Codeine-6-glucuronide (BioDeep_00000011280)

 

Secondary id: BioDeep_00001868992

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-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18),15-tetraen-14-yl]oxy}oxane-2-carboxylic acid

化学式: C24H29NO9 (475.18422240000007)
中文名称:
谱图信息: 最多检出来源 Viridiplantae(plant) 0.18%

分子结构信息

SMILES: CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)OC6C(C(C(C(O6)C(=O)O)O)O)O
InChI: InChI=1S/C24H29NO9/c1-25-8-7-24-11-4-6-14(32-23-18(28)16(26)17(27)20(34-23)22(29)30)21(24)33-19-13(31-2)5-3-10(15(19)24)9-12(11)25/h3-6,11-12,14,16-18,20-21,23,26-28H,7-9H2,1-2H3,(H,29,30)/t11-,12+,14-,16-,17-,18+,20-,21-,23+,24-/m0/s1

描述信息

Codeine-6-glucuronide (C6G) is a major active metabolite of codeine and may be responsible for as much as 60\\% of the analgesic effects of codeine. C6G exhibits decreased immunosuppressive effects compared to codeine. During its metabolism, codeine is conjugated with glucuronic acid by the enzyme UDP-Glucuronosyltransferase-2B7 (UGT2B7) to form codeine-6-glucuronide. (Wikipedia)
D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids

同义名列表

2 个代谢物同义名

(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18),15-tetraen-14-yl]oxy}oxane-2-carboxylic acid; Codeine-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

3 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(2)

PharmGKB(1)

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

  • Yao-Te Yen, Yin-Jue Chang, Pin-Jung Lai, Chi-Lun Chang, Ting-Yueh Chen, San-Chong Chyueh. A Study of Opiate, Opiate Metabolites and Antihistamines in Urine after Consumption of Cold Syrups by LC-MS/MS. Molecules (Basel, Switzerland). 2020 Feb; 25(4):. doi: 10.3390/molecules25040972. [PMID: 32098143]
  • B KuKanich. Pharmacokinetics and pharmacodynamics of oral acetaminophen in combination with codeine in healthy Greyhound dogs. Journal of veterinary pharmacology and therapeutics. 2016 Oct; 39(5):514-7. doi: 10.1111/jvp.12299. [PMID: 26896302]
  • 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]
  • 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]
  • 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]
  • Pritsana Raungrut, Verawan Uchaipichat, David J Elliot, Benjamas Janchawee, Andrew A Somogyi, John O Miners. In vitro-in vivo extrapolation predicts drug-drug interactions arising from inhibition of codeine glucuronidation by dextropropoxyphene, fluconazole, ketoconazole, and methadone in humans. The Journal of pharmacology and experimental therapeutics. 2010 Aug; 334(2):609-18. doi: 10.1124/jpet.110.167916. [PMID: 20484152]
  • Hadi Molanaei, Juan Jesus Carrero, Olof Heimbürger, Louise Nordfors, Bengt Lindholm, Peter Stenvinkel, Ingegerd Odar-Cederlöf, Leif Bertilsson. Influence of the CYP2D6 polymorphism and hemodialysis on codeine disposition in patients with end-stage renal disease. European journal of clinical pharmacology. 2010 Mar; 66(3):269-73. doi: 10.1007/s00228-009-0759-8. [PMID: 19940985]
  • J Kirchheiner, H Schmidt, M Tzvetkov, J-T H A Keulen, J Lötsch, I Roots, J Brockmöller. Pharmacokinetics of codeine and its metabolite morphine in ultra-rapid metabolizers due to CYP2D6 duplication. The pharmacogenomics journal. 2007 Aug; 7(4):257-65. doi: 10.1038/sj.tpj.6500406. [PMID: 16819548]
  • Jens Trafkowski, Burkhard Madea, Frank Musshoff. The significance of putative urinary markers of illicit heroin use after consumption of poppy seed products. Therapeutic drug monitoring. 2006 Aug; 28(4):552-8. doi: 10.1097/00007691-200608000-00011. [PMID: 16885724]
  • Jörn Lötsch, Carsten Skarke, Helmut Schmidt, Maren Rohrbacher, Ute Hofmann, Matthias Schwab, Gerd Geisslinger. Evidence for morphine-independent central nervous opioid effects after administration of codeine: contribution of other codeine metabolites. Clinical pharmacology and therapeutics. 2006 Jan; 79(1):35-48. doi: 10.1016/j.clpt.2005.09.005. [PMID: 16413240]
  • Constance M Murphy, Marilyn A Huestis. LC-ESI-MS/MS analysis for the quantification of morphine, codeine, morphine-3-beta-D-glucuronide, morphine-6-beta-D-glucuronide, and codeine-6-beta-D-glucuronide in human urine. Journal of mass spectrometry : JMS. 2005 Nov; 40(11):1412-6. doi: 10.1002/jms.921. [PMID: 16258895]
  • Susanne Ammon, Claudia Marx, Christoph Behrens, Ute Hofmann, Thomas Mürdter, Ernst-Ulrich Griese, Gerd Mikus. Diclofenac does not interact with codeine metabolism in vivo: a study in healthy volunteers. BMC clinical pharmacology. 2002 Feb; 2(?):2. doi: 10.1186/1472-6904-2-2. [PMID: 11943073]
  • M J Bogusz, R D Maier, M Erkens, U Kohls. Detection of non-prescription heroin markers in urine with liquid chromatography-atmospheric pressure chemical ionization mass spectrometry. Journal of analytical toxicology. 2001 Sep; 25(6):431-8. doi: 10.1093/jat/25.6.431. [PMID: 11550816]
  • S Ammon, O von Richter, U Hofmann, K P Thon, M Eichelbaum, G Mikus. In vitro interaction of codeine and diclofenac. Drug metabolism and disposition: the biological fate of chemicals. 2000 Oct; 28(10):1149-52. doi: . [PMID: 10997932]
  • M J Bogusz, R D Maier, M Erkens, S Driessen. Determination of morphine and its 3- and 6-glucuronides, codeine, codeine-glucuronide and 6-monoacetylmorphine in body fluids by liquid chromatography atmospheric pressure chemical ionization mass spectrometry. Journal of chromatography. B, Biomedical sciences and applications. 1997 Dec; 703(1-2):115-27. doi: 10.1016/s0378-4347(97)00384-8. [PMID: 9448068]
  • P Lafolie, O Beck, Z Lin, F Albertioni, L Boréus. Urine and plasma pharmacokinetics of codeine in healthy volunteers: implications for drugs-of-abuse testing. Journal of analytical toxicology. 1996 Nov; 20(7):541-6. doi: 10.1093/jat/20.7.541. [PMID: 8934303]
  • R W Romberg, L Lee. Comparison of the hydrolysis rates of morphine-3-glucuronide and morphine-6-glucuronide with acid and beta-glucuronidase. Journal of analytical toxicology. 1995 May; 19(3):157-62. doi: 10.1093/jat/19.3.157. [PMID: 7564293]
  • T B Vree, C P Verwey-van Wissen. Pharmacokinetics and metabolism of codeine in humans. Biopharmaceutics & drug disposition. 1992 Aug; 13(6):445-60. doi: 10.1002/bdd.2510130607. [PMID: 1391681]
  • C P Verwey-van Wissen, P M Koopman-Kimenai, T B Vree. Direct determination of codeine, norcodeine, morphine and normorphine with their corresponding O-glucuronide conjugates by high-performance liquid chromatography with electrochemical detection. Journal of chromatography. 1991 Oct; 570(2):309-20. doi: 10.1016/0378-4347(91)80534-j. [PMID: 1797846]
  • Z R Chen, A A Somogyi, G Reynolds, F Bochner. Disposition and metabolism of codeine after single and chronic doses in one poor and seven extensive metabolisers. British journal of clinical pharmacology. 1991 Apr; 31(4):381-90. doi: 10.1111/j.1365-2125.1991.tb05550.x. [PMID: 2049245]
  • A Somogyi, F Bochner, Z R Chen. Lack of effect of paracetamol on the pharmacokinetics and metabolism of codeine in man. European journal of clinical pharmacology. 1991; 41(4):379-82. doi: 10.1007/bf00314972. [PMID: 1804656]
  • K Oguri, N Hanioka, H Yoshimura. Species differences in metabolism of codeine: urinary excretion of codeine glucuronide, morphine-3-glucuronide and morphine-6-glucuronide in mice, rats, guinea pigs and rabbits. Xenobiotica; the fate of foreign compounds in biological systems. 1990 Jul; 20(7):683-8. doi: 10.3109/00498259009046884. [PMID: 2238703]
  • Z R Chen, G Reynolds, F Bochner, A Somogyi. Direct determination of codeine-6-glucuronide in plasma and urine using solid-phase extraction and high-performance liquid chromatography with fluorescence detection. Journal of chromatography. 1989 Sep; 493(2):313-24. doi: 10.1016/s0378-4347(00)82737-1. [PMID: 2584298]