CHEBI:72564 - temozolomide

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ChEBI Name temozolomide
ChEBI ID CHEBI:72564
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C6H6N6O2
Net Charge 0
Average Mass 194.15080
Monoisotopic Mass 194.055
InChI InChI=1S/C6H6N6O2/c1-11-6(14)12-2-8-3(4(7)13)5(12)9-10-11/h2H,1H3,(H2,7,13)
InChIKey BPEGJWRSRHCHSN-UHFFFAOYSA-N
SMILES Cn1nnc2c(ncn2c1=O)C(N)=O
Roles Classification
Biological Role(s): 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.
Application(s): 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.
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ChEBI Ontology
Outgoing 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 Sources
temozolomida WHO MedNet
témozolomide WHO MedNet
temozolomide ChemIDplus
temozolomidum WHO MedNet
Synonyms Sources
3,4-dihydro-3-methyl-4-oxoimidazo(5,1-d)-1,2,3,5-tetrazine-8-carboxamide ChemIDplus
3,4-dihydro-3-methyl-4-oxoimidazo(5,1-d)-as-tetrazine-8-carboxamide ChemIDplus
3-methyl-4-oxo-3,4-dihydroimidazo(5,1-d)(1,2,3,5)tetrazine-8-carboxamide ChemIDplus
8-carbamoyl-3-methylimidazo(5,1-d)-1,2,3,5-tetrazin-4(3H)-one ChemIDplus
BRN 5547136 ChemIDplus
CCRG 81045 ChemIDplus
CCRG-81045 ChemIDplus
CCRIS 8996 ChemIDplus
M & B 39831 ChemIDplus
MB 39831 ChemIDplus
M&B 39831 ChemIDplus
methazolastone ChemIDplus
NSC 362856 ChemIDplus
Sch 52365 ChemIDplus
TMZ ChEBI
Brand Names Sources
Temodal KEGG DRUG
Temodar ChEBI
Manual Xrefs Databases
2589 DrugCentral
D06067 KEGG DRUG
DB00853 DrugBank
DE3231255 Patent
HMDB0014991 HMDB
LSM-4590 LINCS
Temozolomide Wikipedia
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Registry Numbers Types Sources
5547136 Reaxys Registry Number Reaxys
85622-93-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
22680781 PubMed citation Europe PMC
22818211 PubMed citation Europe PMC
23246370 PubMed citation Europe PMC
23254891 PubMed citation Europe PMC
23293540 PubMed citation Europe PMC
23335050 PubMed citation Europe PMC
23362460 PubMed citation Europe PMC
23377829 PubMed citation Europe PMC
23385995 PubMed citation Europe PMC
23389760 PubMed citation Europe PMC
Last Modified
22 February 2017