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<h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Gentamicine</span></h1>
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<div id="mw-content-text" class="mw-body-content mw-content-ltr" lang="de" dir="ltr"><div class="mw-content-ltr mw-parser-output" lang="de" dir="ltr"><p>Die <b>Gentamicine</b> sind eine Gruppe von strukturell sehr eng verwandten <a href="Aminoglykosid" class="mw-redirect" title="Aminoglykosid">Aminoglykosidverbindungen</a>. Unter dem <a href="Internationaler_Freiname" title="Internationaler Freiname">Freinamen</a> <i><a href="Gentamicin" title="Gentamicin">Gentamicin</a></i> wird ein <a href="Fermentation" title="Fermentation">fermentativ</a> hergestelltes Typgemisch als <a href="Arzneistoff" title="Arzneistoff">Arzneistoff</a> gegen <a href="Bakterien" title="Bakterien">bakterielle</a> Infektionen eingesetzt.
</p>
<div class="mw-heading mw-heading2"><h2 id="Geschichte">Geschichte</h2></div>
<p>Die ersten Gentamicine wurden im Jahr <a href="1963" title="1963">1963</a> von Mitarbeitern von <a href="Schering-Plough" title="Schering-Plough">Schering</a> in <a href="New_Jersey" title="New Jersey">New Jersey</a> in den Produkten des <a href="Bakterien" title="Bakterien">Bakterienstamms</a> <i>Micromonospora purpurea</i> entdeckt.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Von der bakteriellen Herkunft (M<i>i</i>cromonospora) leitet sich die Schreibweise mit einem „<i>i</i>“ ab. Aminoglykosidantibiotika, die von Streptom<i>y</i>ces-Arten stammen, werden dagegen mit „<i>y</i>“ geschrieben (beispielsweise <a href="Tobramycin" title="Tobramycin">Tobram<i>y</i>cin</a> oder <a href="Streptomycin" title="Streptomycin">Streptom<i>y</i>cin</a>).<sup id="cite_ref-stock_2-0" class="reference"><a href="#cite_note-stock-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup>
</p>
<div class="mw-heading mw-heading2"><h2 id="Strukturen_und_Eigenschaften">Strukturen und Eigenschaften</h2></div>
<p>Die Gentamicine sind aus drei <a href="Hexosamine" title="Hexosamine">Hexosaminen</a> aufgebaut. Es handelt sich hierbei um (siehe Abbildungen, von links nach rechts) Gentosamin/Garosamin, 2-Desoxystreptamin und Purpurosamin.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup>
</p>
<table class="wikitable centered" style="text-align:center; font-size: 100%">
<tbody><tr>
<th class="hintergrundfarbe6" colspan="10">Gentamicine
</th></tr>
<tr>
<th>Name(n)
</th>
<th>Struktur
</th>
<th><a href="CAS-Nummer" title="CAS-Nummer">CAS</a>-<br>Nummer
</th>
<th>PubChem
</th>
<th>Summenformel
</th>
<th>Molare<br>Masse
</th></tr>
<tr>
<td>
<ul><li>Gentamicin A</li></ul>
</td>
<td><span typeof="mw:File"></span>
</td>
<td><span title="Untervorlage eingebunden: CASRN"></span><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=13291-74-2">13291-74-2</a><span class="editoronly" style="display:none;"></span>
</td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/86474">86474</a>
</td>
<td>C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
</td>
<td>468,50 g·mol<sup>−1</sup>
</td></tr>
<tr>
<td>
<ul><li>Gentamicin A<sub>1</sub></li></ul>
</td>
<td><span typeof="mw:File"></span>
</td>
<td>
</td>
<td>
</td>
<td>
</td>
<td>
</td></tr>
<tr>
<td>
<ul><li>Gentamicin A<sub>2</sub></li></ul>
</td>
<td><span typeof="mw:File"></span>
</td>
<td>55715-66-7
</td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/86489">86489</a>
</td>
<td>C<sub>17</sub>H<sub>33</sub>N<sub>3</sub>O<sub>11</sub>
</td>
<td>455,46 g·mol<sup>−1</sup>
</td></tr>
<tr>
<td>
<ul><li>Gentamicin A<sub>3</sub></li></ul>
</td>
<td><span typeof="mw:File"></span>
</td>
<td>55715-67-8
</td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/86490">86490</a>
</td>
<td>C<sub>18</sub>H<sub>36</sub>N<sub>4</sub>O<sub>10</sub>
</td>
<td>468,50 g·mol<sup>−1</sup>
</td></tr>
<tr>
<td>
<ul><li>Gentamicin A<sub>4</sub></li></ul>
</td>
<td><span typeof="mw:File"></span>
</td>
<td>
</td>
<td>
</td>
<td>
</td>
<td>
</td></tr>
<tr>
<td>
<ul><li>Gentamicin B</li>
<li>Betamicin</li></ul>
</td>
<td><span typeof="mw:File"></span>
</td>
<td>36889-15-3
</td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/37569">37569</a>
</td>
<td>C<sub>19</sub>H<sub>38</sub>N<sub>4</sub>O<sub>10</sub>
</td>
<td>482,53 g·mol<sup>−1</sup>
</td></tr>
<tr>
<td>
<ul><li>Gentamicin B<sub>1</sub></li></ul>
</td>
<td><span typeof="mw:File"></span>
</td>
<td>36889-16-4
</td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/3034288">3034288</a>
</td>
<td>C<sub>20</sub>H<sub>40</sub>N<sub>4</sub>O<sub>10</sub>
</td>
<td>496,55 g·mol<sup>−1</sup>
</td></tr>
<tr>
<td>
<ul><li>Gentamicin C<sub>1</sub></li></ul>
</td>
<td><span typeof="mw:File"></span>
</td>
<td>25876-10-2
</td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/441305">441305</a>
</td>
<td>C<sub>21</sub>H<sub>43</sub>N<sub>5</sub>O<sub>7</sub>
</td>
<td>477,59 g·mol<sup>−1</sup>
</td></tr>
<tr>
<td>
<ul><li>Gentamicin C<sub>1a</sub></li></ul>
</td>
<td><span typeof="mw:File"></span>
</td>
<td>26098-04-4
</td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/72396">72396</a>
</td>
<td>C<sub>19</sub>H<sub>39</sub>N<sub>5</sub>O<sub>7</sub>
</td>
<td>449,54 g·mol<sup>−1</sup>
</td></tr>
<tr>
<td>
<ul><li>Gentamicin C<sub>2</sub></li></ul>
</td>
<td><span typeof="mw:File"></span>
</td>
<td>25876-11-3
</td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/72397">72397</a>
</td>
<td>C<sub>20</sub>H<sub>41</sub>N<sub>5</sub>O<sub>7</sub>
</td>
<td>463,57 g·mol<sup>−1</sup>
</td></tr>
<tr>
<td>
<ul><li>Gentamicin C<sub>2a</sub></li></ul>
</td>
<td><span typeof="mw:File"></span>
</td>
<td>59751-72-3
</td>
<td>
</td>
<td>C<sub>20</sub>H<sub>41</sub>N<sub>5</sub>O<sub>7</sub>
</td>
<td>463,57 g·mol<sup>−1</sup>
</td></tr>
<tr>
<td>
<ul><li>Gentamicin C<sub>2b</sub></li>
<li>Micronomicin</li></ul>
</td>
<td><span typeof="mw:File"></span>
</td>
<td>52093-21-7
</td>
<td><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/107677">107677</a>
</td>
<td>C<sub>20</sub>H<sub>41</sub>N<sub>5</sub>O<sub>7</sub>
</td>
<td>463,57 g·mol<sup>−1</sup>
</td></tr>
</tbody></table>
<p>Ähnliche Strukturen weisen auch die <a href="Kanamycine" title="Kanamycine">Kanamycine</a> und <a href="Tobramycin" title="Tobramycin">Tobramycin</a> auf. Bei <a href="Sisomicin" title="Sisomicin">Sisomicin</a> handelt es sich um 4,5-Dehydrogentamicin-C<sub>1a</sub>.
</p><p>Der teilsynthetische Sisomicin-Abkömmling <a href="Plazomicin" title="Plazomicin">Plazomicin</a> wird ebenfalls arzneilich verwendet.
</p>
<div style="clear:both;"></div>
<div class="mw-heading mw-heading2"><h2 id="Einzelnachweise">Einzelnachweise</h2></div>
<ol class="references">
<li id="cite_note-1"><span class="mw-cite-backlink"><a href="#cite_ref-1">↑</a></span> <span class="reference-text"><cite class="lang" lang="en" dir="auto" style="font-style:italic">Gentamicin</cite>. In: <cite class="lang" lang="en" dir="auto" style="font-style:italic">Br Med J</cite>. 1. Jahrgang, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>5533</span>, Januar 1967, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>158–9</span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/6015651?dopt=Abstract">PMID 6015651</a>, <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1840594/">PMC 1840594</a> (freier Volltext) – (englisch).<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Gentamicine&rft.atitle=Gentamicin&rft.date=1967-01&rft.genre=journal&rft.issue=5533&rft.jtitle=Br+Med+J&rft.pages=158-9&rft.pmc=1840594&rft.pmid=6015651&rft.volume=1.+Jahrgang" style="display:none"> </span></span>
</li>
<li id="cite_note-stock-2"><span class="mw-cite-backlink"><a href="#cite_ref-stock_2-0">↑</a></span> <span class="reference-text"><span class="book">Ingo Stock: <cite style="font-style:italic">Bakterien Viren Wirkstoffe</cite>. Govi-Verlag, 2009, ISBN 978-3-7741-1104-2.<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rfr_id=info:sid/de.wikipedia.org:Gentamicine&rft.au=Ingo+Stock&rft.btitle=Bakterien+Viren+Wirkstoffe&rft.date=2009&rft.genre=book&rft.isbn=9783774111042&rft.pub=Govi-Verlag" style="display:none"> </span></span></span>
</li>
<li id="cite_note-3"><span class="mw-cite-backlink"><a href="#cite_ref-3">↑</a></span> <span class="reference-text">Benveniste R, Davies J: <cite class="lang" lang="en" dir="auto" style="font-style:italic">Structure-activity relationships among the aminoglycoside antibiotics: role of hydroxyl and amino groups</cite>. In: <cite class="lang" lang="en" dir="auto" style="font-style:italic">Antimicrob. Agents Chemother.</cite> 4. Jahrgang, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>4</span>, Oktober 1973, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>402–9</span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/4598613?dopt=Abstract">PMID 4598613</a>, <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC444567/">PMC 444567</a> (freier Volltext) – (englisch).<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Gentamicine&rft.atitle=Structure-activity+relationships+among+the+aminoglycoside+antibiotics%3A+role+of+hydroxyl+and+amino+groups&rft.au=Benveniste+R%2C+Davies+J&rft.date=1973-10&rft.genre=journal&rft.issue=4&rft.jtitle=Antimicrob.+Agents+Chemother.&rft.pages=402-9&rft.pmc=444567&rft.pmid=4598613&rft.volume=4.+Jahrgang" style="display:none"> </span></span>
</li>
<li id="cite_note-4"><span class="mw-cite-backlink"><a href="#cite_ref-4">↑</a></span> <span class="reference-text">Vastola AP, Altschaefl J, Harford S: <cite class="lang" lang="en" dir="auto" style="font-style:italic">5-epi-Sisomicin and 5-epi-Gentamicin B: substrates for aminoglycoside-modifying enzymes that retain activity against aminoglycoside-resistant bacteria</cite>. In: <cite class="lang" lang="en" dir="auto" style="font-style:italic">Antimicrob. Agents Chemother.</cite> 17. Jahrgang, <span style="white-space:nowrap">Nr.<span style="display:inline-block;width:.2em"> </span>5</span>, Mai 1980, <span style="white-space:nowrap">S.<span style="display:inline-block;width:.2em"> </span>798–802</span>, <a class="external mw-magiclink-pmid" rel="nofollow" href="https://www.ncbi.nlm.nih.gov/pubmed/6967296?dopt=Abstract">PMID 6967296</a>, <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC283878/">PMC 283878</a> (freier Volltext) – (englisch).<span class="Z3988" title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rfr_id=info:sid/de.wikipedia.org:Gentamicine&rft.atitle=5-epi-Sisomicin+and+5-epi-Gentamicin+B%3A+substrates+for+aminoglycoside-modifying+enzymes+that+retain+activity+against+aminoglycoside-resistant+bacteria&rft.au=Vastola+AP%2C+Altschaefl+J%2C+Harford+S&rft.date=1980-05&rft.genre=journal&rft.issue=5&rft.jtitle=Antimicrob.+Agents+Chemother.&rft.pages=798-802&rft.pmc=283878&rft.pmid=6967296&rft.volume=17.+Jahrgang" style="display:none"> </span></span>
</li>
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