Morphine-6-glucuronide

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Morphine-6-glucuronide
Morphine-6-glucuronide2DCSD.svg
Names
Other names
M6G
Identifiers
20290-10-2 N
ChEMBL ChEMBL1330 YesY
ChemSpider 4514548 YesY
Jmol 3D model Interactive image
MeSH Morphine-6-glucuronide
PubChem 5360621
  • 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 YesY
    Key: GNJCUHZOSOYIEC-GAROZEBRSA-N YesY
  • InChI=1/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
    Key: GNJCUHZOSOYIEC-GAROZEBRBC
  • O=C(O)[C@H]6O[C@@H](O[C@H]1/C=C\[C@@H]5[C@@]24c3c(ccc(O)c3O[C@@H]12)C[C@H]5N(C)CC4)[C@H](O)[C@@H](O)[C@@H]6O
Properties
C23H27NO9
Molar mass 461.46 g/mol
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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 heroin[citation needed] - M6G is formed from morphine by the enzyme UDP-Glucuronosyltransferase-2B7 (UGT2B7). M6G can accumulate to toxic levels in kidney failure.[1][2]

History of discovery

This analgesic activity of M6G (in animals) was first noted by Yoshimura.[3]

Subsequent work at St Bartholomew's Hospital, London in the 1980s,[4] using a sensitive and specific HPLC assay,[5] accurately defined for the first time the metabolism of morphine, and the abundance of this metabolite (along with morphine-3-glucuronide,[6] considered an inactive metabolite).

It was postulated that renal impairment would result in accumulation of the renally-excreted active agent M6G, leading to potentially fatal toxicity such as respiratory depression. The frequent use of morphine in critically ill patients, and the common occurrence of renal failure in this group implied that M6G accumulation could be a common, but previously unanticipated problem. The first studies demonstrated massive levels of M6G in 3 patients with renal failure, which resolved as kidney function returned.[1] Accumulation of M3G and M6G also decrease with return of renal function after renal transplantation.[2]

A key step in defining the importance of M6G in humans came in 1992 when the substance was artificially synthesised and administered to patients with pain, the majority of whom described pain relief.[7]

See also

References

  1. ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Renal tubular transport of morphine, morphine-6-glucuronide, and morphine-3-glucuronide in the isolated perfused rat kidney. JT Van Crugten, BC Sallustio, RL Nation and AA Somogyi. Department of Clinical and Experimental Pharmacology, University of Adelaide, Australia.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.


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