CHEBI:4305 - dacarbazine

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ChEBI Name dacarbazine
ChEBI ID CHEBI:4305
Definition A monocarboxylic acid amide that is 1H-imidazole-4-carboxamide which is substituted at position 5 by a 3,3-dimethyltriaz-1-en-1-yl group. It is used for the treatment of metastatic malignant melanoma, and in combination with other drugs for the treatment of Hodgkin's disease and soft-tissue sarcoma.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C6H10N6O
Net Charge 0
Average Mass 182.183
Monoisotopic Mass 182.092
InChI InChI=1S/C6H10N6O/c1-12(2)11-10-6-4(5(7)13)8-3-9-6/h3H,1-2H3,(H2,7,13)(H,8,9)
InChIKey FDKXTQMXEQVLRF-UHFFFAOYSA-N
SMILES C=1NC(=C(N1)C(=O)N)N=NN(C)C
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.
carcinogenic agent
A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing dacarbazine (CHEBI:4305) has role alkylating agent (CHEBI:22333)
dacarbazine (CHEBI:4305) has role antineoplastic agent (CHEBI:35610)
dacarbazine (CHEBI:4305) has role carcinogenic agent (CHEBI:50903)
dacarbazine (CHEBI:4305) has role prodrug (CHEBI:50266)
dacarbazine (CHEBI:4305) is a imidazoles (CHEBI:24780)
dacarbazine (CHEBI:4305) is a monocarboxylic acid amide (CHEBI:29347)
dacarbazine (CHEBI:4305) is a triazene derivative (CHEBI:72573)
IUPAC Name
5-(3,3-dimethyltriaz-1-en-1-yl)-1H-imidazole-4-carboxamide
INNs Sources
dacarbazina WHO MedNet
dacarbazine WHO MedNet
dacarbazine WHO MedNet
dacarbazinum WHO MedNet
Synonyms Sources
4-(3,3-dimethyl-1-triazeno)imidazole-5-carboxamide ChemIDplus
4-(5)-(3,3-dimethyl-1-triazeno)imidazole-5(4)-carboxamide ChemIDplus
4-(dimethyltriazeno)imidazole-5-carboxamide ChemIDplus
5-(3,3-dimethyl-1-triazeno)imidazole-4-carboxamide ChemIDplus
5-(3,3-Dimethyl-1-triazeno)imidazole-4-carboxamide ChemIDplus
5-(3,3-dimethyltriazeno)imidazole-4-carboxamide ChemIDplus
5-(dimethyltriazeno)imidazole-4-carboxamide ChemIDplus
deticene DrugCentral
Di-me-triazenoimidazolecarboxamide ChemIDplus
DIC ChemIDplus
DTIC ChemIDplus
Dtic-Dome (TN) KEGG DRUG
HSDB 3219 ChemIDplus
ICDMT ChemIDplus
Imidazole-4-carboxamide, 5-(3,3-dimethyl-1-triazeno)- NIST Chemistry WebBook
NCI-C04717 ChemIDplus
NSC 45388 ChemIDplus
NSC-45388 ChemIDplus
Manual Xrefs Databases
773 DrugCentral
C06936 KEGG COMPOUND
D00288 KEGG DRUG
Dacarbazine Wikipedia
DB00851 DrugBank
View more database links
Registry Numbers Types Sources
4342-03-4 CAS Registry Number KEGG DRUG
4342-03-4 CAS Registry Number NIST Chemistry WebBook
4342-03-4 CAS Registry Number ChemIDplus
521487 Reaxys Registry Number Reaxys
521487 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
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Last Modified
19 January 2018