evofosfamide (CHEBI:231678)

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ChEBI Name	evofosfamide

ChEBI ID	CHEBI:231678

Definition	A 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).

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Alexandra Millett

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Formula

C9H16Br2N5O4P

Net Charge

Average Mass

449.040

Monoisotopic Mass

446.93067

InChI

InChI=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)

InChIKey

UGJWRPJDTDGERK-UHFFFAOYSA-N

SMILES

CN1C(COP(=O)(NCCBr)NCCBr)=CN=C1[N+]([O-])=O

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound )

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	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

Synonyms	Sources
2-bromo-N-[(2-bromoethylamino)-[(3-methyl-2-nitroimidazol-4-yl)methoxy]phosphoryl]ethanamine	ChEBI
HAP-302	DrugBank
TH 302	ChEBI
TH-302	SUBMITTER
TH302	SUBMITTER

Registry Number	Type	Source
918633-87-1	CAS Registry Number	SUBMITTER

Last Modified

14 August 2024