<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3798</id>
  <title>T3D3744</title>
  <common-name>Fumitremorgin C</common-name>
  <description>Fumitremorgin C is produced by Aspergillus fumigatus and Neosartorya fischeri.</description>
  <cas>118974-02-0</cas>
  <pubchem-id>403923</pubchem-id>
  <chemical-formula>C22H25N3O3</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>259.5 - 260.5°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility nil="true"/>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Fumitremorgin C inhibits ATP-binding cassette transporter (ACBG2), also known as breast cancer resistance protein. ACBG2 is known to confer multidrug resistance and also affects the bioavailability of different drugs. Thus fumitremorgin C is often used to sensitize cancer patients to chemotherapeutic drugs. Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. They are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. This would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, then lead to decreased levels of neurotransmitter in the synapse. (A2974, A2975, A2976, A3027)</mechanism-of-toxicity>
  <metabolism></metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Fumitremorgin C is a mycotoxin that has been found in the fungus Aspergillus fumigatus. (A3024)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Tremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as 'staggers syndrome'. (A2976)
</health-effects>
  <symptoms>Tremorgenic mycotoxins affect central nervous system activity, inducing neurologic symptoms including mental confusion, paralysis, tremors, seizures, and death. They cause a neurological disease of cattle known as "staggers syndrome", which is characterized by muscle tremors and hyperexcitability. (A2976) 
</symptoms>
  <treatment>To control severe tremors caused by tremorgenic mycotoxins, methocarbamol should be administered. Generalized seizures may be treated with diazepam followed by methocarbamol or a barbiturate such as pentobarbital sodium. Gastric lavage should be performed and activated charcoal administered to limit further absorption of toxins. (A744)</treatment>
  <created-at type="dateTime">2010-05-10T15:03:52Z</created-at>
  <updated-at type="dateTime">2026-03-31T20:50:41Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <uniprot-id nil="true"/>
  <kegg-compound-id nil="true"/>
  <omim-id nil="true"/>
  <chebi-id nil="true"/>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id nil="true"/>
  <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>COC1=CC2=C(C=C1)C1=C(N2)C(C=C(C)C)N2C(C1)C(=O)N1CCCC1C2=O</moldb-smiles>
  <moldb-formula>C22H25N3O3</moldb-formula>
  <moldb-inchi>InChI=1S/C22H25N3O3/c1-12(2)9-18-20-15(14-7-6-13(28-3)10-16(14)23-20)11-19-21(26)24-8-4-5-17(24)22(27)25(18)19/h6-7,9-10,17-19,23H,4-5,8,11H2,1-3H3</moldb-inchi>
  <moldb-inchikey>DBEYVIGIPJSTOR-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">379.4522</moldb-average-mass>
  <moldb-mono-mass type="decimal">379.189591681</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB38642</hmdb-id>
  <chembl-id nil="true"/>
  <chemspider-id>357779</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 nil="true"/>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002712</chemdb-id>
  <dsstox-id>DTXSID10328045</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00011723</susdat-id>
  <iupac>7-methoxy-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁵,¹⁹]icosa-3(11),4(9),5,7-tetraene-14,20-dione</iupac>
</compound>
