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Details

Stereochemistry ACHIRAL
Molecular Formula C8H7F5N4O3
Molecular Weight 302.1582
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EF-5

SMILES

[O-][N+](=O)C1=NC=CN1CC(=O)NCC(F)(F)C(F)(F)F

InChI

InChIKey=JGGDSDPOPRWSCX-UHFFFAOYSA-N
InChI=1S/C8H7F5N4O3/c9-7(10,8(11,12)13)4-15-5(18)3-16-2-1-14-6(16)17(19)20/h1-2H,3-4H2,(H,15,18)

HIDE SMILES / InChI

Molecular Formula C8H7F5N4O3
Molecular Weight 302.1582
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

EF5 [2-(2-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl) acetamide] is a 2-nitroimidazole-based hypoxia marker that selectively binds hypoxic cells. It is a compound developed at the University of Pennsylvania by Dr. Cameron Koch and Dr. Sydney Evans. Upon injection into animal tissues, EF5 selectively binds to hypoxic cells and forms adducts. 2-(2-Nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl) acetamide ([18F]EF5) is a specific positron emission tomography tracer approved by the US Food and Drug Administration for in vivo detection of hypoxia. EF5 has been used to detect hypoxia in rodent and human tumors, and it has shown good correlation with other hypoxia markers, such as hypoxia-inducible transcription factor. EF5 undergoes a biochemical reduction by nitroreductases in viable cells and forms covalent adducts to intracellular macromolecules in the absence of oxygen Therefore, only viable hypoxic cells are detectable with EF5. EF5 is a lipophilic compound and has better pharmacokinetic properties than other nitroimidazole compounds. [18F]EF5 positron emission tomography imaging has been introduced as a promising tool for the detection of hypoxia in tumor tissues in patients and in experimental models. Large atherosclerotic plaques in mice contained hypoxic areas and showed uptake of [18F]EF5. Despite its slow blood clearance, the high uptake of [18F]EF5 in plaques suggested that plaque hypoxia is a potential target for identifying high-risk plaques noninvasively.

Approval Year

PubMed

PubMed

TitleDatePubMed
Biodistribution and dosimetry of (18)F-EF5 in cancer patients with preliminary comparison of (18)F-EF5 uptake versus EF5 binding in human glioblastoma.
2010-11
Inhibitor of DNA binding/differentiation 2 induced by hypoxia promotes synovial fibroblast-dependent osteoclastogenesis.
2009-12
Atrasentan (ABT-627) enhances perfusion and reduces hypoxia in a human tumor xenograft model.
2009-10
Immunohistochemical detection of changes in tumor hypoxia.
2009-03-15
Imaging and analytical methods as applied to the evaluation of vasculature and hypoxia in human brain tumors.
2008-12
18F-EF5: a new PET tracer for imaging hypoxia in head and neck cancer.
2008-12
Noninvasive molecular imaging of hypoxia in human xenografts: comparing hypoxia-induced gene expression with endogenous and exogenous hypoxia markers.
2008-10-15
Changes in tumor hypoxia induced by mild temperature hyperthermia as assessed by dual-tracer immunohistochemistry.
2008-08
Importance of antibody concentration in the assessment of cellular hypoxia by flow cytometry: EF5 and pimonidazole.
2008-06
In vivo measurement of the hypoxia marker EF5 in Shionogi tumours using (19)F magnetic resonance spectroscopy.
2008-03
Hyperbaric oxygen reduces tissue hypoxia and hypoxia-inducible factor-1 alpha expression in focal cerebral ischemia.
2008-03
Imaging of tumor hypoxia to predict treatment sensitivity.
2008
Patterns and levels of hypoxia in head and neck squamous cell carcinomas and their relationship to patient outcome.
2007-11-15
In situ oxygen utilization in the rat intervertebral disc.
2007-03
Oxygen levels in normal and previously irradiated human skin as assessed by EF5 binding.
2006-12
EF5 binding and clinical outcome in human soft tissue sarcomas.
2006-03-01
Preserved placental oxygenation and development during severe systemic hypoxia.
2006-03
MCT-4, A511/Basigin and EF5 expression patterns during early chick cardiomyogenesis indicate cardiac cell differentiation occurs in a hypoxic environment.
2006-01
Measurements of hypoxia ([(18)F]-FMISO, [(18)F]-EF5) with positron emission tomography (PET) and perfusion using PET ([(15)O]-H(2)O) and power Doppler ultrasonography in feline fibrosarcomas*.
2005-12
A noninvasive approach for assessing tumor hypoxia in xenografts: developing a urinary marker for hypoxia.
2005-07-15
Significance of hypoxia in malignant glioma. Re: Evans et al. Hypoxia is important in the biology and aggression of human glial brain tumors. Clin Cancer Res 2004;10:8177-84.
2005-05-15
Stabilization of the retinal vascular network by reciprocal feedback between blood vessels and astrocytes.
2005-04
Hypoxia is important in the biology and aggression of human glial brain tumors.
2004-12-15
Utility of 19F MRS detection of the hypoxic cell marker EF5 to assess cellular hypoxia in solid tumors.
2004-12
HER-2/neu overexpression increases the viable hypoxic cell population within solid tumors without causing changes in tumor vascularization.
2004-11
Hypoxia and Photofrin uptake in the intraperitoneal carcinomatosis and sarcomatosis of photodynamic therapy patients.
2004-07-15
Hypoxia and hypoxia-inducible factor-1 target genes in central nervous system radiation injury: a role for vascular endothelial growth factor.
2004-05-15
Acute hypoxia enhances spontaneous lymph node metastasis in an orthotopic murine model of human cervical carcinoma.
2004-03-15
Role of myocardial hypoxia in the remodeling of the embryonic avian cardiac outflow tract.
2004-03-15
Comparative measurements of hypoxia in human brain tumors using needle electrodes and EF5 binding.
2004-03-01
In vivo colocalization of 2-nitroimidazole EF5 fluorescence intensity and electron paramagnetic resonance oximetry in mouse tumors.
2003-04
Noninvasive imaging of tumor hypoxia in rats using the 2-nitroimidazole 18F-EF5.
2003-02
Non-invasive PET and SPECT imaging of tissue hypoxia using isotopically labeled 2-nitroimidazoles.
2003
Activation of hypoxia-inducible factor-1 in the rat cerebral cortex after transient global ischemia: potential role of insulin-like growth factor-1.
2002-10-15
Effects of hyperglycemia on oxygenation, radiosensitivity and bioenergetic status of subcutaneous RIF-1 tumors.
2002-07
Vasa vasorum hypoperfusion is responsible for medial hypoxia and anatomic remodeling in the newborn lamb ductus arteriosus.
2002-02
Measurement of absolute oxygen levels in cells and tissues using oxygen sensors and 2-nitroimidazole EF5.
2002
Hypoxia-inducible factor-1alpha is an intrinsic marker for hypoxia in cervical cancer xenografts.
2001-10-15
Hypoxic heterogeneity in human tumors: EF5 binding, vasculature, necrosis, and proliferation.
2001-10
Characterization of the effects of antiangiogenic agents on tumor pathophysiology.
2001-10
Intravascular HBO(2) saturations, perfusion and hypoxia in spontaneous and transplanted tumor models.
2001-09-01
Pharmacokinetics of EF5 [2-(2-nitro-1-H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl) acetamide] in human patients: implications for hypoxia measurements in vivo by 2-nitroimidazoles.
2001-09
Combined prostaglandin and nitric oxide inhibition produces anatomic remodeling and closure of the ductus arteriosus in the premature newborn baboon.
2001-09
Differential effects of buthionine sulphoximine in hypoxic and non-hypoxic regions of human cervical carcinoma xenografts.
2001-07
Green fluorescent protein is a suitable reporter of tumor hypoxia despite an oxygen requirement for chromophore formation.
2001-06-14
Hypoxia in radiation-induced blood-spinal cord barrier breakdown.
2001-04-15
Hypoxia and VEGF mRNA expression in human tumors.
2001-04-06
Influence of hydralazine administration on oxygenation in spontaneous and transplanted tumor models.
2001-03-01
Hypoxia in human intraperitoneal and extremity sarcomas.
2001-02-01
[18F]-EF5, a marker for PET detection of hypoxia: synthesis of precursor and a new fluorination procedure.
2001-01
Patents

Patents

Substance Class Chemical
Created
by admin
on Mon Mar 31 18:14:55 GMT 2025
Edited
by admin
on Mon Mar 31 18:14:55 GMT 2025
Record UNII
383HJ2T87O
Record Status Validated (UNII)
Record Version
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Name Type Language
EF-5
Common Name English
NSC-684681
Preferred Name English
2-NITRO-1-H-IMIDAZOLE-1-YL)-N-(2,2,3,3,3-PENTAFLUOROPROPYL)ACETAMIDE
Common Name English
2-(2-NITRO-1H-IMIDAZOL-1-YL)-N-(2,2,3,3,3-PENTAFLUORO-PROPYL)ACETAMIDE
Systematic Name English
EF5
Common Name English
Code System Code Type Description
CAS
152721-37-4
Created by admin on Mon Mar 31 18:14:55 GMT 2025 , Edited by admin on Mon Mar 31 18:14:55 GMT 2025
PRIMARY
NCI_THESAURUS
C45873
Created by admin on Mon Mar 31 18:14:55 GMT 2025 , Edited by admin on Mon Mar 31 18:14:55 GMT 2025
PRIMARY
FDA UNII
383HJ2T87O
Created by admin on Mon Mar 31 18:14:55 GMT 2025 , Edited by admin on Mon Mar 31 18:14:55 GMT 2025
PRIMARY
WIKIPEDIA
18F-EF5
Created by admin on Mon Mar 31 18:14:55 GMT 2025 , Edited by admin on Mon Mar 31 18:14:55 GMT 2025
PRIMARY
PUBCHEM
389053
Created by admin on Mon Mar 31 18:14:55 GMT 2025 , Edited by admin on Mon Mar 31 18:14:55 GMT 2025
PRIMARY
NSC
684681
Created by admin on Mon Mar 31 18:14:55 GMT 2025 , Edited by admin on Mon Mar 31 18:14:55 GMT 2025
PRIMARY
EPA CompTox
DTXSID10165114
Created by admin on Mon Mar 31 18:14:55 GMT 2025 , Edited by admin on Mon Mar 31 18:14:55 GMT 2025
PRIMARY
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