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<script type="text/javascript" src="/corehtml/pmc/jatsreader/ptpmc_3.22/js/jr.boots.min.js"> </script><title>Estazolam - LiverTox - NCBI Bookshelf</title>
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<meta name="citation_inbook_title" content="LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]">
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<meta name="citation_title" content="Estazolam">
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<meta name="citation_publisher" content="National Institute of Diabetes and Digestive and Kidney Diseases">
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<meta name="citation_date" content="2023/06/22">
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yet</button><a id="jr-fip-next" class="wsprkl btn" title="Jump to next match">▶</a></nav></nav></div><div id="jr-epub-interstitial" class="hidden"></div><div id="jr-content"><article data-type="main"><div class="main-content lit-style" itemscope="itemscope" itemtype="http://schema.org/CreativeWork"><div class="meta-content fm-sec"><div class="fm-sec"><h1 id="_NBK548660_"><span class="title" itemprop="name">Estazolam</span></h1><p class="fm-aai"><a href="#_NBK548660_pubdet_">Publication Details</a></p></div></div><div class="body-content whole_rhythm" itemprop="text"><div id="Estazolam.OVERVIEW"><h2 id="_Estazolam_OVERVIEW_">OVERVIEW</h2><div id="Estazolam.Introduction"><h3>Introduction</h3><p>Estazolam is an orally available benzodiazepine used to treat insomnia. As with most benzodiazepines, estazolam has not been associated with serum aminotransferase or alkaline phosphatase elevations during therapy, and clinically apparent liver injury from estazolam has not been reported and must be very rare, if it occurs at all.</p></div><div id="Estazolam.Background"><h3>Background</h3><p>Estazolam (es taz' oh lam) is a benzodiazepine used as a sleeping aid in the therapy of insomnia. The antianxiety (anxiolytic) and soporific activity of the benzodiazepines is mediated by their ability to enhance gamma-aminobutyric acid (GABA) mediated inhibition of synaptic transmission through binding to the GABA A receptor. Estazolam was approved in the United States in 1990 for the short term management of insomnia and is now rarely used, having been replaced by more effective and better tolerated agents. Estazolam is available in tablets of 1 and 2 mg in several generic forms and formerly under the brand name ProSom. The recommended initial oral dose for adults is 1 mg at bedtime, which can be increased to 2 mg nightly, but is not recommended as chronic therapy. The most common side effects of estazolam are dose related and include daytime drowsiness, lethargy, ataxia, dysarthria and dizziness. Tolerance develops to these side effects, but tolerance may also develop to the effects on insomnia. Estazolam like all oral benzodiazepines has a boxed warning in its product label stressing (1) the risks of severe sedation and potentially fatal respiratory depression when combined with opiates, (2) with prolonged use, the risks of abuse, misuse, and addiction which can lead to overdose and death, and (3) with continued use, the risks of physical and psychological dependence and severe potentially life-threatening withdrawal symptoms if discontinued suddenly. Benzodiazepines are all categorized as Schedule IV controlled substances, having potential for dependence, tolerance, and abuse.</p></div><div id="Estazolam.Hepatotoxicity"><h3>Hepatotoxicity</h3><p>Estazolam, as with other benzodiazepines, is rarely associated with serum ALT elevations, and clinically apparent liver injury from estazolam is extremely rare, if it occurs at all. There have been no published case reports of symptomatic, acute liver injury from estazolam. Isolated cases of clinically apparent hepatitis have been reported with other benzodiazepines including alprazolam, chlordiazepoxide, clonazepam, diazepam, flurazepam, lorazepam, and triazolam. The clinical pattern of acute liver injury from benzodiazepines is typically cholestatic and mild-to-moderate in severity with a latency of 1 to 6 months and full recovery within 1 to 2 months. Fever and rash have not been described nor has autoantibody formation.</p><p>Likelihood score: E (Unlikely cause of clinically apparent liver injury).</p></div><div id="Estazolam.Mechanism_of_Injury"><h3>Mechanism of Injury</h3><p>Estazolam is metabolized by the liver to inactive metabolites and excreted in the urine. Liver injury from benzodiazepines is probably due to the toxic effects of a rarely produced intermediate metabolite.</p></div><div id="Estazolam.Outcome_and_Management"><h3>Outcome and Management</h3><p>The case reports of hepatic injury due to benzodiazepines were followed by prompt and complete recovery upon stopping the medication, without evidence of residual or chronic injury. No cases of acute liver failure or chronic liver injury due to estazolam have been described. There is no information about cross reactivity with other benzodiazepines, but some degree of cross sensitivity may occur.</p><p>Drug Class: <a href="/books/n/livertox/Sedatives_Hypnotics/?report=reader">Sedatives and Hypnotics</a>, <a href="/books/n/livertox/BenzodiazepineDrugs/?report=reader">Benzodiazepines</a></p></div></div><div id="Estazolam.PRODUCT_INFORMATION"><h2 id="_Estazolam_PRODUCT_INFORMATION_">PRODUCT INFORMATION</h2><p>
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<b>REPRESENTATIVE TRADE NAMES</b>
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</p><p>Estazolam – Generic, ProSom® <i>(Trade name discontinued)</i></p><p>
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<b>DRUG CLASS</b>
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</p><p>Sedatives and Hypnotics</p><p>
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<a href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=estazolam" ref="pagearea=body&targetsite=external&targetcat=link&targettype=uri">COMPLETE LABELING</a>
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</p><p>Product labeling at DailyMed, National Library of Medicine, NIH</p></div><div id="Estazolam.CHEMICAL_FORMULA_AND_STRUCTURE"><h2 id="_Estazolam_CHEMICAL_FORMULA_AND_STRUCTURE_">CHEMICAL FORMULA AND STRUCTURE</h2><div class="iconblock whole_rhythm clearfix ten_col table-wrap" id="figEstazolamTc"><a href="/books/NBK548660/table/Estazolam.Tc/?report=objectonly" target="object" title="Table" class="img_link icnblk_img figpopup" rid-figpopup="figEstazolamTc" rid-ob="figobEstazolamTc"><img class="small-thumb" src="/books/NBK548660/table/Estazolam.Tc/?report=thumb" src-large="/books/NBK548660/table/Estazolam.Tc/?report=previmg" alt="Image " /></a><div class="icnblk_cntnt"><h4 id="Estazolam.Tc"><a href="/books/NBK548660/table/Estazolam.Tc/?report=objectonly" target="object" rid-ob="figobEstazolamTc">Table</a></h4></div></div></div><div id="Estazolam.ANNOTATED_BIBLIOGRAPHY"><h2 id="_Estazolam_ANNOTATED_BIBLIOGRAPHY_">ANNOTATED BIBLIOGRAPHY</h2><p>References updated: 22 June 2023</p><ul class="first-line-outdent"><li><div class="bk_ref" id="Estazolam.REF.zimmerman.1999">Zimmerman HJ. Benzodiazepines. Psychotropic and anticonvulsant agents. In, Zimmerman HJ. Hepatotoxicity: the adverse effects of drugs and other chemicals on the liver. 2nd ed. Philadelphia: Lippincott, 1999, pp. 491-3.<div><i>(Expert review of benzodiazepines and liver injury published in 1999; mentions rare instances of cholestatic hepatitis have been reported due to alprazolam, chlordiazepoxide, diazepam, flurazepam, and triazolam, and hepatocellular injury with clorazepate and clotiazepam, but no reports of hepatic injury with lorazepam, oxazepam, or temazepam).</i></div></div></li><li><div class="bk_ref" id="Estazolam.REF.larrey.2013">Larrey D, Ripault MP. Benzodiazepines. Hepatotoxicity of psychotropic drugs and drugs of abuse. In, Kaplowitz N, DeLeve LD, eds. Drug-induced liver disease. 3rd ed. Amsterdam: Elsevier, 2013, p. 455.<div><i>(Review of drug induced liver injury due to psychotropic drugs; rare instances of acute liver injury [usually cholestatic] have been reported with alprazolam, chlordiazepoxide, diazepam, flurazepam, and triazolam; a hepatitis-like pattern has been reported with clonazepam and clorazepate; no mention of estazolam).</i></div></div></li><li><div class="bk_ref" id="Estazolam.REF.mihic.2018">Mihic SJ, Mayfield J, Harris RA. Hypnotics and sedatives. In, Brunton LL, Hilal-Dandan R, Knollman BC, eds. Goodman & Gilman’s the pharmacological basis of therapeutics. 13th ed. New York: McGraw-Hill, 2018, pp. 339-53.<div><i>(Textbook of pharmacology and therapeutics).</i></div></div></li><li><div class="bk_ref" id="Estazolam.REF.davion.1985.117">Davion T, Capron-Chivrac D, Andrejak M, Capron JP. <span><span class="ref-journal">Gastroenterol Clin Biol. </span>1985;<span class="ref-vol">9</span>:117–26.</span> [Hepatitis due to antiepileptic agents] [<a href="https://pubmed.ncbi.nlm.nih.gov/3920108" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 3920108</span></a>]<div>
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<i>(Review of hepatotoxicity of anticonvulsants; among benzodiazepines, cases of cholestatic hepatitis have been linked to chlordiazepoxide and diazepam, but liver injury from this class of drugs is exceptionally rare).</i>
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</div></div></li><li><div class="bk_ref" id="Estazolam.REF.lewis.1999.433">Lewis JH, Zimmerman HJ. Drug- and chemical-induced cholestasis. <span><span class="ref-journal">Clin Liver Dis. </span>1999;<span class="ref-vol">3</span>:433–64.</span> vii. Erratum in: Clin Liver Dis 1999; 3: 917. [<a href="https://pubmed.ncbi.nlm.nih.gov/11291233" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 11291233</span></a>]<div>
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<i>(Review of drug induced cholestatic syndromes, listing many causes including chlordiazepoxide and flurazepam; “Benzodiazepines may cause cholestatic injury, although this is rare”).</i>
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</div></div></li><li><div class="bk_ref" id="Estazolam.REF.sabat_.2007.1401">Sabaté M, Ibáñez L, Pérez E, Vidal X, Buti M, Xiol X, Mas A, et al. Risk of acute liver injury associated with the use of drugs: a multicentre population survey. <span><span class="ref-journal">Aliment Pharmacol Ther. </span>2007;<span class="ref-vol">25</span>:1401–9.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/17539979" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 17539979</span></a>]<div>
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<i>(Among 126 cases of drug induced liver injury seen in Spain between 1993-2000, 20 were attributed to benzodiazepines including 5 for clorazepate, 5 alprazolam, 6 lorazepam and 4 diazepam, but compared to controls, relative risk of injury was increased only for clorazepate [8.3: estimated frequency 3.4 per 100,000 person-year exposures]).</i>
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</div></div></li><li><div class="bk_ref" id="Estazolam.REF.chalasani.2008.1924">Chalasani N, Fontana RJ, Bonkovsky HL, Watkins PB, Davern T, Serrano J, Yang H, Rochon J., Drug Induced Liver Injury Network (DILIN). Causes, clinical features, and outcomes from a prospective study of drug-induced liver injury in the United States. <span><span class="ref-journal">Gastroenterology. </span>2008;<span class="ref-vol">135</span>:1924–34.</span> [<a href="/pmc/articles/PMC3654244/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC3654244</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/18955056" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18955056</span></a>]<div>
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<i>(Among 300 cases of drug induced liver disease in the US collected from 2004 to 2008, none were attributed to a benzodiazepine).</i>
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</div></div></li><li><div class="bk_ref" id="Estazolam.REF.bj_rnsson.2008.281">Björnsson E. Hepatotoxicity associated with antiepileptic drugs. <span><span class="ref-journal">Acta Neurol Scand. </span>2008;<span class="ref-vol">118</span>:281–90.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/18341684" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 18341684</span></a>]<div>
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<i>(Review of hepatotoxicity of all anticonvulsants focusing upon phenytoin, valproate, carbamazepine; “Furthermore, hepatoxicity has not been convincingly shown to be associated with the use of benzodiazepines”).</i>
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</div></div></li><li><div class="bk_ref" id="Estazolam.REF.bj_rnsson.2013.1419">Björnsson ES, Bergmann OM, Björnsson HK, Kvaran RB, Olafsson S. Incidence, presentation and outcomes in patients with drug-induced liver injury in the general population of Iceland. <span><span class="ref-journal">Gastroenterology. </span>2013;<span class="ref-vol">144</span>:1419–25.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/23419359" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 23419359</span></a>]<div>
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<i>(In a population based study of drug induced liver injury from Iceland, 96 cases were identified over a 2 year period, but none were attributed to estazolam or any other benzodiazepine, despite millions of prescriptions filled yearly).</i>
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</div></div></li><li><div class="bk_ref" id="Estazolam.REF.hern_ndez.2014.231">Hernández N, Bessone F, Sánchez A, di Pace M, Brahm J, Zapata R, A, Chirino R, et al. Profile of idiosyncratic drug induced liver injury in Latin America. An analysis of published reports. <span><span class="ref-journal">Ann Hepatol. </span>2014;<span class="ref-vol">13</span>:231–9.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/24552865" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 24552865</span></a>]<div>
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<i>(Systematic review of literature on drug induced liver injury in Latin American countries published from 1996 to 2012 identified 176 cases, none of which were attributed to a benzodiazepine).</i>
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</div></div></li><li><div class="bk_ref" id="Estazolam.REF.chalasani.2015.1340">Chalasani N, Bonkovsky HL, Fontana R, Lee W, Stolz A, Talwalkar J, Reddy KR, et al. United States Drug Induced Liver Injury Network. Features and outcomes of 899 patients with drug-induced liver injury: The DILIN Prospective Study. <span><span class="ref-journal">Gastroenterology. </span>2015;<span class="ref-vol">148</span>:1340–1352.e7.</span> [<a href="/pmc/articles/PMC4446235/" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pmc">PMC free article<span class="bk_prnt">: PMC4446235</span></a>] [<a href="https://pubmed.ncbi.nlm.nih.gov/25754159" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 25754159</span></a>]<div>
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<i>(Among 899 cases of drug induced liver injury enrolled in a US prospective study between 2004 and 2013, no cases were attributed to estazolam or any other benzodiazepine).</i>
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</div></div></li><li><div class="bk_ref" id="Estazolam.REF12">Drugs for chronic insomnia. <span><span class="ref-journal">Med Lett Drugs Ther. </span>2023;<span class="ref-vol">65</span>:1–6.</span> [<a href="https://pubmed.ncbi.nlm.nih.gov/36630579" ref="pagearea=cite-ref&targetsite=entrez&targetcat=link&targettype=pubmed">PubMed<span class="bk_prnt">: 36630579</span></a>]<div>
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<i>(Concise review of drugs for chronic insomnia mentions that tolerance and dependence can occur with use of benzodiazepines and their use should be discouraged, and that benzodiazepines are CNS suppressants and can impair next day performance including driving and can cause complex behavior disorders, anterograde amnesia, dependence, tolerance, abuse and rebound insomnia; no mention of ALT elevations or hepatotoxicity).</i>
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</div></div></li></ul></div><div id="bk_toc_contnr"></div></div></div><div class="fm-sec"><h2 id="_NBK548660_pubdet_">Publication Details</h2><h3>Publication History</h3><p class="small">Last Update: <span itemprop="dateModified">June 22, 2023</span>.</p><h3>Copyright</h3><div><div class="half_rhythm"><a href="/books/about/copyright/">Copyright Notice</a></div></div><h3>Publisher</h3><p><a href="https://www.niddk.nih.gov/" ref="pagearea=page-banner&targetsite=external&targetcat=link&targettype=publisher">National Institute of Diabetes and Digestive and Kidney Diseases</a>, Bethesda (MD)</p><h3>NLM Citation</h3><p>LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Estazolam. [Updated 2023 Jun 22].<span class="bk_cite_avail"></span></p></div><div class="small-screen-prev"><a href="/books/n/livertox/Esmolol/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M75,30 c-80,60 -80,0 0,60 c-30,-60 -30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Prev</text></svg></a></div><div class="small-screen-next"><a href="/books/n/livertox/Estrogens/?report=reader"><svg xmlns="http://www.w3.org/2000/svg" viewBox="0 0 100 100" preserveAspectRatio="none"><path d="M25,30c80,60 80,0 0,60 c30,-60 30,0 0,-60"></path><text x="20" y="28" textLength="60" style="font-size:25px">Next</text></svg></a></div></article><article data-type="table-wrap" id="figobEstazolamTc"><div id="Estazolam.Tc" class="table"><p class="large-table-link" style="display:none"><span class="right"><a href="/books/NBK548660/table/Estazolam.Tc/?report=objectonly" target="object">View in own window</a></span></p><div class="large_tbl" id="__Estazolam.Tc_lrgtbl__"><table><thead><tr><th id="hd_h_Estazolam.Tc_1_1_1_1" scope="col" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">DRUG</th><th id="hd_h_Estazolam.Tc_1_1_1_2" scope="col" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">CAS REGISTRY NUMBER</th><th id="hd_h_Estazolam.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_Estazolam.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_Estazolam.Tc_1_1_1_1" scope="row" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">Estazolam</td><td headers="hd_h_Estazolam.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/134997768" ref="pagearea=body&targetsite=entrez&targetcat=link&targettype=pubchem">29975-16-4</a>
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</td><td headers="hd_h_Estazolam.Tc_1_1_1_3" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">C16-H11-Cl-N4</td><td headers="hd_h_Estazolam.Tc_1_1_1_4" rowspan="1" colspan="1" style="text-align:left;vertical-align:top;">
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<a href="https://pubchem.ncbi.nlm.nih.gov/substance/134997768" 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=134997768" alt="image 134997768 in the ncbi pubchem database" /></a>
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