|Molecular formula||C 11 H 12 N 2 O|
|External identifiers / databases|
|Molar mass||188.23 g mol −1|
1.19 g cm −3 (at 20 ° C)
111-114 ° C
319 ° C (at 230 hPa)
very good in water (1700 g l −1 at 20 ° C)
|As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .|
Phenazon is a white, odorless, crystalline powder that dissolves very well in water (1700 g / l at 20 ° C). The substance melts at 111 to 114 ° C and boils at 319 ° C. With further heating, decomposition occurs from 360 ° C.
Phenazone was first synthesized in 1883 at the suggestion of Wilhelm Filehne by Emil Fischer's assistant Ludwig Knorr in an attempt to find a quinoline derivative with fewer side effects than the fever-lowering quinine . The pyrazolone phenazone was registered for a patent by Farbwerke Hoechst in 1883 and then marketed under the brand name Antipyrin ® . The pharmaceutical division of Höchst Farbwerke and ultimately the entire German pharmaceutical industry owes its rise to this drug. The substance was further developed by Hoechst in 1896 into the three times more effective aminophenazone ( pyramidone ), which according to the state of knowledge at the time also had fewer side effects. Since 1978, however, aminophenazone has not been approved in human medicine in Germany and Switzerland due to its carcinogenicity . 1922 followed with the metamizole (Novalgin ® ) another further development of the phenazone by Hoechst, 1933 with Hoffmann-La Roches propyphenazone (Saridon ® , in combination with phenacetin , pyrithyldione and caffeine ) an active substance, to which after the deletion of the aminophenazone reinforced as a substitute was resorted to. Phenazone as the original substance is still marketed in a few preparations, for example under the brand name Migraine- Kranit ® 500mg by Krewel Meuselbach .
- Data sheet Antipyrine from Sigma-Aldrich , accessed on May 12, 2017 ( PDF ).
- Doris Schwarzmann-Schafhauser: Antipyrin. In: Werner E. Gerabek u. a. (Ed.): Encyclopedia of medical history. De Gruyter, Berlin / New York 2005, ISBN 3-11-015714-4 , p. 72.
- MDR: History of Central Germany Ludwig Knorr (1859-1921) ( Memento from July 21, 2007 in the Internet Archive ).
- Andreas Jehkul: Clinical-pharmacological studies on the pharmacodynamics and pharmacokinetics of codeine and propyphenazone on test subjects and patients. , Dissertation, University of Heidelberg 2002. p. 16 with
- Lexicon of Biology: Aminophenazon .
Eu-Med (D), Migräne-Kranit 500mg tablets / suppositories (D), Migraine Phenazon (D)
Coffo-Selt (A), Otalgan (D, A, CH), Otipax (CH), Otosan (CH), Otothricinol (CH)