Pharmacokinetic interactions related to the chemical structures of fluoroquinolones
Identifieur interne : 002A58 ( Istex/Corpus ); précédent : 002A57; suivant : 002A59Pharmacokinetic interactions related to the chemical structures of fluoroquinolones
Auteurs : Yasuyuki Mizuki ; Iwao Fujiwara ; Toshikazu YamaguchiSource :
- Journal of Antimicrobial Chemotherapy [ 0305-7453 ] ; 1996-05.
Abstract
Fluoroquinolone derivatives interact with methylxanthines (theophylline, caffeine) and metallic ion-containing drugs to different degrees. The rat appears to be a suitable model for predicting such interactions in man. It has been possible to determine the relationship between the chemical structure of the fluoroquinolone and the magnitude of the interaction. Fluoroquinolones with a bulky substituent at the position 8, such as sparfloxacin, lomefloxacin and fleroxacin, are less prone to interact with theophylline than those without an 8-substituent, such as enoxacin. This substituent determines the planarity of the whole fluoroquinolone molecule and the interaction tends to be more significant for planar fluoroquinolones. Furthermore, a 4′-nitrogen atom in the 7-piperazinyl group is essential for the interaction to occur. The nitrogen atom is possibly the site that binds cytochrome P-450, which catalyses theophylline metabolism. The reduction in bioavailability of fluoroquinolones by concurrent administration of aluminium hydroxide is more striking for derivatives with fewer substituents on the essential structure and on the piperazinyl group, such as norfloxacin, ciprofloxacin and enoxacin. Substitution at the 5-position diminishes the interaction, which suggests that the 5-substituent may affect the formation and/or stability of unabsorbable chelate complex which is the probable cause of the interaction. These findings are potentially useful in designing fluoroquinolones less prone to drug interactions.
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DOI: 10.1093/jac/37.suppl_A.41
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<record><TEI wicri:istexFullTextTei="biblStruct"><teiHeader><fileDesc><titleStmt><title>Pharmacokinetic interactions related to the chemical structures of fluoroquinolones</title><author><name sortKey="Mizuki, Yasuyuki" sort="Mizuki, Yasuyuki" uniqKey="Mizuki Y" first="Yasuyuki" last="Mizuki">Yasuyuki Mizuki</name><affiliation><mods:affiliation>Department of Pharmacokinetics, Developmental Research Laboratories, Dainippon Pharmaceutical Co., Ltd, Enoki-cho 33–94, Suita, Osaka 564, Japan</mods:affiliation></affiliation></author><author><name sortKey="Fujiwara, Iwao" sort="Fujiwara, Iwao" uniqKey="Fujiwara I" first="Iwao" last="Fujiwara">Iwao Fujiwara</name><affiliation><mods:affiliation>Department of Pharmacokinetics, Developmental Research Laboratories, Dainippon Pharmaceutical Co., Ltd, Enoki-cho 33–94, Suita, Osaka 564, Japan</mods:affiliation></affiliation></author><author><name sortKey="Yamaguchi, Toshikazu" sort="Yamaguchi, Toshikazu" uniqKey="Yamaguchi T" first="Toshikazu" last="Yamaguchi">Toshikazu Yamaguchi</name><affiliation><mods:affiliation>Department of Pharmacokinetics, Developmental Research Laboratories, Dainippon Pharmaceutical Co., Ltd, Enoki-cho 33–94, Suita, Osaka 564, Japan</mods:affiliation></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:AC78E742B0BFBA9EFBB91523680196636B7C1B4F</idno><date when="1996" year="1996">1996</date><idno type="doi">10.1093/jac/37.suppl_A.41</idno><idno type="url">https://api.istex.fr/document/AC78E742B0BFBA9EFBB91523680196636B7C1B4F/fulltext/pdf</idno><idno type="wicri:Area/Istex/Corpus">002A58</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a">Pharmacokinetic interactions related to the chemical structures of fluoroquinolones</title><author><name sortKey="Mizuki, Yasuyuki" sort="Mizuki, Yasuyuki" uniqKey="Mizuki Y" first="Yasuyuki" last="Mizuki">Yasuyuki Mizuki</name><affiliation><mods:affiliation>Department of Pharmacokinetics, Developmental Research Laboratories, Dainippon Pharmaceutical Co., Ltd, Enoki-cho 33–94, Suita, Osaka 564, Japan</mods:affiliation></affiliation></author><author><name sortKey="Fujiwara, Iwao" sort="Fujiwara, Iwao" uniqKey="Fujiwara I" first="Iwao" last="Fujiwara">Iwao Fujiwara</name><affiliation><mods:affiliation>Department of Pharmacokinetics, Developmental Research Laboratories, Dainippon Pharmaceutical Co., Ltd, Enoki-cho 33–94, Suita, Osaka 564, Japan</mods:affiliation></affiliation></author><author><name sortKey="Yamaguchi, Toshikazu" sort="Yamaguchi, Toshikazu" uniqKey="Yamaguchi T" first="Toshikazu" last="Yamaguchi">Toshikazu Yamaguchi</name><affiliation><mods:affiliation>Department of Pharmacokinetics, Developmental Research Laboratories, Dainippon Pharmaceutical Co., Ltd, Enoki-cho 33–94, Suita, Osaka 564, Japan</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j">Journal of Antimicrobial Chemotherapy</title><idno type="ISSN">0305-7453</idno><idno type="eISSN">1460-2091</idno><imprint><publisher>Oxford University Press</publisher><date type="published" when="1996-05">1996-05</date><biblScope unit="volume">37</biblScope><biblScope unit="supplement">suppl_A</biblScope><biblScope unit="page" from="41">41</biblScope><biblScope unit="page" to="55">55</biblScope></imprint><idno type="ISSN">0305-7453</idno></series><idno type="istex">AC78E742B0BFBA9EFBB91523680196636B7C1B4F</idno><idno type="DOI">10.1093/jac/37.suppl_A.41</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0305-7453</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract">Fluoroquinolone derivatives interact with methylxanthines (theophylline, caffeine) and metallic ion-containing drugs to different degrees. The rat appears to be a suitable model for predicting such interactions in man. It has been possible to determine the relationship between the chemical structure of the fluoroquinolone and the magnitude of the interaction. Fluoroquinolones with a bulky substituent at the position 8, such as sparfloxacin, lomefloxacin and fleroxacin, are less prone to interact with theophylline than those without an 8-substituent, such as enoxacin. This substituent determines the planarity of the whole fluoroquinolone molecule and the interaction tends to be more significant for planar fluoroquinolones. Furthermore, a 4′-nitrogen atom in the 7-piperazinyl group is essential for the interaction to occur. The nitrogen atom is possibly the site that binds cytochrome P-450, which catalyses theophylline metabolism. The reduction in bioavailability of fluoroquinolones by concurrent administration of aluminium hydroxide is more striking for derivatives with fewer substituents on the essential structure and on the piperazinyl group, such as norfloxacin, ciprofloxacin and enoxacin. Substitution at the 5-position diminishes the interaction, which suggests that the 5-substituent may affect the formation and/or stability of unabsorbable chelate complex which is the probable cause of the interaction. These findings are potentially useful in designing fluoroquinolones less prone to drug interactions.</div></front></TEI><istex><corpusName>oup</corpusName><author><json:item><name>Yasuyuki Mizuki</name><affiliations><json:string>Department of Pharmacokinetics, Developmental Research Laboratories, Dainippon Pharmaceutical Co., Ltd, Enoki-cho 33–94, Suita, Osaka 564, Japan</json:string></affiliations></json:item><json:item><name>Iwao Fujiwara</name><affiliations><json:string>Department of Pharmacokinetics, Developmental Research Laboratories, Dainippon Pharmaceutical Co., Ltd, Enoki-cho 33–94, Suita, Osaka 564, Japan</json:string></affiliations></json:item><json:item><name>Toshikazu Yamaguchi</name><affiliations><json:string>Department of Pharmacokinetics, Developmental Research Laboratories, Dainippon Pharmaceutical Co., Ltd, Enoki-cho 33–94, Suita, Osaka 564, Japan</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>Articles</value></json:item></subject><language><json:string>eng</json:string></language><abstract>Fluoroquinolone derivatives interact with methylxanthines (theophylline, caffeine) and metallic ion-containing drugs to different degrees. The rat appears to be a suitable model for predicting such interactions in man. It has been possible to determine the relationship between the chemical structure of the fluoroquinolone and the magnitude of the interaction. Fluoroquinolones with a bulky substituent at the position 8, such as sparfloxacin, lomefloxacin and fleroxacin, are less prone to interact with theophylline than those without an 8-substituent, such as enoxacin. This substituent determines the planarity of the whole fluoroquinolone molecule and the interaction tends to be more significant for planar fluoroquinolones. Furthermore, a 4′-nitrogen atom in the 7-piperazinyl group is essential for the interaction to occur. The nitrogen atom is possibly the site that binds cytochrome P-450, which catalyses theophylline metabolism. The reduction in bioavailability of fluoroquinolones by concurrent administration of aluminium hydroxide is more striking for derivatives with fewer substituents on the essential structure and on the piperazinyl group, such as norfloxacin, ciprofloxacin and enoxacin. Substitution at the 5-position diminishes the interaction, which suggests that the 5-substituent may affect the formation and/or stability of unabsorbable chelate complex which is the probable cause of the interaction. 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The reduction in bioavailability of fluoroquinolones by concurrent administration of aluminium hydroxide is more striking for derivatives with fewer substituents on the essential structure and on the piperazinyl group, such as norfloxacin, ciprofloxacin and enoxacin. Substitution at the 5-position diminishes the interaction, which suggests that the 5-substituent may affect the formation and/or stability of unabsorbable chelate complex which is the probable cause of the interaction. 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The rat appears to be a suitable model for predicting such interactions in man. It has been possible to determine the relationship between the chemical structure of the fluoroquinolone and the magnitude of the interaction. Fluoroquinolones with a bulky substituent at the position 8, such as sparfloxacin, lomefloxacin and fleroxacin, are less prone to interact with theophylline than those without an 8-substituent, such as enoxacin. This substituent determines the planarity of the whole fluoroquinolone molecule and the interaction tends to be more significant for planar fluoroquinolones. Furthermore, a 4′-nitrogen atom in the 7-piperazinyl group is essential for the interaction to occur. The nitrogen atom is possibly the site that binds cytochrome P-450, which catalyses theophylline metabolism. The reduction in bioavailability of fluoroquinolones by concurrent administration of aluminium hydroxide is more striking for derivatives with fewer substituents on the essential structure and on the piperazinyl group, such as norfloxacin, ciprofloxacin and enoxacin. Substitution at the 5-position diminishes the interaction, which suggests that the 5-substituent may affect the formation and/or stability of unabsorbable chelate complex which is the probable cause of the interaction. 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The reduction in bioavailability of fluoroquinolones by concurrent administration of aluminium hydroxide is more striking for derivatives with fewer substituents on the essential structure and on the piperazinyl group, such as norfloxacin, ciprofloxacin and enoxacin. Substitution at the 5-position diminishes the interaction, which suggests that the 5-substituent may affect the formation and/or stability of unabsorbable chelate complex which is the probable cause of the interaction. 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