EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:72564 - temozolomide

ChEBI IDCHEBI:72564
ChEBI Nametemozolomide
Stars
DefinitionAn imidazotetrazine that is 3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine which is substituted at positions 3, 4, and 8 by methyl, oxo, and carboxamide groups, respectively. A prodrug for MTIC (5-(3-methyltriaz-1-en-1-yl)-1H-imidazole-4-carboxamide, formed by spontaneous hydrolysis of temozolomide in the body), it is used as an oral alkylating agent for the treatment of newly diagnosed malignant glioblastoma multiforme (concomitantly with radiotherapy) and malignant melanoma.
Last Modified22 February 2017
SubmitterGareth Owen
DownloadsMolfile
FormulaC6H6N6O2
Net Charge0
Average Mass194.154
Monoisotopic Mass194.05522
SMILESCn1nnc2c(C(N)=O)ncn2c1=O
InChIInChI=1S/C6H6N6O2/c1-11-6(14)12-2-8-3(4(7)13)5(12)9-10-11/h2H,1H3,(H2,7,13)
InChIKeyBPEGJWRSRHCHSN-UHFFFAOYSA-N
Wikipedia
Roles Classification
Biological Role:
alkylating agent  Highly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
ChEBI Ontology
Outgoing Relation(s)
temozolomide (CHEBI:72564) has role alkylating agent (CHEBI:22333)
temozolomide (CHEBI:72564) has role antineoplastic agent (CHEBI:35610)
temozolomide (CHEBI:72564) has role prodrug (CHEBI:50266)
temozolomide (CHEBI:72564) is a imidazotetrazine (CHEBI:72565)
temozolomide (CHEBI:72564) is a monocarboxylic acid amide (CHEBI:29347)
temozolomide (CHEBI:72564) is a triazene derivative (CHEBI:72573)
IUPAC Name 
3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide
INNs  Source
temozolomideChemIDplus
temozolomidumWHO MedNet
témozolomideWHO MedNet
temozolomidaWHO MedNet
Synonyms  Source
3,4-dihydro-3-methyl-4-oxoimidazo(5,1-d)-1,2,3,5-tetrazine-8-carboxamideChemIDplus
3-methyl-4-oxo-3,4-dihydroimidazo(5,1-d)(1,2,3,5)tetrazine-8-carboxamideChemIDplus
3,4-dihydro-3-methyl-4-oxoimidazo(5,1-d)-as-tetrazine-8-carboxamideChemIDplus
8-carbamoyl-3-methylimidazo(5,1-d)-1,2,3,5-tetrazin-4(3H)-oneChemIDplus
MB 39831ChemIDplus
methazolastoneChemIDplus
Brand Names  Source
TemodarChEBI
TemodalKEGG DRUG
Manual XrefsDatabases
TemozolomideWikipedia
D06067KEGG DRUG
HMDB0014991HMDB
DB00853DrugBank
DE3231255Patent
LSM-4590LINCS
2589DrugCentral
Registry NumbersSources
Reaxys:5547136Reaxys
CAS:85622-93-1ChemIDplus
Citations