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CHEBI:72564 - temozolomide

Default Structure
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:
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.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
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
temozolomidaWHO MedNet
temozolomideChemIDplus
témozolomideWHO MedNet
temozolomidumWHO MedNet
Synonyms  Source
3,4-dihydro-3-methyl-4-oxoimidazo(5,1-d)-1,2,3,5-tetrazine-8-carboxamideChemIDplus
3,4-dihydro-3-methyl-4-oxoimidazo(5,1-d)-as-tetrazine-8-carboxamideChemIDplus
3-methyl-4-oxo-3,4-dihydroimidazo(5,1-d)(1,2,3,5)tetrazine-8-carboxamideChemIDplus
8-carbamoyl-3-methylimidazo(5,1-d)-1,2,3,5-tetrazin-4(3H)-oneChemIDplus
BRN 5547136ChemIDplus
CCRG 81045ChemIDplus
Brand Names  Source
TemodalKEGG DRUG
TemodarChEBI
Manual XrefsDatabases
2589DrugCentral
D06067KEGG DRUG
DB00853DrugBank
DE3231255Patent
HMDB0014991HMDB
LSM-4590LINCS
TemozolomideWikipedia
Registry NumbersSources
Reaxys:5547136Reaxys
CAS:85622-93-1ChemIDplus
Citations