<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3048</id>
  <title>T3D3006</title>
  <common-name>Phenobarbital</common-name>
  <description>Phenobarbital is only found in individuals that have used or taken this drug. It is a barbituric acid derivative that acts as a nonselective central nervous system depressant. It promotes binding to inhibitory gamma-aminobutyric acid subtype receptors, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations. [PubChem] Phenobarbital acts on GABAA receptors, increasing synaptic inhibition. This has the effect of elevating seizure threshold and reducing the spread of seizure activity from a seizure focus. Phenobarbital may also inhibit calcium channels, resulting in a decrease in excitatory transmitter release. The sedative-hypnotic effects of phenobarbital are likely the result of its effect on the polysynaptic midbrain reticular formation, which controls CNS arousal.</description>
  <cas>50-06-6</cas>
  <pubchem-id>4763</pubchem-id>
  <chemical-formula>C12H12N2O3</chemical-formula>
  <weight>232.084790</weight>
  <appearance>White powder.</appearance>
  <melting-point>174°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>1110 mg/L (at 25°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Absorbed in varying degrees following oral, rectal or parenteral administration. The salts are more rapidly absorbed than are the acids. The rate of absorption is increased if the sodium salt is ingested as a dilute solution or taken on an empty stomach.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Phenobarbital acts on GABAA receptors, increasing synaptic inhibition. This has the effect of elevating seizure threshold and reducing the spread of seizure activity from a seizure focus. Phenobarbital may also inhibit calcium channels, resulting in a decrease in excitatory transmitter release. The sedative-hypnotic effects of phenobarbital are likely the result of its effect on the polysynaptic midbrain reticular formation, which controls CNS arousal.</mechanism-of-toxicity>
  <metabolism>Hepatic (mostly via CYP2C19).Half Life: 53 to 118 hours (mean 79 hours)</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>2B, possibly carcinogenic to humans. (L135)</carcinogenicity>
  <use-source>For the treatment of all types of seizures except absence seizures.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive. May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease.</health-effects>
  <symptoms>CNS and respiratory depression which may progress to Cheyne-Stokes respiration, areflexia, constriction of the pupils to a slight degree (though in severe poisoning they may wshow paralytic dilation), oliguria, tachycardia, hypotension, lowered body temperature, and coma. Typical shock syndrome (apnea, circulatory collapse, respiratory arrest, and death) may occur.</symptoms>
  <treatment>Treatment of overdosage is mainly supportive and consists of maintaining an adequate airway with assisted respiration and oxygen administration as necessary, as well as monitoring of vital signs and fluid balance. If the patient is conscious and has not lost the gag reflex, emesis may be induced with ipecac. Care should be taken to prevent pulmonary aspiration of vomitus. After completion of vomiting, 30 grams activated charcoal in a glass of water may be administered. If emesis is contraindicated, gastric lavage may be performed with a cuffed endotracheal tube in place with the patient in the face down position. Activated charcoal may be left in the emptied stomach and a saline cathartic administered. Fluid therapy and other standard treatment for shock should be performed if needed. If renal function is normal, forced diuresis may aid in the elimination of the barbiturate. Alkalinization of the urine increases renal excretion of some barbiturates, especially phenobarbital, also aprobarbital, and mephobarbital (which is metabolized to phenobarbital). Although not recommended as a routine procedure, hemodialysis may be used in severe barbiturate intoxications or if the patient is anuric or in shock. Patient should be rolled from side to side every 30 minutes, and antibiotics should be given if pneumonia is suspected. Appropriate nursing care to prevent hypostatic pneumonia, decubiti, aspiration and other complications of patients with altered states of consciousness should also be performed. (L1712) </treatment>
  <created-at type="dateTime">2009-07-21T20:28:32Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:55Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Phenobarbital</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C07434</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>8069</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Phenobarbital</stitch-id>
  <drugbank-id>DB01174</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>CCC1(C(O)=NC(=O)N=C1O)C1=CC=CC=C1</moldb-smiles>
  <moldb-formula>C12H12N2O3</moldb-formula>
  <moldb-inchi>InChI=1S/C12H12N2O3/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16/h3-7H,2H2,1H3,(H2,13,14,15,16,17)</moldb-inchi>
  <moldb-inchikey>InChIKey=DDBREPKUVSBGFI-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">232.2353</moldb-average-mass>
  <moldb-mono-mass type="decimal">232.08479226</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>1.47</logp>
  <hmdb-id>HMDB15305</hmdb-id>
  <chembl-id>CHEMBL40</chembl-id>
  <chemspider-id>4599</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;Tong Sun, Shawn Watson, Rajesh Manchanda, &amp;#8220;&lt;span class="caps"&gt;PHENOBARBITAL&lt;/span&gt; &lt;span class="caps"&gt;SALTS&lt;/span&gt;; &lt;span class="caps"&gt;METHODS&lt;/span&gt; OF &lt;span class="caps"&gt;MAKING&lt;/span&gt;; &lt;span class="caps"&gt;AND&lt;/span&gt; &lt;span class="caps"&gt;METHODS&lt;/span&gt; OF &lt;span class="caps"&gt;USE&lt;/span&gt; &lt;span class="caps"&gt;THEREOF&lt;/span&gt;.&amp;#8221; U.S. Patent US20100035904, issued February 11, 2010.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
