardman, Eugene P Steffey, Daniel Weiner, Daniel S McKemie, Philip Kass, Heather K Knych. Pharmacokinetics and selected pharmacodynamics of morphine and its active metabolites in horses after intravenous administration of four doses. Journal of veterinary pharmacology and therapeutics. 2019 Jul; 42(4):401-410. doi: 10.1111/jvp.12759. [PMID: 30919469]
  • Cecilie Hasselø Thaulow, Åse Marit Leere Øiestad, Sidsel Rogde, Jannike Mørch Andersen, Gudrun Høiseth, Marte Handal, Jørg Mørland, Vigdis Vindenes. Can measurements of heroin metabolites in post-mortem matrices other than peripheral blood indicate if death was rapid or delayed?. Forensic science international. 2018 Sep; 290(?):121-128. doi: 10.1016/j.forsciint.2018.06.041. [PMID: 30015276]
  • Eric R Kinzler, Carmela Pantaleon, Stefan Aigner. Relative Oral Bioavailability of an Abuse-deterrent, Extended-release Formulation of Morphine Versus Extended-release Morphine: A 2-period, Single-dose, Randomized Crossover Study in Healthy Subjects. Clinical therapeutics. 2018 08; 40(8):1357-1365. doi: 10.1016/j.clinthera.2018.06.010. [PMID: 30049503]
  • H H Doyle, A Z Murphy. Sex-dependent influences of morphine and its metabolites on pain sensitivity in the rat. Physiology & behavior. 2018 04; 187(?):32-41. doi: 10.1016/j.physbeh.2017.11.030. [PMID: 29199028]
  • Lorry Hachon, Rafael Reis, Laurence Labat, Christine Poitou, Aude Jacob, Xavier Declèves, Celia Lloret-Linares. Morphine and metabolites plasma levels after administration of sustained release morphine in Roux-en-Y gastric bypass subjects versus matched control subjects. Surgery for obesity and related diseases : official journal of the American Society for Bariatric Surgery. 2017 Nov; 13(11):1869-1874. doi: 10.1016/j.soard.2017.07.030. [PMID: 28864105]
  • Yan Wang, Kerry B Goralski, Derek J Roberts, Kathryn Landry, Mark E Issa, Lekha Sleno, Lisa C Julien, Jeremy Wood, Richard I Hall. An observational study examining the effects of a surgically induced inflammatory response on the distribution of morphine and its metabolites into cerebrospinal fluid. Canadian journal of anaesthesia = Journal canadien d'anesthesie. 2017 Oct; 64(10):1009-1022. doi: 10.1007/s12630-017-0933-x. [PMID: 28710563]
  • Astrid W Oosten, João A Abrantes, Siv Jönsson, Maja Matic, Ron H N van Schaik, Peter de Bruijn, Carin C D van der Rijt, Ron H J Mathijssen. A Prospective Population Pharmacokinetic Study on Morphine Metabolism in Cancer Patients. Clinical pharmacokinetics. 2017 07; 56(7):733-746. doi: 10.1007/s40262-016-0471-7. [PMID: 27815868]
  • Pongkwan Sitasuwan, Cathleen Melendez, Margarita Marinova, Kaylee R Mastrianni, Alicia Darragh, Emily Ryan, L Andrew Lee. Degradation of Opioids and Opiates During Acid Hydrolysis Leads to Reduced Recovery Compared to Enzymatic Hydrolysis. Journal of analytical toxicology. 2016 Oct; 40(8):601-607. doi: 10.1093/jat/bkw085. [PMID: 27702939]
  • David Sartori, Tamorah Lewis, Autumn Breaud, William Clarke. The development of a high-performance liquid chromatography-tandem mass spectrometric method for simultaneous quantification of morphine, morphine-3-β-glucuronide, morphine-6-β-glucuronide, hydromorphone, and normorphine in serum. Clinical biochemistry. 2015 Dec; 48(18):1283-90. doi: 10.1016/j.clinbiochem.2015.05.023. [PMID: 26118474]
  • Yong Joo Lee, Sang-Yeon Suh, Junghan Song, Sanghee Shiny Lee, Ah-Ram Seo, Hong-Yup Ahn, Myung Ah Lee, Chul-Min Kim, Pål Klepstad. Serum and urine concentrations of morphine and morphine metabolites in patients with advanced cancer receiving continuous intravenous morphine: an observational study. BMC palliative care. 2015 Oct; 14(?):53. doi: 10.1186/s12904-015-0052-9. [PMID: 26507979]
  • Nieves Velez de Mendizabal, Ricardo Jimenez-Mendez, Erin Cooke, Carolyne J Montgomery, Joy Dawes, Michael J Rieder, Katarina Aleksa, Gideon Koren, Carlos O Jacobo-Cabral, Rodrigo Gonzalez-Ramirez, Gilberto Castañeda-Hernandez, Bruce C Carleton. A Compartmental Analysis for Morphine and Its Metabolites in Young Children After a Single Oral Dose. Clinical pharmacokinetics. 2015 Oct; 54(10):1083-90. doi: 10.1007/s40262-015-0256-4. [PMID: 25773480]
  • B C Ferslew, C K Johnston, E Tsakalozou, A S Bridges, M F Paine, W Jia, P W Stewart, A S Barritt, K L R Brouwer. Altered morphine glucuronide and bile acid disposition in patients with nonalcoholic steatohepatitis. Clinical pharmacology and therapeutics. 2015 Apr; 97(4):419-27. doi: 10.1002/cpt.66. [PMID: 25669174]
  • Anika L Dzierlenga, John D Clarke, Tiffanie L Hargraves, Garrett R Ainslie, Todd W Vanderah, Mary F Paine, Nathan J Cherrington. Mechanistic basis of altered morphine disposition in nonalcoholic steatohepatitis. The Journal of pharmacology and experimental therapeutics. 2015 Mar; 352(3):462-70. doi: 10.1124/jpet.114.220764. [PMID: 25512370]
  • Oscar A Linares, Jeffrey Fudin, William E Schiesser, Annemarie L Daly Linares, Raymond C Boston. CYP2D6 phenotype-specific codeine population pharmacokinetics. Journal of pain & palliative care pharmacotherapy. 2015 Mar; 29(1):4-15. doi: 10.3109/15360288.2014.997854. [PMID: 25562725]
  • Anne Brokjær, Mads Kreilgaard, Anne Estrup Olesen, Ulrika S H Simonsson, Lona Louring Christrup, Albert Dahan, Asbjørn Mohr Drewes. Population pharmacokinetics of morphine and morphine-6-glucuronide following rectal administration--a dose escalation study. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2015 Feb; 68(?):78-86. doi: 10.1016/j.ejps.2014.12.004. [PMID: 25486331]
  • Theresa A Isbell, Erin C Strickland, Jennifer Hitchcock, Gregory McIntire, Christa L Colyer. Capillary electrophoresis-mass spectrometry determination of morphine and its isobaric glucuronide metabolites. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2015 Feb; 980(?):65-71. doi: 10.1016/j.jchromb.2014.11.035. [PMID: 25589256]
  • R Klimas, G Mikus. Morphine-6-glucuronide is responsible for the analgesic effect after morphine administration: a quantitative review of morphine, morphine-6-glucuronide, and morphine-3-glucuronide. British journal of anaesthesia. 2014 Dec; 113(6):935-44. doi: 10.1093/bja/aeu186. [PMID: 24985077]
  • C H Thaulow, G Høiseth, J M Andersen, M Handal, J Mørland. Pharmacokinetic interactions between ethanol and heroin: a study on post-mortem cases. Forensic science international. 2014 Sep; 242(?):127-134. doi: 10.1016/j.forsciint.2014.06.032. [PMID: 25050840]
  • Ana Oliveira, Félix Carvalho, Paula Guedes Pinho, Fernando Remião, Rui Medeiros, Ricardo Jorge Dinis-Oliveira. Quantification of morphine and its major metabolites M3G and M6G in antemortem and postmortem samples. Biomedical chromatography : BMC. 2014 Sep; 28(9):1263-70. doi: 10.1002/bmc.3158. [PMID: 25237710]
  • H K Knych, E P Steffey, D S McKemie. Preliminary pharmacokinetics of morphine and its major metabolites following intravenous administration of four doses to horses. Journal of veterinary pharmacology and therapeutics. 2014 Aug; 37(4):374-81. doi: 10.1111/jvp.12098. [PMID: 24479785]
  • Ana Oliveira, Dora Pinho, António Albino-Teixeira, Rui Medeiros, Ricardo Jorge Dinis-Oliveira, Félix Carvalho. Morphine glucuronidation increases its analgesic effect in guinea pigs. Life sciences. 2014 Jul; 109(2):104-10. doi: 10.1016/j.lfs.2014.06.010. [PMID: 24968302]
  • Simona De Gregori, Cristina E Minella, Manuela De Gregori, Carmine Tinelli, Guglielmina N Ranzani, Stefano Govoni, Massimo Allegri, Mario Regazzi. Clinical pharmacokinetics of morphine and its metabolites during morphine dose titration for chronic cancer pain. Therapeutic drug monitoring. 2014 Jun; 36(3):335-44. doi: 10.1097/ftd.0000000000000009. [PMID: 24595069]
  • Nuy Chau, David J Elliot, Benjamin C Lewis, Kushari Burns, Martin R Johnston, Peter I Mackenzie, John O Miners. Morphine glucuronidation and glucosidation represent complementary metabolic pathways that are both catalyzed by UDP-glucuronosyltransferase 2B7: kinetic, inhibition, and molecular modeling studies. The Journal of pharmacology and experimental therapeutics. 2014 Apr; 349(1):126-37. doi: 10.1124/jpet.113.212258. [PMID: 24459244]
  • Susan Luong, Shanlin Fu. Detection and identification of 2-nitro-morphine and 2-nitro-morphine-6-glucuronide in nitrite adulterated urine specimens containing morphine and its glucuronides. Drug testing and analysis. 2014 Mar; 6(3):277-87. doi: 10.1002/dta.1476. [PMID: 23592389]
  • Maja Matic, Elisabeth Norman, Anders Rane, Olof Beck, Maria Andersson, Laure Elens, Dick Tibboel, Vineta Fellman, Ron H N van Schaik. Effect of UGT2B7 -900G>A (-842G>A; rs7438135) on morphine glucuronidation in preterm newborns: results from a pilot cohort. Pharmacogenomics. 2014; 15(12):1589-97. doi: 10.2217/pgs.14.115. [PMID: 25340733]
  • Xiujun Wu, Li Yuan, Jinliang Zuo, Jing Lv, Tao Guo. The impact of CYP2D6 polymorphisms on the pharmacokinetics of codeine and its metabolites in Mongolian Chinese subjects. European journal of clinical pharmacology. 2014 Jan; 70(1):57-63. doi: 10.1007/s00228-013-1573-x. [PMID: 24077935]
  • Alexis Laux-Biehlmann, Hélène Chung, Jinane Mouheiche, Julie Vérièpe, François Delalande, Marc Lamshöft, Ingeborg D Welters, Stéphanie Soldevila, Hervé Bazin, Laurent Lamarque, Alain Van Dorsselaer, Pierrick Poisbeau, Francis Schneider, Yannick Goumon, Patrick Garnero. Endogenous morphine-6-glucuronide (M6G) is present in the plasma of patients: validation of a specific anti-M6G antibody for clinical and basic research. BioFactors (Oxford, England). 2014 Jan; 40(1):113-20. doi: 10.1002/biof.1107. [PMID: 23861301]
  • Catherine Dicaire, Jean-Nicholas Mess, Milton Furtado, Annik Bergeron, Fabio Garofolo. Impact of organic solvent additive on the integrity of plasma samples in bioanalysis by LC-MS/MS. Bioanalysis. 2013 Oct; 5(19):2359-70. doi: 10.4155/bio.13.207. [PMID: 24066621]
  • Nuggehally R Srinivas. Do we have clarity on the therapeutic levels of morphine and its metabolites: seeking answers for the dilemma?. Journal of pain & palliative care pharmacotherapy. 2013 Jun; 27(2):163-6. doi: 10.3109/15360288.2013.788597. [PMID: 23789848]
  • N Dubols, C Hallet, D Luppens, M Ansseau, C Charlier. [Rapid opiate detoxification under anesthesia (RODA)]. Revue medicale de Liege. 2013 May; 68(5-6):298-302. doi: NULL. [PMID: 23888580]
  • Lin Yang, J Paul Fawcett, Hu Zhang, Ian G Tucker. Effect of 12-oxochenodeoxycholate on the pharmacokinetics and pharmacodynamics of morphine 6-glucuronide in Wistar rats. The Journal of pharmacy and pharmacology. 2013 Apr; 65(4):561-6. doi: 10.1111/jphp.12020. [PMID: 23488785]
  • Naoki Inui, Tatsuhisa Kato, Shinya Uchida, Kingo Chida, Kazuhiko Takeuchi, Takahito Kimura, Hiroshi Watanabe. Novel patch for transdermal administration of morphine. Journal of pain and symptom management. 2012 Oct; 44(4):479-85. doi: 10.1016/j.jpainsymman.2011.10.022. [PMID: 22727949]
  • Jane A Dickerson, Thomas J Laha, Monica B Pagano, Brendan R O'Donnell, Andrew N Hoofnagle. Improved detection of opioid use in chronic pain patients through monitoring of opioid glucuronides in urine. Journal of analytical toxicology. 2012 Oct; 36(8):541-7. doi: 10.1093/jat/bks063. [PMID: 22833646]
  • J A Hannam, B J Anderson. Contribution of morphine and morphine-6-glucuronide to respiratory depression in a child. Anaesthesia and intensive care. 2012 Sep; 40(5):867-70. doi: 10.1177/0310057x1204000516. [PMID: 22934872]
  • Kristin Moksnes, Stein Kaasa, Ørnulf Paulsen, Jan Henrik Rosland, Olav Spigset, Ola Dale. Serum concentrations of opioids when comparing two switching strategies to methadone for cancer pain. European journal of clinical pharmacology. 2012 Aug; 68(8):1147-56. doi: 10.1007/s00228-012-1228-3. [PMID: 22374345]
  • Heungyeung Yau, Allison Dominowski, Christy Schaible, Gerald Siefring, Nihmat Morjana. Performance of the Emit® II Plus 6-Acetylmorphine Assay on the Viva-E® analyzer. Forensic science international. 2012 Jul; 220(1-3):97-102. doi: 10.1016/j.forsciint.2012.02.004. [PMID: 22410425]
  • Juliana P Figueiredo, William W Muir, Richard Sams. Cardiorespiratory, gastrointestinal, and analgesic effects of morphine sulfate in conscious healthy horses. American journal of veterinary research. 2012 Jun; 73(6):799-808. doi: 10.2460/ajvr.73.6.799. [PMID: 22620693]
  • Maria Meringolo, Valentina Brusadin, Maria T De Luca, Christian Montanari, Christian L Montanari, Letizia Antonilli, Paolo Nencini, Aldo Badiani. Induction of morphine-6-glucuronide synthesis by heroin self-administration in the rat. Psychopharmacology. 2012 May; 221(2):195-203. doi: 10.1007/s00213-011-2534-7. [PMID: 22016196]
  • Eloise A Gelston, Janet K Coller, Olga V Lopatko, Heather M James, Helmut Schmidt, Jason M White, Andrew A Somogyi. Methadone inhibits CYP2D6 and UGT2B7/2B4 in vivo: a study using codeine in methadone- and buprenorphine-maintained subjects. British journal of clinical pharmacology. 2012 May; 73(5):786-94. doi: 10.1111/j.1365-2125.2011.04145.x. [PMID: 22092298]
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  • Thomas Eissing, Jörg Lippert, Stefan Willmann. Pharmacogenomics of codeine, morphine, and morphine-6-glucuronide: model-based analysis of the influence of CYP2D6 activity, UGT2B7 activity, renal impairment, and CYP3A4 inhibition. Molecular diagnosis & therapy. 2012 Feb; 16(1):43-53. doi: 10.2165/11597930-000000000-00000. [PMID: 22352453]
  • Hahck Soo Park, Jong Hak Kim, Yi Jeong Kim, Dong Yeon Kim. Plasma Concentrations of Morphine during Postoperative Pain Control. The Korean journal of pain. 2011 Sep; 24(3):146-53. doi: 10.3344/kjp.2011.24.3.146. [PMID: 21935493]
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  • Chang-Shu Zhan, Bao-Hua Shen, Xian-Yi Zhuo. [Simultaneous determination of opioid compounds in human urine by UPLC-MS/MS]. Fa yi xue za zhi. 2010 Jun; 26(3):188-91. doi: NULL. [PMID: 20707277]
  • Kirsten Abildskov, Piper Weldy, Marianne Garland. Molecular cloning of the baboon UDP-glucuronosyltransferase 2B gene family and their activity in conjugating morphine. Drug metabolism and disposition: the biological fate of chemicals. 2010 Apr; 38(4):545-53. doi: 10.1124/dmd.109.030635. [PMID: 20071451]
  • Shawn McCann, Tony L Yaksh, Charles F von Gunten. Correlation between myoclonus and the 3-glucuronide metabolites in patients treated with morphine or hydromorphone: a pilot study. Journal of opioid management. 2010 Mar; 6(2):87-94. doi: 10.5055/jom.2010.0008. [PMID: 20481173]
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