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AM404
Systematic (IUPAC) name
(5Z,8Z,11Z,14Z)- N-(4-hydroxyphenyl)icosa- 5,8,11,14-tetraenamide
Identifiers
CAS number 183718-77-6 198022-70-7
ATC code  ?
PubChem 6604822
ChemSpider 5037081
Chemical data
Formula C 26H37NO2  
Mol. mass 395.577 g/mol
SMILES eMolecules & PubChem
Synonyms N-arachidonoyl- phenolamine
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Metabolite of OTC drug
Routes  ?
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AM404 also known as N-arachidonoylphenolamine is an active metabolite of paracetamol (acetaminophen) responsible for all or part of its analgesic action.[1]

Pharmacology

AM404 was originally reported to be an endogenous cannabinoid reuptake inhibitor, preventing the transport of anandamide and other related compounds back from the synaptic cleft, much in the same way that common SSRI antidepressants prevent the reuptake of serotonin. Recent work on the mechanism of AM404 has suggested that the inhibition of fatty acid amide hydrolase (FAAH) by AM404 is likely responsible for all of its attributed "reuptake" properties, since intracellular FAAH hydrolysis of anandamide changes the intra/extracellular anandamide equilibrium.[2]

AM404 is also TRPV1 agonist, and also prevents cyclooxygenase COX-1 and COX-2 and prostaglandin synthesis. AM404 is thought to induce its analgesic action through its activity on the cannabinoid, COX and TRPV systems, all of which are present in pain and thermoregulatory pathways.[3]

References

  1. ^ Ottani A, Leone S, Sandrini M, Ferrari A, Bertolini A (2006). "The analgesic activity of paracetamol is prevented by the blockade of cannabinoid CB1 receptors". Eur. J. Pharmacol. 531 (1-3): 280–1. doi:10.1016/j.ejphar.2005.12.015. PMID 16438952.  
  2. ^ Glaser, S. T.; Abumrad, N. A.; Fatade, F.; Kaczocha, M.; Studholme, K. M.; Deutsch, D. G. (2003). "Evidence against the presence of an anandamide transporter". Proceedings of the National Academy of Sciences 100: 4269. doi:10.1073/pnas.0730816100.   edit
  3. ^ Högestätt, E. D., B. A. G. Jönsson, A. Ermund, D. A. Andersson, H. Björk, J. P. Alexander, B. F. Cravatt, A. I. Basbaum, P. M. Zygmunt (September 9, 2005). "Conversion of Acetaminophen to the Bioactive N-Acylphenolamine AM404 via Fatty Acid Amide Hydrolase-dependent Arachidonic Acid Conjugation in the Nervous System". Journal of Biological Chemistry 280 (36): 31405–31412. doi:10.1074/jbc.M501489200. PMID 15987694.  







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