Morphine-6-glucuronide

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Morphine-6-glucuronide
Names
Other names
M6G
Identifiers
3D model (
JSmol
)
ChEMBL
ChemSpider
ECHA InfoCard
 100.161.871 Edit this at Wikidata
MeSH Morphine-6-glucuronide
UNII
  • 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 checkY
    Key: GNJCUHZOSOYIEC-GAROZEBRSA-N checkY
  • 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Morphine-6-glucuronide (M6G) is a major active metabolite of morphine. M6G is formed from morphine by the enzyme UGT2B7.[1] It has analgesic effects more potent than morphine.[2] M6G can accumulate to toxic levels in kidney failure.[3][4]

History of discovery

This analgesic activity of M6G (in animals) was first noted by Yoshimura.[5]

Subsequent work at

high-performance liquid chromatography assay,[7] accurately defined for the first time the metabolism of morphine, and the abundance of this metabolite (along with morphine-3-glucuronide,[8]
considered an inactive metabolite).

It was postulated that kidney impairment would result in accumulation of the kidney-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 kidney 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 kidney failure, which resolved as kidney function returned.[3] Accumulation of M3G and M6G also decreased with return of kidney function after kidney transplantation.[4]

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.[9]

See also

References

  1. PMID 9010622
    .
  2. S2CID 18890026
    .
  3. ^
    PMID 3087512
    .
  4. ^
    S2CID 44954994
    .
  5. PMID 5778147
    .
  6. S2CID 37751253
    .
  7. PMID 3235512
    .
  8. ^ 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.
  9. PMID 1419474
    .
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