Identification of Mutagenic Nitrosation Products of Antipyrine and Evaluation of Their Formation under Model Stomach Conditions
Nitrosation products of antipyrine treated with nitrite under the conditions recommended by the WHO were examined. An unknown product was confirmed to be formed besides 4-nitrosoantipyrine (a known nitrosation product), and was isolated and identified as 1-(2-hydroxyimino-3-oxobutyryl)-2-methyl-2-ni...
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| Veröffentlicht in: | Chemical & pharmaceutical bulletin 1986/09/25, Vol.34(9), pp.3866-3872 |
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| container_issue | 9 |
| container_start_page | 3866 |
| container_title | Chemical & pharmaceutical bulletin |
| container_volume | 34 |
| creator | OHTA, TAKAFUMI ASABE, YOSHIHIRO TAKITANI, SHOJI |
| description | Nitrosation products of antipyrine treated with nitrite under the conditions recommended by the WHO were examined. An unknown product was confirmed to be formed besides 4-nitrosoantipyrine (a known nitrosation product), and was isolated and identified as 1-(2-hydroxyimino-3-oxobutyryl)-2-methyl-2-nitroso-1-phenylhydrazine.This new nitrosation product showed mutagenicity to Salmonella typhimurium TA 98 and TA 100 either with or without S9 mix. Model experiments indicated that antipyrine is probably easily nitrosated in the stomach after administration to give these nitrosation products. |
| doi_str_mv | 10.1248/cpb.34.3866 |
| format | Article |
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An unknown product was confirmed to be formed besides 4-nitrosoantipyrine (a known nitrosation product), and was isolated and identified as 1-(2-hydroxyimino-3-oxobutyryl)-2-methyl-2-nitroso-1-phenylhydrazine.This new nitrosation product showed mutagenicity to Salmonella typhimurium TA 98 and TA 100 either with or without S9 mix. Model experiments indicated that antipyrine is probably easily nitrosated in the stomach after administration to give these nitrosation products.</description><identifier>ISSN: 0009-2363</identifier><identifier>EISSN: 1347-5223</identifier><identifier>DOI: 10.1248/cpb.34.3866</identifier><identifier>PMID: 3815608</identifier><identifier>CODEN: CPBTAL</identifier><language>eng</language><publisher>Tokyo: The Pharmaceutical Society of Japan</publisher><subject>4-nitroantipyrine ; Antipyrine - analysis ; Antipyrine - toxicity ; Biological and medical sciences ; Drug toxicity and drugs side effects treatment ; Gastric Mucosa - metabolism ; Medical sciences ; Miscellaneous (drug allergy, mutagens, teratogens...) ; Models, Biological ; Mutagens - analysis ; Nitroso Compounds - chemical synthesis ; Pharmacology. 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Pharm. Bull.</addtitle><description>Nitrosation products of antipyrine treated with nitrite under the conditions recommended by the WHO were examined. An unknown product was confirmed to be formed besides 4-nitrosoantipyrine (a known nitrosation product), and was isolated and identified as 1-(2-hydroxyimino-3-oxobutyryl)-2-methyl-2-nitroso-1-phenylhydrazine.This new nitrosation product showed mutagenicity to Salmonella typhimurium TA 98 and TA 100 either with or without S9 mix. Model experiments indicated that antipyrine is probably easily nitrosated in the stomach after administration to give these nitrosation products.</description><subject>4-nitroantipyrine</subject><subject>Antipyrine - analysis</subject><subject>Antipyrine - toxicity</subject><subject>Biological and medical sciences</subject><subject>Drug toxicity and drugs side effects treatment</subject><subject>Gastric Mucosa - metabolism</subject><subject>Medical sciences</subject><subject>Miscellaneous (drug allergy, mutagens, teratogens...)</subject><subject>Models, Biological</subject><subject>Mutagens - analysis</subject><subject>Nitroso Compounds - chemical synthesis</subject><subject>Pharmacology. 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Pharm. Bull.</addtitle><date>1986-09-01</date><risdate>1986</risdate><volume>34</volume><issue>9</issue><spage>3866</spage><epage>3872</epage><pages>3866-3872</pages><issn>0009-2363</issn><eissn>1347-5223</eissn><coden>CPBTAL</coden><abstract>Nitrosation products of antipyrine treated with nitrite under the conditions recommended by the WHO were examined. An unknown product was confirmed to be formed besides 4-nitrosoantipyrine (a known nitrosation product), and was isolated and identified as 1-(2-hydroxyimino-3-oxobutyryl)-2-methyl-2-nitroso-1-phenylhydrazine.This new nitrosation product showed mutagenicity to Salmonella typhimurium TA 98 and TA 100 either with or without S9 mix. 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| identifier | ISSN: 0009-2363 |
| ispartof | Chemical and Pharmaceutical Bulletin, 1986/09/25, Vol.34(9), pp.3866-3872 |
| issn | 0009-2363 1347-5223 |
| language | eng |
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| source | MEDLINE; J-STAGE (Japan Science & Technology Information Aggregator, Electronic) Freely Available Titles - Japanese; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | 4-nitroantipyrine Antipyrine - analysis Antipyrine - toxicity Biological and medical sciences Drug toxicity and drugs side effects treatment Gastric Mucosa - metabolism Medical sciences Miscellaneous (drug allergy, mutagens, teratogens...) Models, Biological Mutagens - analysis Nitroso Compounds - chemical synthesis Pharmacology. Drug treatments |
| title | Identification of Mutagenic Nitrosation Products of Antipyrine and Evaluation of Their Formation under Model Stomach Conditions |
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