Morphine-3-glucuronide
 | |
| Identifiers | |
|---|---|
| 3D model (JSmol) |
|
| ChemSpider | |
| ECHA InfoCard | 100.150.265 |
| MeSH | Morphine-3-glucuronide |
| PubChem CID |
|
| |
| |
| Properties | |
| C23H27NO9 | |
| Molar mass | 461.462 g/mol |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is  ?) | |
| Infobox references | |
Morphine-3-glucuronide is a metabolite of morphine produced by UGT2B7. It is not active as an opioid agonist,[1] but does have some action as a convulsant, which does not appear to be mediated through opioid receptors,[2] but rather through interaction with glycine and/or GABA receptors. As a polar compound, it has a limited ability to cross the blood–brain barrier, but renal failure may lead to its accumulation and result in seizures. Probenecid and inhibitors of P-glycoprotein can enhance uptake of morphine-3-glucuronide and, to a lesser extent, morphine-6-glucuronide.[3] Reported side effects related to the accumulation of this metabolite include convulsions, agitation, hallucinations, hyperalgesia, and coma.
See also
- Morphine-6-glucuronide
- 3-Monoacetylmorphine, the inactive 3,- position blocked by esterization (and thus inactive) of a semi-synthetic prodrug to morphine marking the same activity profile as the drug of this article
- Morphine-N-oxide
- Buprenorphine-3-glucuronide
References
- ↑ Vindenes V, Ripel A, Handal M, Boix F, Mørland J (July 2009). "Interactions between morphine and the morphine-glucuronides measured by conditioned place preference and locomotor activity". Pharmacology, Biochemistry, and Behavior. 93 (1): 1–9. PMID 19351545. doi:10.1016/j.pbb.2009.03.013.
- ↑ Hemstapat K, Le L, Edwards SR, Smith MT (July 2009). "Comparative studies of the neuro-excitatory behavioural effects of morphine-3-glucuronide and dynorphin a(2-17) following spinal and supraspinal routes of administration". Pharmacology, Biochemistry, and Behavior. 93 (4): 498–505. PMID 19580825. doi:10.1016/j.pbb.2009.06.016.
- ↑ Bertram G. Katzung; Susan B. Masters; Anthony J. Trevor. Basic & Clinical Pharmacology (11th ed.).
This article is issued from
Wikipedia.
The text is licensed under Creative Commons - Attribution - Sharealike.
Additional terms may apply for the media files.