Home LiteratureArticle Details
PMID: 522906 Published · ppublish English Journal Article

4,4'-Dihydroxyphenazone as an urinary metabolite of phenazone in different species including man.

Naunyn-Schmiedeberg's archives of pharmacology ·Vol. 309 ·No. 2 ·1979-11-00 ·Pages 203-5

Bässmann H, Böttcher J, Schüppel R

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
Chemicals
Antipyrine
Authors & Affiliations
3 authors, click to expand affiliations / ORCID
Bässmann H
Böttcher J
Schüppel R
References (11)
11 references, click to expand
  1. [Metabolic products of amino-pyrine and related compounds in humans].
    Hoppe Seylers Z Physiol Chem. 1950 Mar;285(1-3):97-127 PMID: 15415037
  2. Norphenazone, a new metabolite of phenazone in human urine.
    J Pharm Pharmacol. 1973 Jan;25(1):83-4 PMID: 4146209
  3. [Demonstration of a new reactive metabolite in metabolism of phenazone (antipyrine)].
    Naunyn Schmiedebergs Arch Exp Pathol Pharmakol. 1968;260(2):219-20 PMID: 4239247
  4. [On the metabolism of antipyrine (phenazone) in man (author's transl)].
    Arzneimittelforschung. 1978;28(2):315-9 PMID: 580401
  5. Metabolism of drugs. LIX. A new metabolite of antipyrine.
    Biochem Pharmacol. 1968 Aug;17(8):1511-6 PMID: 5672814
  6. Metabolism of drugs. LXX. Further study on antipyrine metabolism.
    Chem Pharm Bull (Tokyo). 1971 Jan;19(1):41-5 PMID: 5544367
  7. The fate of antipyrine in man.
    J Pharmacol Exp Ther. 1950 Jan;98(1):97-104 PMID: 15403625
  8. Location of functional groups in antipyrine metabolites by mass spectrometry.
    Biomed Mass Spectrom. 1977 Jun;4(3):155-8 PMID: 890075
  9. 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
  10. 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
  11. Disposition and oxidative metabolism of antipyrine in the rat.
    Acta Pharmacol Toxicol (Copenh). 1978 Jul;43(1):64-8 PMID: 707125
Article Info
Journal
Naunyn-Schmiedeberg's archives of pharmacology
Abbr.
Naunyn Schmiedebergs Arch Pharmacol
ISSN
0028-1298
Published
1979-11-00
Pages
203-5
Language
English
Region
Germany
NLM ID
0326264
Subset
IM
Analysis Services
Analysis Services

Contact

No. 2 Wenbo Road, Zhangqiu District, Jinan, Shandong

Qilu Normal University · Genelibs Bioinformatics Lab

750 Shunhua Rd, Jinan

2F, Bldg F, University Science Park

Tel: 0531-88819269

WeChat Official Account

Follow our WeChat subscription account for real-time updates and the latest in medical and biological research.


Business Email

E-mail: product@genelibs.com