Evofosfamide
2-bromo-N-[(2-bromoethylamino)-[(3-methyl-2-nitroimidazol-4-yl)methoxy]phosphoryl]ethanamine
Molecular Identity
Evofosfamide
2-bromo-N-[(2-bromoethylamino)-[(3-methyl-2-nitroimidazol-4-yl)methoxy]phosphoryl]ethanamine
PubChem CID: 11984561
Evofosfamide is 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). It has a role as an alkylating agent, an antineoplastic agent and a prodrug. It is a member of imidazoles, a C-nitro compound, an organobromine compound, a tertiary amino compound and a phosphorodiamidate ester.
2D Structure
Properties
C9H16Br2N5O4P
Molecular Formula
449.04
Molecular Weight
g/mol
448.9286
Exact Mass
Da
0.6
XLogP
Drug-like (Lipinski: < 5)
114
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
7
H-Bond Acceptors
374
Complexity
SMILES
Canonical SMILES
SMILES: CN1C(=CN=C1[N+](=O)[O-])COP(=O)(NCCBr)NCCBrIsomeric SMILES
SMILES: CN1C(=CN=C1[N+](=O)[O-])COP(=O)(NCCBr)NCCBrSynonyms(20)
evofosfamide918633-87-1TH-302HAP-302TH 3022-bromo-N-[(2-bromoethylamino)-[(3-methyl-2-nitroimidazol-4-yl)methoxy]phosphoryl]ethanamineEvofosfamida8A9RZ3HN8WPhosphorodiamidic acid, N,N'-bis(2-bromoethyl)-, (1-methyl-2-nitro-1H-imidazol-5-yl)methyl esterDTXSID60238721(1-Methyl-2-nitro-1H-imidazol-5-yl)methyl N,N'-bis(2-bromoethyl)phosphorodiamidate(1-METHYL-2-NITRO-1H-IMIDAZOLE-5-YL)METHYL N,N'-BIS(2-BROMOETHYL) DIAMIDOPHOSPHATE(1-METHYL-2-NITRO-1H-IMIDAZOL-5-YL)METHYL N,N'-BIS(2-BROMOETHYL)DIAMIDOPHOSPHATE(2-bromoethyl)({[(2-bromoethyl)amino][(1-methyl-2-nitro-1H-imidazol-5-yl)methoxy]phosphoryl})amineTH302 cpd
Data from PubChem (NCBI)
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Trials and conditions connected to Evofosfamide
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