Abstract
4,4'-Dihydroxyphenazone (4-hydroxy-1-4'-hydroxyphenyl)-2,3-dimethyl-3-pyrazoline-5-one) was isolated as a metabolite of phenazone (antipyrine) after acid hydrolysis of rat urine. This was characterized and identified by NMR, MS, IR, UV, Fp and epsilon270. After dosage with phenazone, 4,4'-dihydroxyphenazone is excreted in conjugated form by man, rabbit, guinea pig and rat. In the rat it is further shown, that conjugates of 4,4'-dihydroxyphenazone are formed by glucuronidation as well as by sulfatation. The metabolite seems to add substantially to the overall metabolic pattern of phenazone in these species.
MeSH Terms
Animals
Antipyrine/metabolism,urine
Guinea Pigs
Humans
Hydroxylation
Male
Rabbits
Rats
Species Specificity
Authors & Affiliations
3 authors, click to expand affiliations / ORCID
Bässmann H
Böttcher J
Schüppel R
References (11)
11 references, click to expand
-
[Metabolic products of amino-pyrine and related compounds in humans].
Hoppe Seylers Z Physiol Chem. 1950 Mar;285(1-3):97-127
PMID: 15415037
-
Norphenazone, a new metabolite of phenazone in human urine.
J Pharm Pharmacol. 1973 Jan;25(1):83-4
PMID: 4146209
-
[Demonstration of a new reactive metabolite in metabolism of phenazone (antipyrine)].
Naunyn Schmiedebergs Arch Exp Pathol Pharmakol. 1968;260(2):219-20
PMID: 4239247
-
[On the metabolism of antipyrine (phenazone) in man (author's transl)].
Arzneimittelforschung. 1978;28(2):315-9
PMID: 580401
-
Metabolism of drugs. LIX. A new metabolite of antipyrine.
Biochem Pharmacol. 1968 Aug;17(8):1511-6
PMID: 5672814
-
Metabolism of drugs. LXX. Further study on antipyrine metabolism.
Chem Pharm Bull (Tokyo). 1971 Jan;19(1):41-5
PMID: 5544367
-
The fate of antipyrine in man.
J Pharmacol Exp Ther. 1950 Jan;98(1):97-104
PMID: 15403625
-
Location of functional groups in antipyrine metabolites by mass spectrometry.
Biomed Mass Spectrom. 1977 Jun;4(3):155-8
PMID: 890075
-
Metabolism of antipyrine by the epoxide-diol pathway in the rat, guinea pig and human.
Res Commun Chem Pathol Pharmacol. 1974 Aug;8(4):593-606
PMID: 4418208
-
Quantitation of N-demethylantipyrine in biological samples and isolation and characterization of its glucuronic acid conjugate.
Drug Metab Dispos. 1978 May-Jun;6(3):288-95
PMID: 26550
-
Disposition and oxidative metabolism of antipyrine in the rat.
Acta Pharmacol Toxicol (Copenh). 1978 Jul;43(1):64-8
PMID: 707125