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CHEBI:231678 - evofosfamide

ChEBI IDCHEBI:231678
ChEBI Nameevofosfamide
Stars
DefinitionA member of the class of imidazoles that is 1H-imidazole substituted by methyl, nitro, and ({bis[(2-bromoethyl)amino]phosphoryl}oxy)methyl groups at positions 1, 2 and 5, respectively. It is a hypoxia-activated prodrug that targets hypoxic regions of tumors. The drug was being evaluated for first-line treatment of advanced pancreatic adenocarcinoma and advanced soft tissue sarcoma, in combination with chemotherapy (phase 3 trial now discontinued since the drug did not meet primary endpoints).
Last Modified14 August 2024
Submitteramillett1
DownloadsMolfile
FormulaC9H16Br2N5O4P
Net Charge0
Average Mass449.040
Monoisotopic Mass446.93066
SMILESCn1c(COP(=O)(NCCBr)NCCBr)cnc1[N+](=O)[O-]
InChIInChI=1S/C9H16Br2N5O4P/c1-15-8(6-12-9(15)16(17)18)7-20-21(19,13-4-2-10)14-5-3-11/h6H,2-5,7H2,1H3,(H2,13,14,19)
InChIKeyUGJWRPJDTDGERK-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
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)
evofosfamide (CHEBI:231678) has role alkylating agent (CHEBI:22333)
evofosfamide (CHEBI:231678) has role antineoplastic agent (CHEBI:35610)
evofosfamide (CHEBI:231678) has role prodrug (CHEBI:50266)
evofosfamide (CHEBI:231678) is a C-nitro compound (CHEBI:35716)
evofosfamide (CHEBI:231678) is a imidazoles (CHEBI:24780)
evofosfamide (CHEBI:231678) is a organobromine compound (CHEBI:37141)
evofosfamide (CHEBI:231678) is a phosphorodiamidate ester (CHEBI:60284)
evofosfamide (CHEBI:231678) is a tertiary amino compound (CHEBI:50996)
IUPAC Name 
(1-methyl-2-nitro-1H-imidazol-5-yl)methyl N,N'-bis(2-bromoethyl)phosphorodiamidate
INNs  Source
évofosfamideWHO MedNet
evofosfamidumWHO MedNet
evofosfamidaWHO MedNet
evofosfamideWHO MedNet
Synonyms  Source
TH-302SUBMITTER
TH302SUBMITTER
TH 302ChEBI
2-bromo-N-[(2-bromoethylamino)-[(3-methyl-2-nitroimidazol-4-yl)methoxy]phosphoryl]ethanamineChEBI
HAP-302DrugBank
Manual XrefsDatabases
DB06091DrugBank
D10704KEGG DRUG
EvofosfamideWikipedia
Registry NumbersSources
CAS:918633-87-1SUBMITTER
Citations