Methysergide

<p><b>Methysergide</b> (<b>1-<a href="http://en.wikipedia.org/wiki/Methyl" title="Methyl" class="mw-redirect">methyl</a>-<i>D</i>-<a href="http://en.wikipedia.org/wiki/Lysergic_acid" title="Lysergic acid">lysergic acid</a> <a href="http://en.wikipedia.org/wiki/Butanol" title="Butanol">butanol</a><a href="http://en.wikipedia.org/wiki/Amide" title="Amide">amide</a></b> or <b>UML-491</b>) is a prescription drug formerly used for prophylaxis of <a href="http://en.wikipedia.org/wiki/Cluster_headaches" title="Cluster headaches" class="mw-redirect">cluster headaches</a>/<a href="http://en.wikipedia.org/wiki/Migraine_headaches" title="Migraine headaches" class="mw-redirect">migraine headaches</a>, but is no longer recommended due to <a href="http://en.wikipedia.org/wiki/Retroperitoneal_fibrosis" title="Retroperitoneal fibrosis">retroperitoneal</a>/retropulmonary fibrosis.

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<h2>Contents</h2>

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<ul>

<li class="toclevel-1 tocsection-1"><a href="http://en.wikipedia.org/wiki/Methysergide#Medical_uses">1 Medical uses</a></li>

<li class="toclevel-1 tocsection-2"><a href="http://en.wikipedia.org/wiki/Methysergide#Side_effects">2 Side effects</a></li>

<li class="toclevel-1 tocsection-3"><a href="http://en.wikipedia.org/wiki/Methysergide#Pharmacology">3 Pharmacology</a></li>

<li class="toclevel-1 tocsection-4"><a href="http://en.wikipedia.org/wiki/Methysergide#History">4 History</a></li>

<li class="toclevel-1 tocsection-5"><a href="http://en.wikipedia.org/wiki/Methysergide#Synthesis">5 Synthesis</a></li>

<li class="toclevel-1 tocsection-7"><a href="http://en.wikipedia.org/wiki/Methysergide#References">7 References</a></li>

<li class="toclevel-1 tocsection-8"><a href="http://en.wikipedia.org/wiki/Methysergide#External_links">8 External links</a></li>

</ul>

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<h2>Medical uses</h2>

<p>Methysergide is used to treat headaches such as migraine and other recurrent throbbing headaches.<sup id="cite_ref-tranquilene.com_1-0" class="reference"><a href="http://en.wikipedia.org/wiki/Methysergide#cite_note-tranquilene.com-1">[1]</a></sup> Methysergide is one of the most effective<sup id="cite_ref-Tam_2-0" class="reference"><a href="http://en.wikipedia.org/wiki/Methysergide#cite_note-Tam-2">[2]</a></sup> medications for the prevention of migraine, but not for the treatment of an acute attack.

It is also used in <a href="http://en.wikipedia.org/wiki/Carcinoid_syndrome" title="Carcinoid syndrome">carcinoid syndrome</a> to treat severe <a href="http://en.wikipedia.org/wiki/Diarrhea" title="Diarrhea">diarrhea</a>.<sup id="cite_ref-tranquilene.com_1-1" class="reference"><a href="http://en.wikipedia.org/wiki/Methysergide#cite_note-tranquilene.com-1">[1]</a></sup> It may also be used in the treatment of serotonin syndrome.<sup id="cite_ref-3" class="reference"><a href="http://en.wikipedia.org/wiki/Methysergide#cite_note-3">[3]</a></sup></p>

<h2>Side effects</h2>

<p>It has a known <a href="http://en.wikipedia.org/wiki/Adverse_drug_reaction" title="Adverse drug reaction">side effect</a>, <a href="http://en.wikipedia.org/wiki/Retroperitoneal_fibrosis" title="Retroperitoneal fibrosis">retroperitoneal fibrosis</a>,<sup id="cite_ref-4" class="reference"><a href="http://en.wikipedia.org/wiki/Methysergide#cite_note-4">[4]</a></sup> which is severe, although uncommon. Other severe but uncommon side effects include pleural fibrosis, and subendocardial fibrosis.

In addition, there is an increased risk of left-sided <a href="http://en.wikipedia.org/wiki/Cardiac_valve_dysfunction" title="Cardiac valve dysfunction" class="mw-redirect">cardiac valve dysfunction</a>.<sup id="cite_ref-Tam_2-1" class="reference"><a href="http://en.wikipedia.org/wiki/Methysergide#cite_note-Tam-2">[2]</a></sup><sup id="cite_ref-mayo_5-0" class="reference"><a href="http://en.wikipedia.org/wiki/Methysergide#cite_note-mayo-5">[5]</a></sup><sup class="noprint Inline-Template">[<i><a href="http://en.wikipedia.org/wiki/Wikipedia:Link_rot" title="Wikipedia:Link rot">dead link</a></i>]</sup></p>

<h2>Pharmacology</h2>

<p>Methysergide interacts with <a href="http://en.wikipedia.org/wiki/5-HT_receptor" title="5-HT receptor">serotonin (5-HT) receptors</a>. Its <a href="http://en.wikipedia.org/wiki/Therapeutic_effect" title="Therapeutic effect">therapeutic effect</a> in migraine <a href="http://en.wikipedia.org/wiki/Prophylaxis" title="Prophylaxis" class="mw-redirect">prophylaxis</a> has been associated with its antagonism at the <a href="http://en.wikipedia.org/wiki/5-HT2B" title="5-HT2B" class="mw-redirect">5-HT<sub>2B</sub> receptor</a>.<sup id="cite_ref-pmid8743744_6-0" class="reference"><a href="http://en.wikipedia.org/wiki/Methysergide#cite_note-pmid8743744-6">[6]</a></sup> Furthermore, it is an <a href="http://en.wikipedia.org/wiki/Receptor_antagonist" title="Receptor antagonist">antagonist</a> at the <a href="http://en.wikipedia.org/wiki/5-HT2C" title="5-HT2C" class="mw-redirect">5-HT<sub>2C</sub> receptor</a>, while at the <a href="http://en.wikipedia.org/wiki/5-HT1A" title="5-HT1A" class="mw-redirect">5-HT<sub>1A</sub> receptor</a> it serves as a partial agonist.<sup id="cite_ref-Rang187_7-0" class="reference"><a href="http://en.wikipedia.org/wiki/Methysergide#cite_note-Rang187-7">[7]</a></sup><sup id="cite_ref-pmid2933009_8-0" class="reference"><a href="http://en.wikipedia.org/wiki/Methysergide#cite_note-pmid2933009-8">[8]</a></sup><sup id="cite_ref-9" class="reference"><a href="http://en.wikipedia.org/wiki/Methysergide#cite_note-9">[9]</a></sup> It is known to have <a href="http://en.wikipedia.org/wiki/Partial_agonist" title="Partial agonist">partial agonist</a> effects on some of the other 5-HT receptors as well.<sup id="cite_ref-pmid510385_10-0" class="reference"><a href="http://en.wikipedia.org/wiki/Methysergide#cite_note-pmid510385-10">[10]</a></sup> Methysergide is metabolised into <a href="http://en.wikipedia.org/wiki/Methylergometrine" title="Methylergometrine">methylergometrine</a> in humans, which is responsible for its psychedelic effects.<sup id="cite_ref-11" class="reference"><a href="http://en.wikipedia.org/wiki/Methysergide#cite_note-11">[11]</a></sup></p>

<h2>History</h2>

<p>Methysergide was approved by the <a href="http://en.wikipedia.org/wiki/Food_and_Drug_Administration_%28United_States%29" title="Food and Drug Administration (United States)" class="mw-redirect">U.S. Food and Drug Administration</a> (FDA) in 1962.

<a href="http://en.wikipedia.org/wiki/Novartis" title="Novartis">Novartis</a> withdrew it from the U.S. market after taking over <a href="http://en.wikipedia.org/wiki/Sandoz" title="Sandoz" class="mw-redirect">Sandoz</a>, but currently lists it as a product.<sup class="noprint Inline-Template Template-Fact" >[<i><a href="http://en.wikipedia.org/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a></i>]</sup></p>

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<ul>

<li><a href="https://en.wikipedia.org/wiki/Methysergide" title="Methysergide">Methysergide</a> (UML-491)

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<li>INN: methysergide</li>

<li>IUPAC name: (8<i>beta</i>)−9,10-didehydro-<i>N</i>-(1-(hydroxymethyl)propyl)−1,6-dimethyl-ergoline-8-carboxamide</li>

<li>CAS number: <a class="external text" href="https://tools.wmflabs.org/magnustools/cas.php?language=en&cas=361-37-5&title=">361-37-5</a></li>

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Methysergide

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