<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2852</id>
  <title>T3D2810</title>
  <common-name>Cimetidine</common-name>
  <description>A histamine congener, it competitively inhibits histamine binding to histamine H2 receptors. Cimetidine has a range of pharmacological actions. It inhibits gastric acid secretion, as well as pepsin and gastrins output. It also blocks the activity of cytochrome P-450 which might explain proposals for use in neoadjuvant therapy.</description>
  <cas>51481-61-9</cas>
  <pubchem-id>2756</pubchem-id>
  <chemical-formula>C10H16N6S</chemical-formula>
  <weight>252.115710</weight>
  <appearance>White powder.</appearance>
  <melting-point>142°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>9380 mg/L (at 25°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral, rapid 60-70%</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Cimetidine binds to an H&lt;sub&gt;2&lt;/sub&gt;-receptor located on the basolateral membrane of the gastric parietal cell, blocking histamine effects. This competitive inhibition results in reduced gastric acid secretion and a reduction in gastric volume and acidity.</mechanism-of-toxicity>
  <metabolism>HepaticRoute of Elimination: The principal route of excretion of cimetidine is the urine.Half Life: 2 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>3, not classifiable as to its carcinogenicity to humans. (L135)</carcinogenicity>
  <use-source>For the treatment and the management of acid-reflux disorders (GERD), peptic ulcer disease, heartburn, and acid indigestion.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Symptoms of overdose include nausea, vomiting, diarrhea, increased saliva production, difficulty breathing, and a fast heartbeat.</symptoms>
  <treatment>The usual measures to remove unabsorbed material from the gastrointestinal tract, clinical monitoring and supportive therapy should be employed. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:27:02Z</created-at>
  <updated-at type="dateTime">2026-03-31T17:03:14Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Cimetidine</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C06952</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>3699</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Cimetidine</stitch-id>
  <drugbank-id>DB00501</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>C\N=C(\NCCSCC1=C(C)NC=N1)NC#N</moldb-smiles>
  <moldb-formula>C10H16N6S</moldb-formula>
  <moldb-inchi>InChI=1S/C10H16N6S/c1-8-9(16-7-15-8)5-17-4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14)</moldb-inchi>
  <moldb-inchikey>AQIXAKUUQRKLND-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">252.339</moldb-average-mass>
  <moldb-mono-mass type="decimal">252.115715232</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>0.4</logp>
  <hmdb-id>HMDB14644</hmdb-id>
  <chembl-id>CHEMBL30</chembl-id>
  <chemspider-id>2654</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Saburo Uchikuga, Tomoyasu Tashiro, Yasuko Osawa, &amp;#8220;Process for preparing the H.sub.2 -receptor antagonist cimetidine.&amp;#8221; U.S. Patent US4413129, issued March, 1972.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002212</chemdb-id>
  <dsstox-id>DTXSID4020329</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00008665</susdat-id>
  <iupac>(Z)-N-cyano-N''-methyl-N'-(2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine</iupac>
</compound>
