The Full Wiki

More info on Morphine-6-glucuronide

Morphine-6-glucuronide: Wikis

Advertisements
  

Note: Many of our articles have direct quotes from sources you can cite, within the Wikipedia article! This article doesn't yet, but we're working on it! See more info or our list of citable articles.

Encyclopedia

From Wikipedia, the free encyclopedia

Morphine-6-glucuronide
Morphine 6-glucuronide.png
Other names M6G
Identifiers
CAS number 20290-10-2
PubChem 5360621
MeSH Morphine-6-glucuronide
SMILES
Properties
Molecular formula C23H27NO9
Molar mass 461.46 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 thus heroin and codeine). This analgesic activity of M6G (in animals) was first noted by Yoshimura.[1]

Subsequent work at St Bartholomew's Hospital, London in the 1980s,[2] using a sensitive and specific HPLC assay,[3] accurately defined for the first time the metabolism of morphine, and the abundance of this metabolite (along with morphine-3-glucuronide[4] and morphine-3,6-diglucuronide, both considered inactive metabolites).

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.[5] Subsequent work formally examined the role of renal function in the pharmacokinetics of morphine and its metabolites by studying their behaviour before and after renal transplantation.[6]

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

References

  1. ^ Hidetoshi, Y (1969). "Metabolism of drugs. LXII. Isolation and identification of morphine glucuronides in urine and bile of rabbits". Biochem Pharmacol 18: 279–86. doi:10.1016/0006-2952(69)90205-6.  
  2. ^ "Morphine and metabolite behavior after different routes of morphine administration: demonstration of the importance of the active metabolite morphine-6-glucuronide". Clin Pharmacol Ther. 47: 12–9. 1990.  
  3. ^ Joel, S (1988). "An improved method for the simultaneous determination of morphine and its principal glucuronide metabolites". J Chromatogr 430: 394–9. doi:10.1016/S0378-4347(00)83176-X.  
  4. ^ 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.
  5. ^ Osborne, R J (1986). "Morphine intoxication in renal failure: the role of morphine-6-glucuronide". Br Med J 292: 1548–9. doi:10.1136/bmj.292.6535.1548. PMID 3087512.  
  6. ^ "The pharmacokinetics of morphine and morphine glucuronides in kidney failure". Clin Pharmacol Ther 54: 158–67. 1993.  
  7. ^ "The analgesic activity of morphine-6-glucuronide". Br J Clin Pharmacol 34: 130–8. 1992.  
Advertisements

Advertisements






Got something to say? Make a comment.
Your name
Your email address
Message