Die Stoffwechselprodukte des Pyramidons und verwandter Verbindungen beim Menschen

Halberkann, J.; Fretwurst, F.

doi:10.1515/bchm2.1950.285.1-3.97

Cited by 46 publications

(6 citation statements)

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“…In one case 23% was found (Halberkann & Fretwurst, 1950). The excretion of both substances, extends over 4-5 days.…”

Section: Aminopyrinementioning

confidence: 89%

“…The most important reactions in man are: (1) demethylation at the 4-position of the pyrazolone ring with formation of 4-methylaminoantipyrine and 4-aminoantipyrine (Brodie & Axelrod, 1950;Halberkann & Fretwurst, 1950;Schuppel & Soehring, 1965;Pechthold, 1964a); and (2) acylation of these compounds to 4-acetylaminoantipyrine (Brodie & Axelrod, 1950;Halberkann & Fretwurst, 1950) and 4-formylaminoantipyrine (Iguchi, Goromaru & Noda, 1975 Quantities of 4-aminoantipyrine (4-8% of the dose) in the urine are usually reported. In one case 23% was found (Halberkann & Fretwurst, 1950).…”

Section: Aminopyrinementioning

confidence: 99%

“…On the other hand, the share of 4-formylaminoantipyrine accounts for up to 20%. Quantitatively less important metabolites include 4-acetylmethylaminoantipyrine (Vecerkova, Kakac, Vecerek & Ledvina, 1967), 4-hydroxyantipyrine (Brodie & Axelrod, 1950;Halberkann & Fretwurst, 1950;Gradnik & Fleischmann, 1973), predominantly excreted conjugated with glucuronide or sulphate, and also rubazonic and methylrubazonic acid (Jaffe, 1901;Schuppel & Soehring, 1965;Pechtold, 1964b;Preuss & Voigt, 1965). The latter occur only sporadically and it has not been finally clarified whether they are artefacts or true metabolites of aminopyrine.…”

Section: Aminopyrinementioning

confidence: 99%

“…The following have been investigated: rat (Schuppel & Soehring, 1965;Klinger, 1969;Yoshimura, Shimeno & Tsukamoto, 1970;Niwa, Hikichi & Sasaki, 1975) dog (Halberkann & Fretwurst, 1950;Pechthold, 1964a;Schuppel & Soehring, 1965) and rabbit (Yoshimura et al, 1970;Niwa et al, 1975). Although rat and rabbit are similar to man 4-aminoantipyrine and its 4-acetyland formyl-derivative are the main metabolites -the dog behaves quite differently.…”

Section: Aminopyrinementioning

confidence: 99%

“…Only small quantities of 4-acetylaminoantipyrine (0-5%0) occur in the urine. The chief products (approximately 89%o) are the original substance and 4-aminoantipyrine (10qo) (Halberkann & Fretwurst, 1950). Yoshimura et al (1970) have reported three further minor aminoantipyrine metabolites in rats and rabbits ( Figure 6) which are formed by oxidation of the methyl group on the C-3 atom.…”

Section: Aminopyrinementioning

confidence: 99%

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Kinetics and metabolism of pyrazolones (propyphenazone, aminopyrine and dipyrone).

Volz¹,

Kellner²

1980

Brit J Clinical Pharma

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1 Propyphenazone 220 mg was administered orally to volunteers. Maximum plasma concentrations between 1.5 ,ug/ml and 3.5 Hg/ml were found 30 min later. After comparable doses plasma concentrations in dog and rabbit were lower. The distribution volumes were 2 1/kg. 2 The major metabolic route of propyphenazone is demethylation. The main urinary metabolite is the enolglucuronide of N-(2)-demethylpropyphenazone. 3 Aminopyrine is rapidly and almost completely absorbed after oral administration. Maximum plasma concentrations of 10 .g/ml are reached 1.5 h after a 500 mg dose. The biological half-life is 2-3 h, the relative distribution volume 6007 on average, and binding to plasma proteins approximately 15%. 4 Unchanged aminopyrine is only excreted in small quantities. The major routes of metabolism are demethylation (4-methylaminoantipyrine and 4-aminoantipyrine) and acylation (4-acetyl and 4-formylaminoantipyrine). There are other biotransformation products. 5 After oral administration of [14C]-dipyrone 480 mg the maximum serum concentration of 13.4±0.8 ,ug/ml occurred at 1-1.5 hours. 6 Dipyrone was not detectable in serum or urine. Four of seven metabolites were identified, and were identical with the main metabolites of aminopyrine.

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“…In one case 23% was found (Halberkann & Fretwurst, 1950). The excretion of both substances, extends over 4-5 days.…”

Section: Aminopyrinementioning

confidence: 89%

Section: Aminopyrinementioning

confidence: 99%

Section: Aminopyrinementioning

confidence: 99%

Section: Aminopyrinementioning

confidence: 99%

Section: Aminopyrinementioning

confidence: 99%

See 3 more Smart Citations

Kinetics and metabolism of pyrazolones (propyphenazone, aminopyrine and dipyrone).

Volz¹,

Kellner²

1980

Brit J Clinical Pharma

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1964

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Strukturabwandlung von Analgetika durch Aminomethinylierung

Kreutzberger

1974

Archiv der Pharmazie

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Suspendierte man 2,6 g 12 in 10 ml mit Wasscr gesittigtem Ather und lie6 in offener Schale verdunsten, so wurden die gelben Kristalle ziegelrot. Man nahm in Ather auf, filtrierte, lie6 erneut verdunsten und trennte die ausgcschiedenen roten Kristalle mechanisch ab. Ausb.: 1 , l g (66 %) roter Nadeln oder Blattchen vom Schmp. 112-113' (aus Ather odcr Aceton im Kaltebad), die durch weitere Hydrolyse leicht in Thiobenzamid ubergingen. CaH7NOS(165,2) B e r . : C 5 8 , 1 7 , H 4 , 2 8 , N 8 , 4 8 , S 1 9 , 4 1 ; G e f . : C 5 8 , 2 6 , H 4 , 3 4 , N 8 , 4 6 , S 19.34. Dinitrophenylhydrazon 15: Durch Zugabe von 5 ml einer Losung von 1,2 g 2,4-Dinitrophenylhydrazin in 50 ml 30proz. Perchlordure zu 5 ml einer athanol. Losung von 0.82 g 13 und Verdunnen mit Wasser bis zur leichten Triibung. Rote Nadeln vom Schmp. 224O (DioxanlAthanol).Unter der Einwirkung von s-Triazin (1) auf 4-Amino-antipyrin (2) erfolgt durch Aminomethinylierung Bildung des N,N'-Bis-antipyrylformamidins (5). Elektrophiler Eingriff von 1 in die aktive Methylengruppierung von 1,3-Diphenyl-pyrazolon-(5) (6) fuhrt zur Bildung von 1,3-Diphenyl- 4-formimidoyl-pyrazolon-(5) (7) und 4,4'-Methenyl-bis-[ 1,3-diphcnyl-pyrazolon-(5)] (8). Variation of Structure of Analgetics by AminomethinylationUnder the action of s-triazine ( I ) o n 4-amino-antipyrine (2), aminomethinylation results in formation of N,N'-bis-antipyrylformarnidine (5). Electrophilic attack of the active methylene grouping in 1,3-diphcnyl-5-pyrazolone (6) by I leads to the formation of 1,3-diphenyI-4formimidoyl-5-pyrazolone (7) and 4,4'-methenyl-bis-[ 1,3dipheny1-5-pyrazolone] (8).Die Verallgerneinerungsfahigkeit des unter Ringspaltung erfolgenden elektrophilen Eingtiffs des s-Triazins (1) in Arninogruppierungen hat sich in jungerer Zeit an Anthra-

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Die Stoffwechselprodukte des Pyramidons und verwandter Verbindungen beim Menschen

Cited by 46 publications

References 0 publications

Kinetics and metabolism of pyrazolones (propyphenazone, aminopyrine and dipyrone).

Kinetics and metabolism of pyrazolones (propyphenazone, aminopyrine and dipyrone).

References

Strukturabwandlung von Analgetika durch Aminomethinylierung

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