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EF-5

CAT: 0804-HY-U00118-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-U00118-01Size:5 mg
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Description
EF-5 (EF5; 2-Nitroimidazole) is a hypoxia labeling agent used to identify hypoxia in cells.
CAS Number
152721-37-4
UNSPSC
12352005
Target
Biochemical Assay Reagents
Type
Reference compound
Related Pathways
Others
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/EF-5.html
Purity
98.29
Solubility
DMSO : 125 mg/mL (ultrasonic)
Smiles
O=C(NCC(F)(F)C(F)(F)F)CN1C=CN=C1[N+]([O-])=O
Molecular Formula
C8H7F5N4O3
Molecular Weight
302.16
References & Citations
[1]Wang J, et al. The 2-nitroimidazole EF5 is a biomarker for oxidoreductases that activate the bioreductive prodrug CEN-209 under hypoxia. Clin Cancer Res. 2012 Mar 15;18 (6) :1684-95.|[2]Evans SM, et al. Identification of hypoxia in cells and tissues of epigastric 9L rat glioma using EF5 [2- (2-nitro-1H-imidazol-1-yl) -N- (2,2,3,3,3-pentafluoropropyl) acetamide]. Br J Cancer. 1995 Oct;72 (4) :875-82.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Phase 2

Chemical Information

2-(2-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide

EF5 is a fluorinated derivative of the 2-nitroimidazole etanidazole. EF5 is effective in accessing oxygen levels in tumor tissue through its adduct formation to intracellular macromolecules in the absence of oxygen. Reduction of this agent is carried out by a diverse group of enzymes in the cytoplasm, microsomes and mitochondria. Tissue hypoxia detection via EF5 has been reported in several cancers, including squamous cell carcinoma of the cervix and the head and neck, and in sarcoma.

CAS Number152721-37-4
PubChem CID389053
IUPAC Name2-(2-nitroimidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
Molecular FormulaC8H7F5N4O3
Molecular Weight302.16
XLogP1.1
Topological Polar Surface Area92.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count4
Heavy Atom Count20
Formal Charge0
Complexity383
SMILES
C1=CN(C(=N1)[N+](=O)[O-])CC(=O)NCC(C(F)(F)F)(F)F
InChI
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)
InChIKey
JGGDSDPOPRWSCX-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 2-(2-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
CAS: 152721-37-4
CID: 389053
Formula: C8H7F5N4O3
MW: 302.16
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight302.16
XLogP31.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count4
Exact Mass302.04383091
Monoisotopic Mass302.04383091
Topological Polar Surface Area92.7 Ų
Heavy Atom Count20
Formal Charge0
Complexity383
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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MBS3615292-01EF-5
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sc-393731 HRPEF-1 δ (A-5) HRP
sc-393924 FITCEF-Tu (A-5) FITC
sc-393731 PEEF-1 δ (A-5) PE
sc-393924 ACEF-Tu (A-5) AC
sc-393924 PEEF-Tu (A-5) PE
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