temozolomide (CHEBI:72564)

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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

Average Mass

194.15080

Monoisotopic Mass

194.05522

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.

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

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

Last Modified

22 February 2017