Phenazone

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Structural formula
Structural formula phenazone
General
Non-proprietary name Phenazone
other names
  • Antipyrine
  • Phenazonum ( Latin )
  • 1,5-dimethyl-2-phenyl-2,3-dihydro-1 H -pyrazol-3-one ( IUPAC )
  • 1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one ( pharmacopoeia )
  • 2,3-dimethyl-1-phenyl-3-pyrazolin-5-one (WHO)
Molecular formula C 11 H 12 N 2 O
Brief description

white solid

External identifiers / databases
CAS number 60-80-0
EC number 200-486-6
ECHA InfoCard 100,000,442
PubChem 2206
DrugBank DB01435
Wikidata Q415578
Drug information
ATC code

N02 BB01

properties
Molar mass 188.23 g mol −1
Physical state

firmly

density

1.19 g cm −3 (at 20 ° C)

Melting point

111-114 ° C

boiling point

319 ° C (at 230 hPa)

solubility

very good in water (1700 g l −1 at 20 ° C)

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: 260-270-301-101
Toxicological data

1705 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Phenazone (former brand name: antipyrine ) is a pyrazolone - derivative and in human and veterinary medicine as analgesics (will analgesic ), and antipyretic agent ( an antipyretic ) was used.

properties

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.

use

Phenazon is an analgesic from the group of pyrazolones . It is the oldest synthetic, weakly effective analgesic and, in addition to its analgesic, it also has an antipyretic ( antipyretic ) effect.

history

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 .

See also

Individual evidence

  1. ↑ a b Phenazon data sheet from AlfaAesar, accessed on December 15, 2010 ( PDF )(JavaScript required) .
  2. ↑ Data sheet Antipyrine from Sigma-Aldrich , accessed on May 12, 2017 ( PDF ).
  3. ↑ a b c d e f Entry on phenazone in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
  4. ^ 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.
  5. ↑ a b MDR: History of Central Germany Ludwig Knorr (1859-1921) ( Memento from July 21, 2007 in the Internet Archive ).
  6. ↑ Andreas Jehkul: Clinical-pharmacological studies on the pharmacodynamics and pharmacokinetics of codeine and propyphenazone on test subjects and patients. , Dissertation, University of Heidelberg 2002. DNB 96615214x / 34 p. 16 with additional information
  7. ↑ Lexicon of Biology: Aminophenazon .

Trade names

Monopreparations

Eu-Med (D), Migräne-Kranit 500mg tablets / suppositories (D), Migraine Phenazon (D)

Combination preparations

Coffo-Selt (A), Otalgan (D, A, CH), Otipax (CH), Otosan (CH), Otothricinol (CH)