Morphine-6-glucuronide (BioDeep_00000002925)

 

Secondary id: BioDeep_00001871391

human metabolite Endogenous blood metabolite


代谢物信息卡片


(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-yl]oxy}oxane-2-carboxylic acid

化学式: C23H27NO9 (461.1685732000001)
中文名称: 吗啡-6-Β-D-葡糖苷酸
谱图信息: 最多检出来源 Homo sapiens(blood) 0.44%

Reviewed

Last reviewed on 2024-08-14.

Cite this Page

Morphine-6-glucuronide. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/morphine-6-glucuronide (retrieved 2024-09-17) (BioDeep RN: BioDeep_00000002925). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

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

Morphine-6-glucuronide (M6G) is a major active metabolite of morphine, and as such is the molecule responsible for much of the pain-relieving effects of morphine (and thus heroin). M6G is formed from morphine by the enzyme UDP-Glucuronosyltransferase-2B7 (UGT2B7). M6G can accumulate to toxic levels in kidney failure.
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

6 个代谢物同义名

(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10,15-tetraen-14-yl]oxy}oxane-2-carboxylic acid; M-6-G TRIFLUOROACETATE-HYDRATE; Morphine 6-glucuronide(minor); Morphine-6beta-glucuronide; Morphine 6-glucuronide; Morphine-6-glucuronide



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)

BioCyc(0)

PlantCyc(0)

代谢反应

4 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(1)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(2)

PharmGKB(1)

3 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]
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  • 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]
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  • 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]
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  • 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]
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