AM404
From Wikipedia, the free encyclopedia
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| Systematic (IUPAC) name | |
| (5Z,8Z,11Z,14Z)- N-(4-hydroxyphenyl)icosa- 5,8,11,14-tetraenamide | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 183718-77-6 198022-70-7 |
| ATC code | ? |
| PubChem | CID 6604822 |
| ChemSpider | 5037081  |
| ChEMBL | CHEMBL39878 |
| Chemical data | |
| Formula | C26H37NO2 |
| Mol. mass | 395.577 g/mol |
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AM404, also known as N-arachidonoylaminophenol,[1] is an active metabolite of paracetamol (acetaminophen), responsible for all or part of its analgesic action.[2]
[edit] 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.[3]
AM404 is also a TRPV1 agonist and inhibitor of cyclooxygenase COX-1 and COX-2, thus attenuating prostaglandin synthesis. AM404 is thought to induce its analgesic action through its activity on the endocannabinoid, COX, and TRPV systems, all of which are present in pain and thermoregulatory pathways.[4]
[edit] See also
[edit] References
- ^ Rogosch, Tobias; et al. (January 2012). "Novel bioactive metabolites of dipyrone (metamizol)". Bioorg. Med. Chem. 20 (1): 101–107. doi:10.1016/j.bmc.2011.11.028. PMC 3248997. PMID 22172309. Retrieved 26 January 2013.
- ^ 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". European Journal of Pharmacology 531 (1–3): 280–281. doi:10.1016/j.ejphar.2005.12.015. PMID 16438952.
- ^ 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 (7): 4269–4274. Bibcode:2003PNAS..100.4269G. doi:10.1073/pnas.0730816100. PMC 153082. PMID 12655057.
- ^ Högestätt, E. D.; Jönsson, B. A.; Ermund, A.; Andersson, D. A.; Björk, H.; Alexander, J. P.; Cravatt, B. F.; Basbaum, A. I. et al. (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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