Species Differences in the Biotransformation of 4-(2-Methyl-3-(4-chlorobenzoyl)phenyl)butanoic Acid (RU16029)
1. 4-(2-Methyl-3-(4-chlorobenzoyl)phenyl)butanoic acid (RU 16029) is a potent anti-inflammatory and analgesic agent. In humans, its ketone group is rapidly reduced to an alcohol, whereas in rats, mice and dogs, its butanoic sidechain is rapidly oxidized to the corresponding acetic acid. 2. The exten...
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| Veröffentlicht in: | Xenobiotica 1978-01, Vol.8 (7), p.429-437 |
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| creator | Pottier, J. Busigny, M. Raynaud, J. P. |
| description | 1. 4-(2-Methyl-3-(4-chlorobenzoyl)phenyl)butanoic acid (RU 16029) is a potent anti-inflammatory and analgesic agent. In humans, its ketone group is rapidly reduced to an alcohol, whereas in rats, mice and dogs, its butanoic sidechain is rapidly oxidized to the corresponding acetic acid.
2. The extent of this oxidation was studied in eleven species. Cats, dogs, rabbits, hens and rodents readily oxidized the side-chain; humans, baboons and pigs showed only weak oxidizing capacity.
3. Species differences were also recorded in the secondary biotransformations. The acetic metabolite is excreted as an acylglucuronide in humans and rats, but as an amide-like conjugate in mice.
4. Comparison with biotransformations undergone by structurally related compounds confirms that the metabolism of a new compound in different species is unpredictable. |
| doi_str_mv | 10.3109/00498257809070027 |
| format | Article |
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2. The extent of this oxidation was studied in eleven species. Cats, dogs, rabbits, hens and rodents readily oxidized the side-chain; humans, baboons and pigs showed only weak oxidizing capacity.
3. Species differences were also recorded in the secondary biotransformations. The acetic metabolite is excreted as an acylglucuronide in humans and rats, but as an amide-like conjugate in mice.
4. Comparison with biotransformations undergone by structurally related compounds confirms that the metabolism of a new compound in different species is unpredictable.</description><identifier>ISSN: 0049-8254</identifier><identifier>EISSN: 1366-5928</identifier><identifier>DOI: 10.3109/00498257809070027</identifier><identifier>PMID: 98921</identifier><language>eng</language><publisher>England: Informa UK Ltd</publisher><subject>Animals ; Anti-Inflammatory Agents, Non-Steroidal - metabolism ; Biotransformation ; Cats ; Chickens ; Cricetinae ; Dogs ; Female ; Haplorhini ; Humans ; Hydrolysis ; Kinetics ; Male ; Mesocricetus ; Mice ; Oxidation-Reduction ; Papio ; Phenylbutyrates - metabolism ; Rabbits ; Rats ; Species Specificity ; Swine ; Time Factors</subject><ispartof>Xenobiotica, 1978-01, Vol.8 (7), p.429-437</ispartof><rights>1978 Informa UK Ltd All rights reserved: reproduction in whole or part not permitted 1978</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c399t-84aa024a9fdb0d6d3f15976c1affeb03fd5154bc2079da897d87a794709f323f3</citedby><cites>FETCH-LOGICAL-c399t-84aa024a9fdb0d6d3f15976c1affeb03fd5154bc2079da897d87a794709f323f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.3109/00498257809070027$$EPDF$$P50$$Ginformahealthcare$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.3109/00498257809070027$$EHTML$$P50$$Ginformahealthcare$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,59620,59726,60409,60515,61194,61229,61375,61410</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/98921$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pottier, J.</creatorcontrib><creatorcontrib>Busigny, M.</creatorcontrib><creatorcontrib>Raynaud, J. P.</creatorcontrib><title>Species Differences in the Biotransformation of 4-(2-Methyl-3-(4-chlorobenzoyl)phenyl)butanoic Acid (RU16029)</title><title>Xenobiotica</title><addtitle>Xenobiotica</addtitle><description>1. 4-(2-Methyl-3-(4-chlorobenzoyl)phenyl)butanoic acid (RU 16029) is a potent anti-inflammatory and analgesic agent. In humans, its ketone group is rapidly reduced to an alcohol, whereas in rats, mice and dogs, its butanoic sidechain is rapidly oxidized to the corresponding acetic acid.
2. The extent of this oxidation was studied in eleven species. Cats, dogs, rabbits, hens and rodents readily oxidized the side-chain; humans, baboons and pigs showed only weak oxidizing capacity.
3. Species differences were also recorded in the secondary biotransformations. The acetic metabolite is excreted as an acylglucuronide in humans and rats, but as an amide-like conjugate in mice.
4. Comparison with biotransformations undergone by structurally related compounds confirms that the metabolism of a new compound in different species is unpredictable.</description><subject>Animals</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - metabolism</subject><subject>Biotransformation</subject><subject>Cats</subject><subject>Chickens</subject><subject>Cricetinae</subject><subject>Dogs</subject><subject>Female</subject><subject>Haplorhini</subject><subject>Humans</subject><subject>Hydrolysis</subject><subject>Kinetics</subject><subject>Male</subject><subject>Mesocricetus</subject><subject>Mice</subject><subject>Oxidation-Reduction</subject><subject>Papio</subject><subject>Phenylbutyrates - metabolism</subject><subject>Rabbits</subject><subject>Rats</subject><subject>Species Specificity</subject><subject>Swine</subject><subject>Time Factors</subject><issn>0049-8254</issn><issn>1366-5928</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1978</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMuKFDEUhoM4aDv6AOKmVtKziJ5cqlJBN-N4hRFBnXWRyoXKUJX0JCmkfXrT04Mgoqv_wH_h8CH0lMALRkC-BOCyp63oQYIAoOIe2hDWdbiVtL-PNgcf1wB_iB7lfA0AHaH0ATqRvaRkg5ZvO6u9zc1b75xNNuh6-9CUyTZvfCxJhexiWlTxMTTRNRxvKf5sy7SfMcNbjvU0xxRHG37G_Xy2m2yoMq5Fheh1c669abZfr0gHVJ49RidOzdk-udNTdPX-3feLj_jyy4dPF-eXWDMpC-65UkC5ks6MYDrDHGml6DRR9ccRmDMtafmoKQhpVC-F6YUSkguQjlHm2Cl6ftzdpXiz2lyGxWdt51kFG9c8CE4oI72sQXIM6hRzTtYNu-QXlfYDgeEAePgLcO08uxtfx8Wa341botV9fXR9uOX2I6bZDEXtKyVXaWqfD8P_Hn_1R32yai6TVskO13FNoVL7z2u_AKhEmYc</recordid><startdate>19780101</startdate><enddate>19780101</enddate><creator>Pottier, J.</creator><creator>Busigny, M.</creator><creator>Raynaud, J. P.</creator><general>Informa UK Ltd</general><general>Taylor & Francis</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>19780101</creationdate><title>Species Differences in the Biotransformation of 4-(2-Methyl-3-(4-chlorobenzoyl)phenyl)butanoic Acid (RU16029)</title><author>Pottier, J. ; Busigny, M. ; Raynaud, J. P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c399t-84aa024a9fdb0d6d3f15976c1affeb03fd5154bc2079da897d87a794709f323f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1978</creationdate><topic>Animals</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - metabolism</topic><topic>Biotransformation</topic><topic>Cats</topic><topic>Chickens</topic><topic>Cricetinae</topic><topic>Dogs</topic><topic>Female</topic><topic>Haplorhini</topic><topic>Humans</topic><topic>Hydrolysis</topic><topic>Kinetics</topic><topic>Male</topic><topic>Mesocricetus</topic><topic>Mice</topic><topic>Oxidation-Reduction</topic><topic>Papio</topic><topic>Phenylbutyrates - metabolism</topic><topic>Rabbits</topic><topic>Rats</topic><topic>Species Specificity</topic><topic>Swine</topic><topic>Time Factors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pottier, J.</creatorcontrib><creatorcontrib>Busigny, M.</creatorcontrib><creatorcontrib>Raynaud, J. P.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Xenobiotica</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pottier, J.</au><au>Busigny, M.</au><au>Raynaud, J. P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Species Differences in the Biotransformation of 4-(2-Methyl-3-(4-chlorobenzoyl)phenyl)butanoic Acid (RU16029)</atitle><jtitle>Xenobiotica</jtitle><addtitle>Xenobiotica</addtitle><date>1978-01-01</date><risdate>1978</risdate><volume>8</volume><issue>7</issue><spage>429</spage><epage>437</epage><pages>429-437</pages><issn>0049-8254</issn><eissn>1366-5928</eissn><abstract>1. 4-(2-Methyl-3-(4-chlorobenzoyl)phenyl)butanoic acid (RU 16029) is a potent anti-inflammatory and analgesic agent. In humans, its ketone group is rapidly reduced to an alcohol, whereas in rats, mice and dogs, its butanoic sidechain is rapidly oxidized to the corresponding acetic acid.
2. The extent of this oxidation was studied in eleven species. Cats, dogs, rabbits, hens and rodents readily oxidized the side-chain; humans, baboons and pigs showed only weak oxidizing capacity.
3. Species differences were also recorded in the secondary biotransformations. The acetic metabolite is excreted as an acylglucuronide in humans and rats, but as an amide-like conjugate in mice.
4. Comparison with biotransformations undergone by structurally related compounds confirms that the metabolism of a new compound in different species is unpredictable.</abstract><cop>England</cop><pub>Informa UK Ltd</pub><pmid>98921</pmid><doi>10.3109/00498257809070027</doi><tpages>9</tpages></addata></record> |
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| ispartof | Xenobiotica, 1978-01, Vol.8 (7), p.429-437 |
| issn | 0049-8254 1366-5928 |
| language | eng |
| recordid | cdi_pubmed_primary_98921 |
| source | Taylor & Francis Online; MEDLINE; Taylor & Francis Medical Library - CRKN |
| subjects | Animals Anti-Inflammatory Agents, Non-Steroidal - metabolism Biotransformation Cats Chickens Cricetinae Dogs Female Haplorhini Humans Hydrolysis Kinetics Male Mesocricetus Mice Oxidation-Reduction Papio Phenylbutyrates - metabolism Rabbits Rats Species Specificity Swine Time Factors |
| title | Species Differences in the Biotransformation of 4-(2-Methyl-3-(4-chlorobenzoyl)phenyl)butanoic Acid (RU16029) |
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