<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4751</id>
  <title>T3D4696</title>
  <common-name>Griseofulvin</common-name>
  <description>Griseofulvin is only found in individuals that have used or taken this drug. It is an antifungal antibiotic. Griseofulvin may be given by mouth in the treatment of tinea infections. Griseofulvin is fungistatic, however the exact mechanism by which it inhibits the growth of dermatophytes is not clear. It is thought to inhibit fungal cell mitosis and nuclear acid synthesis. It also binds to and interferes with the function of spindle and cytoplasmic microtubules by binding to alpha and beta tubulin. It binds to keratin in human cells, then once it reaches the fungal site of action, it binds to fungal microtubes thus altering the fungal process of mitosis.</description>
  <cas>126-07-8</cas>
  <pubchem-id>441140</pubchem-id>
  <chemical-formula>C17H17ClO6</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>220°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>8.64 mg/L (at 25°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Poorly absorbed from GI ranging from 25 to 70% of an oral dose. Absorption is significantly enhanced by administration with or after a fatty meal.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Griseofulvin is fungistatic, however the exact mechanism by which it inhibits the growth of dermatophytes is not clear. It is thought to inhibit fungal cell mitosis and nuclear acid synthesis. It also binds to and interferes with the function of spindle and cytoplasmic microtubules by binding to alpha and beta tubulin. It binds to keratin in human cells, then once it reaches the fungal site of action, it binds to fungal microtubes thus altering the fungal process of mitosis.</mechanism-of-toxicity>
  <metabolism>Primarily hepatic with major metabolites being 6-methyl-griseofulvin and its glucuronide conjugate.Half Life: 9-21 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>2B, possibly carcinogenic to humans. (L135)</carcinogenicity>
  <use-source>Griseofulvin is used both in animals and in humans, to treat fungal infections of the skin (commonly known as ringworm) and nails. Griseofulvin is used orally only for dermatophytosis. It is ineffective topically. Griseofulvin is reserved for cases with nail, hair or large body surface involvement. (Wikipedia)</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Side effects are minor: headaches, gastrointestinal reactions and cutaneous eruptions</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-09-11T02:05:24Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:26:55Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/Griseofulvin</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C06686</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>27779</chebi-id>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB00400</drugbank-id>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>[H][C@@]1(C)CC(=O)C=C(OC)[C@@]11OC2=C(C1=O)C(OC)=CC(OC)=C2Cl</moldb-smiles>
  <moldb-formula>C17H17ClO6</moldb-formula>
  <moldb-inchi>InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1</moldb-inchi>
  <moldb-inchikey>InChIKey=DDUHZTYCFQRHIY-RBHXEPJQSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">352.766</moldb-average-mass>
  <moldb-mono-mass type="decimal">352.071365983</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>2.18</logp>
  <hmdb-id>HMDB14544</hmdb-id>
  <chembl-id>CHEMBL562</chembl-id>
  <chemspider-id>389934</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;Gary Liversidge, &amp;#8220;Methods of making and using novel griseofulvin compositions.&amp;#8221; U.S. Patent US20070098805, issued May 03, 2007.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
