Tobias Rogosch - Novel bioactive metabolites of dipyrone (metamizol).

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  Publication Details (including relevant citation   information):

  Rogosch T, Sinning C, Podlewski A, Watzer B, Schlosburg J,   Lichtman AH, Cascio MG, Bisogno T, Di Marzo V, Nüsing R, Imming   P.

  Bioorg Med Chem.   2012 Jan 1;20(1):101-7.

  doi: 10.1016/j.bmc.2011.11.028


  Dipyrone is a common antipyretic drug and the most popular   non-opioid analgesic in many countries. In spite of its long and   widespread use, molecular details of its fate in the body are not   fully known. We administered dipyrone orally to mice. Two unknown   metabolites were found, viz. the arachidonoyl amides of the known   major dipyrone metabolites, 4-methylaminoantipyrine (2) and   4-aminoantipyrine (3). They were identified by ESI-LC-MS/MS after   extraction from the CNS, and comparison with reference substances   prepared synthetically. The arachidonoyl amides were positively   tested for cannabis receptor binding (CB(1) and CB(2)) and   cyclooxygenase inhibition (COX-1 and COX-2 in tissues and as   isolated enzymes), suggesting that the endogenous cannabinoid   system may play a role in the effects of dipyrone against pain.

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