18F-EF5

18F-EF5
Names
	IUPAC name 2-(2-Nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide
	Other names NSC-684681; EF-5
Identifiers
CAS Number	152721-37-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	344807 ;
PubChem CID	389053;
UNII	383HJ2T87O ;
CompTox Dashboard (EPA)	DTXSID10165114 ;
	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) Key: JGGDSDPOPRWSCX-UHFFFAOYSA-N ;
	SMILES O=[N+]([O-])c1nccn1CC(=O)NCC(F)(F)C(F)(F)F;
Properties
Chemical formula	C8H7F5N4O3
Molar mass	302.161 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

EF5 is a nitroimidazole derivative used in oncology research.[1] Due to its similarity in chemical structure to etanidazole, EF5 binds in cells displaying hypoxia.[2]

The ¹⁸F-radiolabeled derivative of EF5 is being studied for its possibility to be used in positron emission tomography (PET) to detect low levels of oxygen in brain tumors.[3] This can help show how a tumor will respond to treatment.

References

Evans, Sydney M.; Fraker, Douglas; Hahn, Stephen M.; Gleason, Kristen; Jenkins, W. Timothy; Jenkins, Kevin; Hwang, Wei-Ting; Zhang, Paul; Mick, Rosemarie; Koch, Cameron J (2006). "EF5 binding and clinical outcome in human soft tissue sarcomas". International Journal of Radiation Oncology, Biology, Physics. 64 (3): 922–927. doi:10.1016/j.ijrobp.2005.05.068.
Lord, Edith M.; Harwell, Lee; Koch, Cameron J. (1993). "Detection of hypoxic cells by monoclonal antibody recognizing 2-nitroimidazole adducts". Cancer Research. 53 (23): 5721–5726. PMID 8242628.
Ziemer, L. S.; Evans, S. M.; Kachur, A. V.; Shuman, A. L.; Cardi, C. A.; Jenkins, W. T.; Karp, J. S.; Alavi, A.; Dolbier, W. R.; Koch, C. J. (2003). "Noninvasive imaging of tumor hypoxia in rats using the 2-nitroimidazole 18F-EF5". European Journal of Nuclear Medicine and Molecular Imaging. 30 (2): 259–266. doi:10.1007/s00259-002-1037-5. PMID 12552344.

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[1] Evans, Sydney M.; Fraker, Douglas; Hahn, Stephen M.; Gleason, Kristen; Jenkins, W. Timothy; Jenkins, Kevin; Hwang, Wei-Ting; Zhang, Paul; Mick, Rosemarie; Koch, Cameron J (2006). "EF5 binding and clinical outcome in human soft tissue sarcomas". International Journal of Radiation Oncology, Biology, Physics. 64 (3): 922–927. doi:10.1016/j.ijrobp.2005.05.068.

[2] Lord, Edith M.; Harwell, Lee; Koch, Cameron J. (1993). "Detection of hypoxic cells by monoclonal antibody recognizing 2-nitroimidazole adducts". Cancer Research. 53 (23): 5721–5726. PMID 8242628.

[3] Ziemer, L. S.; Evans, S. M.; Kachur, A. V.; Shuman, A. L.; Cardi, C. A.; Jenkins, W. T.; Karp, J. S.; Alavi, A.; Dolbier, W. R.; Koch, C. J. (2003). "Noninvasive imaging of tumor hypoxia in rats using the 2-nitroimidazole 18F-EF5". European Journal of Nuclear Medicine and Molecular Imaging. 30 (2): 259–266. doi:10.1007/s00259-002-1037-5. PMID 12552344.