Codeine and morphine metabolism (Homo sapiens)

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2, 3, 8, 18, 22...4, 17, 19, 205, 24127, 14, 2113Elimination via bileLiver cellUGT2B7Morphine-3-glucuronideMorphine-6-glucuronideCodeine-6-glucuronideNorcodeineNormorphineABCC2Morphine-6-glucuronideUGT2B7CYP2D7P1Morphine-3-glucuronideCYP3A4UGT1A1MorphineUGT2B7UGT1A1Codeine-6-glucuronideABCC3ABCB1SLCO1B1CodeineCYP2D6219-11, 15, 1661, 25


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Bibliography

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  1. Loetsch J, Stockmann A, Kobal G, Brune K, Waibel R, Schmidt N, Geisslinger G; ''Pharmacokinetics of morphine and its glucuronides after intravenous infusion of morphine and morphine-6-glucuronide in healthy volunteers.''; Clin Pharmacol Ther, 1996 PubMed Europe PMC Scholia
  2. Maurer HH, Sauer C, Theobald DS; ''Toxicokinetics of drugs of abuse: current knowledge of the isoenzymes involved in the human metabolism of tetrahydrocannabinol, cocaine, heroin, morphine, and codeine.''; Ther Drug Monit, 2006 PubMed Europe PMC Scholia
  3. Xie R, Hammarlund-Udenaes M, de Boer AG, de Lange EC; ''The role of P-glycoprotein in blood-brain barrier transport of morphine: transcortical microdialysis studies in mdr1a (-/-) and mdr1a (+/+) mice.''; Br J Pharmacol, 1999 PubMed Europe PMC Scholia
  4. Coffman BL, Rios GR, King CD, Tephly TR; ''Human UGT2B7 catalyzes morphine glucuronidation.''; Drug Metab Dispos, 1997 PubMed Europe PMC Scholia
  5. Sawyer MB, Innocenti F, Das S, Cheng C, Ramirez J, Pantle-Fisher FH, Wright C, Badner J, Pei D, Boyett JM, Cook E Jr, Ratain MJ; ''A pharmacogenetic study of uridine diphosphate-glucuronosyltransferase 2B7 in patients receiving morphine.''; Clin Pharmacol Ther, 2003 PubMed Europe PMC Scholia
  6. Meineke I, Freudenthaler S, Hofmann U, Schaeffeler E, Mikus G, Schwab M, Prange HW, Gleiter CH, Brockmoeller J; ''Pharmacokinetic modelling of morphine, morphine-3-glucuronide and morphine-6-glucuronide in plasma and cerebrospinal fluid of neurosurgical patients after short-term infusion of morphine.''; Br J Clin Pharmacol, 2002 PubMed Europe PMC Scholia
  7. Yue QY, Hasselstroem J, Svensson JO, Saewe J; ''Pharmacokinetics of codeine and its metabolites in Caucasian healthy volunteers: comparisons between extensive and poor hydroxylators of debrisoquine.''; Br J Clin Pharmacol, 1991 PubMed Europe PMC Scholia
  8. Ohno S, Kawana K, Nakajin S; ''Contribution of UDP-glucuronosyltransferase 1A1 and 1A8 to morphine-6-glucuronidation and its kinetic properties.''; Drug Metab Dispos, 2008 PubMed Europe PMC Scholia
  9. Bourasset F, Cisternino S, Temsamani J, Scherrmann JM; ''Evidence for an active transport of morphine-6-beta-d-glucuronide but not P-glycoprotein-mediated at the blood-brain barrier.''; J Neurochem, 2003 PubMed Europe PMC Scholia
  10. Bhasker CR, McKinnon W, Stone A, Lo AC, Kubota T, Ishizaki T, Miners JO; ''Genetic polymorphism of UDP-glucuronosyltransferase 2B7 (UGT2B7) at amino acid 268: ethnic diversity of alleles and potential clinical significance.''; Pharmacogenetics, 2000 PubMed Europe PMC Scholia
  11. Madadi P, Koren G; ''Pharmacogenetic insights into codeine analgesia: implications to pediatric codeine use.''; Pharmacogenomics, 2008 PubMed Europe PMC Scholia
  12. Zelcer N, van de Wetering K, Hillebrand M, Sarton E, Kuil A, Wielinga PR, Tephly T, Dahan A, Beijnen JH, Borst P; ''Mice lacking multidrug resistance protein 3 show altered morphine pharmacokinetics and morphine-6-glucuronide antinociception.''; Proc Natl Acad Sci U S A, 2005 PubMed Europe PMC Scholia
  13. Pai HV, Kommaddi RP, Chinta SJ, Mori T, Boyd MR, Ravindranath V; ''A frameshift mutation and alternate splicing in human brain generate a functional form of the pseudogene cytochrome P4502D7 that demethylates codeine to morphine.''; J Biol Chem, 2004 PubMed Europe PMC Scholia
  14. Milne RW, Nation RL, Somogyi AA; ''The disposition of morphine and its 3- and 6-glucuronide metabolites in humans and animals, and the importance of the metabolites to the pharmacological effects of morphine.''; Drug Metab Rev, 1996 PubMed Europe PMC Scholia
  15. Chen ZR, Somogyi AA, Reynolds G, Bochner F; ''Disposition and metabolism of codeine after single and chronic doses in one poor and seven extensive metabolisers.''; Br J Clin Pharmacol, 1991 PubMed Europe PMC Scholia
  16. Innocenti F, Liu W, Fackenthal D, Ramirez J, Chen P, Ye X, Wu X, Zhang W, Mirkov S, Das S, Cook E Jr, Ratain MJ; ''Single nucleotide polymorphism discovery and functional assessment of variation in the UDP-glucuronosyltransferase 2B7 gene.''; Pharmacogenet Genomics, 2008 PubMed Europe PMC Scholia
  17. Caraco Y, Tateishi T, Guengerich FP, Wood AJ; ''Microsomal codeine N-demethylation: cosegregation with cytochrome P4503A4 activity.''; Drug Metab Dispos, 1996 PubMed Europe PMC Scholia
  18. Skarke C, Schmidt H, Geisslinger G, Darimont J, Loetsch J; ''Pharmacokinetics of morphine are not altered in subjects with Gilbert's syndrome.''; Br J Clin Pharmacol, 2003 PubMed Europe PMC Scholia
  19. Desmeules J, Gascon MP, Dayer P, Magistris M; ''Impact of environmental and genetic factors on codeine analgesia.''; Eur J Clin Pharmacol, 1991 PubMed Europe PMC Scholia
  20. Koren G, Cairns J, Chitayat D, Gaedigk A, Leeder SJ; ''Pharmacogenetics of morphine poisoning in a breastfed neonate of a codeine-prescribed mother.''; Lancet, 2006 PubMed Europe PMC Scholia
  21. Madadi P, Ross CJ, Hayden MR, Carleton BC, Gaedigk A, Leeder JS, Koren G; ''Pharmacogenetics of neonatal opioid toxicity following maternal use of codeine during breastfeeding: a case-control study.''; Clin Pharmacol Ther, 2009 PubMed Europe PMC Scholia
  22. Court MH, Krishnaswamy S, Hao Q, Duan SX, Patten CJ, Von Moltke LL, Greenblatt DJ; ''Evaluation of 3'-azido-3'-deoxythymidine, morphine, and codeine as probe substrates for UDP-glucuronosyltransferase 2B7 (UGT2B7) in human liver microsomes: specificity and influence of the UGT2B7*2 polymorphism.''; Drug Metab Dispos, 2003 PubMed Europe PMC Scholia
  23. Gasche Y, Daali Y, Fathi M, Chiappe A, Cottini S, Dayer P, Desmeules J; ''Codeine intoxication associated with ultrarapid CYP2D6 metabolism.''; N Engl J Med, 2004 PubMed Europe PMC Scholia
  24. Darbari DS, van Schaik RH, Capparelli EV, Rana S, McCarter R, van den Anker J; ''UGT2B7 promoter variant -840G>A contributes to the variability in hepatic clearance of morphine in patients with sickle cell disease.''; Am J Hematol, 2008 PubMed Europe PMC Scholia
  25. Holthe M, Klepstad P, Zahlsen K, Borchgrevink PC, Hagen L, Dale O, Kaasa S, Krokan HE, Skorpen F; ''Morphine glucuronide-to-morphine plasma ratios are unaffected by the UGT2B7 H268Y and UGT1A1*28 polymorphisms in cancer patients on chronic morphine therapy.''; Eur J Clin Pharmacol, 2002 PubMed Europe PMC Scholia
  26. Loetsch J, Skarke C, Liefhold J, Geisslinger G; ''Genetic predictors of the clinical response to opioid analgesics: clinical utility and future perspectives.''; Clin Pharmacokinet, 2004 PubMed Europe PMC Scholia

History

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CompareRevisionActionTimeUserComment
128156view16:57, 28 January 2024EweitzEconomize layout
128155view16:54, 28 January 2024EweitzImprove alignment, economize layout
128154view16:48, 28 January 2024EweitzStandardize shapes
128153view16:45, 28 January 2024EweitzOntology Term : 'hepatocyte' added !
125609view10:33, 4 March 2023EgonwMinor updates to modern drawing standards.
118374view13:50, 27 May 2021Mkutmonfix references
116814view10:12, 14 May 2021EweitzModified title
110711view14:49, 28 May 2020Fehrhartchanged node to label for Gilbert syndrome
106699view13:09, 17 September 2019MaintBotHMDB identifier normalization
98130view08:58, 25 July 2018DeSlAdded stereochemically correct ID for Norcodeine; changed layout slightly due to overlapping references on nodes.
98129view07:56, 25 July 2018DeSlOntology Term : 'Gilbert syndrome' added !
95222view18:21, 26 November 2017DeSlRemoved licence number
95221view18:19, 26 November 2017DeSlConnected unconnected line.
95202view14:47, 22 November 2017DeSlModified description
95201view14:37, 22 November 2017DeSlModified description
95200view14:34, 22 November 2017DeSlAdded OMIM IDs for diseases
95199view14:34, 22 November 2017DeSlModified description
95198view14:32, 22 November 2017DeSlAdded additional enzym information from new literature source.
89511view10:44, 16 September 2016Mkutmonontology tag fix
89468view13:39, 15 September 2016Mkutmonremove space from ontology term id
74317view13:50, 12 April 2014EgonwFixed a character encoding issue.
69899view19:27, 11 July 2013AlexanderPicoCleaned up interactions
69895view19:18, 11 July 2013AlexanderPicoModified title
67120view10:09, 26 June 2013Christine ChichesterOntology Term : 'codeine and morphine drug pathway' added !
63436view15:40, 10 May 2013EgonwAdded other missing metabolite identifiers (from HMDB and PubChem)
63435view15:08, 10 May 2013EgonwAdded a HMDB id for morphine.
63165view20:24, 8 May 2013MaintBotUpdating gpml version
59205view19:45, 22 February 2013MaintBotUpdated Ensembl data source
44994view14:37, 6 October 2011MartijnVanIerselOntology Term : 'xenobiotics biodegradation pathway' added !
44993view14:37, 6 October 2011MartijnVanIerselOntology Term : 'drug pathway' added !
41197view23:43, 1 March 2011MaintBotRemoved redundant pathway information and comments
38483view18:24, 17 September 2010AlexanderPicoModified description
38351view22:51, 1 September 2010KhanspersModified categories
38350view22:51, 1 September 2010KhanspersChanged literature references
38349view22:47, 1 September 2010KhanspersModified description
38348view22:39, 1 September 2010KhanspersNew pathway

External references

DataNodes

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NameTypeDatabase referenceComment
ABCB1GeneProduct5243 (Entrez Gene)
ABCC2GeneProduct1244 (Entrez Gene)
ABCC3GeneProduct8714 (Entrez Gene)
CYP2D6GeneProduct1565 (Entrez Gene)
CYP2D7P1GeneProductENSG00000205702 (Ensembl Human)
CYP3A4GeneProduct1576 (Entrez Gene)
Codeine-6-glucuronideMetabolite
CodeineMetaboliteHMDB04995 (HMDB)
MorphineMetabolite
Morphine-3-glucuronideMetabolite
Morphine-6-glucuronideMetabolite
NorcodeineMetabolite
NormorphineMetabolite
SLCO1B1GeneProduct10599 (Entrez Gene)
UGT1A1GeneProduct54658 (Entrez Gene)
UGT2B7GeneProduct7364
UGT2B7GeneProduct7364 (Entrez Gene)

Annotated Interactions

No annotated interactions

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