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<meta name="robots" content="INDEX,FOLLOW,NOARCHIVE" /><meta name="citation_inbook_title" content="LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]" /><meta name="citation_title" content="Penicillins (1st Generation)" /><meta name="citation_publisher" content="National Institute of Diabetes and Digestive and Kidney Diseases" /><meta name="citation_date" content="2020/10/20" /><meta name="citation_pmid" content="31644108" /><meta name="citation_fulltext_html_url" content="https://www.ncbi.nlm.nih.gov/books/NBK548801/" /><link rel="schema.DC" href="http://purl.org/DC/elements/1.0/" /><meta name="DC.Title" content="Penicillins (1st Generation)" /><meta name="DC.Type" content="Text" /><meta name="DC.Publisher" content="National Institute of Diabetes and Digestive and Kidney Diseases" /><meta name="DC.Date" content="2020/10/20" /><meta name="DC.Identifier" content="https://www.ncbi.nlm.nih.gov/books/NBK548801/" /><meta name="description" content="The natural or "first generation" penicillins are bactericidal antibiotics naturally derived from the mold, Penicillium chrysogenum. Their basic structure includes a thiazolidine ring connected to a beta-lactam ring with a variable side chain. Penicillins bind to bacterial proteins and inhibit synthesis of the bacterial cell wall, causing cell lysis particularly in rapidly growing organisms. Bacterial resistance to penicillin is usually mediated by beta-lactamase, an enzyme which destroys the beta-lactam ring of penicillin, rendering it inactive. Penicillin was introduced into medicine in the 1940’s and ushered in the modern era of antibiotic therapy, ending the dominance of many diseases that had been major causes of morbidity and mortality. At present, several first generation penicillins are available in the United States: the benzathine, potassium, procaine and sodium salts of penicillin G and the orally available penicillin V potassium. These agents are discussed together as they are rare causes of hepatotoxicity and can be considered similar enough to be grouped together." /><meta name="og:title" content="Penicillins (1st Generation)" /><meta name="og:type" content="book" /><meta name="og:description" content="The natural or "first generation" penicillins are bactericidal antibiotics naturally derived from the mold, Penicillium chrysogenum. Their basic structure includes a thiazolidine ring connected to a beta-lactam ring with a variable side chain. Penicillins bind to bacterial proteins and inhibit synthesis of the bacterial cell wall, causing cell lysis particularly in rapidly growing organisms. Bacterial resistance to penicillin is usually mediated by beta-lactamase, an enzyme which destroys the beta-lactam ring of penicillin, rendering it inactive. Penicillin was introduced into medicine in the 1940’s and ushered in the modern era of antibiotic therapy, ending the dominance of many diseases that had been major causes of morbidity and mortality. At present, several first generation penicillins are available in the United States: the benzathine, potassium, procaine and sodium salts of penicillin G and the orally available penicillin V potassium. These agents are discussed together as they are rare causes of hepatotoxicity and can be considered similar enough to be grouped together." /><meta name="og:url" content="https://www.ncbi.nlm.nih.gov/books/NBK548801/" /><meta name="og:site_name" content="NCBI Bookshelf" /><meta name="og:image" content="https://www.ncbi.nlm.nih.gov/corehtml/pmc/pmcgifs/bookshelf/thumbs/th-livertox-lrg.png" /><meta name="twitter:card" content="summary" /><meta name="twitter:site" content="@ncbibooks" /><meta name="bk-non-canon-loc" content="/books/n/livertox/PenicillinFirstGen/" /><link rel="canonical" href="https://www.ncbi.nlm.nih.gov/books/NBK548801/" /><link rel="stylesheet" href="/corehtml/pmc/css/figpopup.css" type="text/css" media="screen" /><link rel="stylesheet" href="/corehtml/pmc/css/bookshelf/2.26/css/books.min.css" type="text/css" /><link rel="stylesheet" href="/corehtml/pmc/css/bookshelf/2.26/css/books_print.min.css" type="text/css" /><style type="text/css">p a.figpopup{display:inline !important} .bk_tt {font-family: monospace} .first-line-outdent .bk_ref {display: inline} </style><script type="text/javascript" src="/corehtml/pmc/js/jquery.hoverIntent.min.js"> </script><script type="text/javascript" src="/corehtml/pmc/js/common.min.js?_=3.18"> </script><script type="text/javascript">window.name="mainwindow";</script><script type="text/javascript" src="/corehtml/pmc/js/bookshelf/2.26/book-toc.min.js"> </script><script type="text/javascript" src="/corehtml/pmc/js/bookshelf/2.26/books.min.js"> </script>
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<div class="pre-content"><div><div class="bk_prnt"><p class="small">NCBI Bookshelf. A service of the National Library of Medicine, National Institutes of Health.</p><p>LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. </p></div></div></div>
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<div class="main-content lit-style" itemscope="itemscope" itemtype="http://schema.org/CreativeWork"><div class="meta-content fm-sec"><h1 id="_NBK548801_"><span class="title" itemprop="name">Penicillins (1st Generation)</span></h1><p class="small">Last Update: <span itemprop="dateModified">October 20, 2020</span>.</p></div><div class="body-content whole_rhythm" itemprop="text"><div id="PenicillinFirstGen.OVERVIEW"><h2 id="_PenicillinFirstGen_OVERVIEW_">OVERVIEW</h2><p>The natural or "first generation" penicillins are bactericidal antibiotics naturally derived from the mold, Penicillium chrysogenum. Their basic structure includes a thiazolidine ring connected to a beta-lactam ring with a variable side chain. Penicillins bind to bacterial proteins and inhibit synthesis of the bacterial cell wall, causing cell lysis particularly in rapidly growing organisms. Bacterial resistance to penicillin is usually mediated by beta-lactamase, an enzyme which destroys the beta-lactam ring of penicillin, rendering it inactive. Penicillin was introduced into medicine in the 1940’s and ushered in the modern era of antibiotic therapy, ending the dominance of many diseases that had been major causes of morbidity and mortality. At present, several first generation penicillins are available in the United States: the benzathine, potassium, procaine and sodium salts of penicillin G and the orally available penicillin V potassium. These agents are discussed together as they are rare causes of hepatotoxicity and can be considered similar enough to be grouped together.</p><p>Drug Class: <a href="/books/n/livertox/Antiinfective/">Antiinfective Agents</a></p><p>The following are links to each drug record:</p><ul><li class="half_rhythm"><div>
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||
<a href="/books/n/livertox/PenicilllinGandV/">Penicillin G</a>
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||
</div></li><li class="half_rhythm"><div>
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||
<a href="/books/n/livertox/PenicilllinGandV/">Penicillin G Benzathine</a>
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||
</div></li><li class="half_rhythm"><div>
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||
<a href="/books/n/livertox/PenicilllinGandV/">Penicillin V</a>
|
||
</div></li></ul></div><div id="PenicillinFirstGen.CHEMICAL_FORMULAS_AND"><h2 id="_PenicillinFirstGen_CHEMICAL_FORMULAS_AND_">CHEMICAL FORMULAS AND STRUCTURES</h2><div id="PenicillinFirstGen.Tc" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK548801/table/PenicillinFirstGen.Tc/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__PenicillinFirstGen.Tc_lrgtbl__"><table><thead><tr><th id="hd_h_PenicillinFirstGen.Tc_1_1_1_1" scope="col" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">DRUG</th><th id="hd_h_PenicillinFirstGen.Tc_1_1_1_2" scope="col" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">CAS REGISTRY NO</th><th id="hd_h_PenicillinFirstGen.Tc_1_1_1_3" scope="col" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">MOLECULAR FORMULA</th><th id="hd_h_PenicillinFirstGen.Tc_1_1_1_4" scope="col" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">STRUCTURE</th></tr></thead><tbody><tr><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_1" scope="row" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Penicillin G<br /> (Benzylpenicillin)</td><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_2" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
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||
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/134971028" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem">61-33-6</a>
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||
</td><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_3" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">C16-H18-N2-O4-S</td><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_4" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
|
||
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/134971028" title="View this structure in PubChem" class="img_link" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem"><img src="https://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?t=l&sid=134971028" alt="image 134971028 in the ncbi pubchem database" /></a>
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||
</td></tr><tr><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_1" scope="row" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Penicillin G<br /> Sodium</td><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_2" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
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||
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/134971671" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem">69-57-8</a>
|
||
</td><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_3" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">C16-H18-N2-O4-S</td><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_4" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
|
||
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/134971671" title="View this structure in PubChem" class="img_link" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem"><img src="https://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?t=l&sid=134971671" alt="image 134971671 in the ncbi pubchem database" /></a>
|
||
</td></tr><tr><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_1" scope="row" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Penicillin G<br /> Potassium</td><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_2" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
|
||
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/134974188" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem">113-98-4</a>
|
||
</td><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_3" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">C16-H18-N2-O4-S.K</td><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_4" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
|
||
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/134974188" title="View this structure in PubChem" class="img_link" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem"><img src="https://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?t=l&sid=134974188" alt="image 134974188 in the ncbi pubchem database" /></a>
|
||
</td></tr><tr><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_1" scope="row" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Penicillin V</td><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_2" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
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||
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/134971429" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem">87-08-1</a>
|
||
</td><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_3" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">C16-H18-N2-O5-S</td><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_4" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
|
||
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/134971429" title="View this structure in PubChem" class="img_link" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem"><img src="https://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?t=l&sid=134971429" alt="image 134971429 in the ncbi pubchem database" /></a>
|
||
</td></tr><tr><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_1" scope="row" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Penicillin V<br /> Potassium</td><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_2" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
|
||
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/134974408" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem">132-98-9</a>
|
||
</td><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_3" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">C16-H17-K-N2-O5-S<br /> C16-H17-N2-O5-S.K<br /> C16-H18-N2-O5-S.K</td><td headers="hd_h_PenicillinFirstGen.Tc_1_1_1_4" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
|
||
<a href="https://pubchem.ncbi.nlm.nih.gov/substance/134974408" title="View this structure in PubChem" class="img_link" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem"><img src="https://pubchem.ncbi.nlm.nih.gov/image/imgsrv.fcgi?t=l&sid=134974408" alt="image 134974408 in the ncbi pubchem database" /></a>
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</td></tr></tbody></table></div></div></div><div id="bk_toc_contnr"></div></div></div>
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