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18F-EF5

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Targeting tumor hypoxia in cancer treatment aims to overcome radiotherapy resistance of hypoxic tumors. Thus, a major clinical implication for F-EF5-PET imaging is expected to be guiding of radiotherapy dose modulation. Clinical studies on F-EF5-PET/CT imaging have indicated clinically acceptable
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also favorable imaging characteristics, prognostic value and repeatability. A recent 18F-EF5-PET/MR study showed promising potential in detecting tumor hypoxia in cervical cancer. However, F-EF5-PET/CT is not feasible in imaging of ovarian cancer due to physiological intra-abdominal
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Komar G, Lehtiö K, Seppänen M, Eskola O, Levola H, Lindholm P, et al. (November 2014). "Prognostic value of tumour blood flow, EF5 and FDG PET/CT imaging in patients with head and neck cancer treated with radiochemotherapy".
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Lin LL, Silvoniemi A, Stubbs JB, Rengan R, Suilamo S, Solin O, et al. (September 2012). "Radiation dosimetry and biodistribution of the hypoxia tracer (18)F-EF5 in oncologic patients".
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Ziemer LS, Evans SM, Kachur AV, Shuman AL, Cardi CA, Jenkins WT, et al. (February 2003). "Noninvasive imaging of tumor hypoxia in rats using the 2-nitroimidazole 18F-EF5".
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Narva, Sara I.; Seppänen, Marko P.; Raiko, Juho R.H.; Forsback, Sarita J.; Orte, Katri J.; Virtanen, Johanna M.; Hynninen, Johanna; Hietanen, Sakari (December 2021).
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Non-labeled EF5 has been extensively used in immunohistochemical studies for several years and its hypoxia specificity has been comprehensively evaluated The
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Evans SM, Fraker D, Hahn SM, Gleason K, Jenkins WT, Jenkins K, et al. (March 2006). "EF5 binding and clinical outcome in human soft tissue sarcomas".
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Koch CJ (2002). "[1] Measurement of absolute oxygen levels in cells and tissues using oxygen sensors and 2-nitroimidazole EF5".
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Lord EM, Harwell L, Koch CJ (December 1993). "Detection of hypoxic cells by monoclonal antibody recognizing 2-nitroimidazole adducts".
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F-EF5-accumulation. Further studies evaluating the clinical use of F-EF5 PET imaging in head and neck cancer are ongoing.
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Silvoniemi A, Suilamo S, Laitinen T, Forsback S, Löyttyniemi E, Vaittinen S, et al. (February 2018).
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Measurement of absolute oxygen levels in cells and tissues using oxygen sensors and 2-nitroimidazole EF5
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Komar G, Seppänen M, Eskola O, Lindholm P, Grönroos TJ, Forsback S, et al. (December 2008).
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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)
854:"The feasibility of [F]EF5-PET/CT to image hypoxia in ovarian tumors: a clinical study" 885: 834: 826: 785: 728: 684: 643: 600: 565: 555: 524: 475: 448: 387: 756:"Repeatability of tumour hypoxia imaging using [F]EF5 PET/CT in head and neck cancer" 875: 865: 816: 775: 767: 720: 674: 635: 592: 547: 514: 506: 440: 402: 272: 131: 87: 176: 209: 880: 853: 780: 755: 519: 494: 372: 327: 852:
Laasik M, Hynninen J, Forsback S, Noponen T, Seppänen M, Hietanen S (September 2020).
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derivative used in oncology research. Due to its similarity in chemical structure to
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and several other malignant tumors. This can help show how a tumor will respond to
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Except where otherwise noted, data are given for materials in their
805:"Imaging of Tumor Hypoxia With 18F-EF5 PET/MRI in Cervical Cancer" 110: 100: 546:. Methods in Enzymology. Vol. 352. Elsevier. pp. 3–31. 433:
International Journal of Radiation Oncology, Biology, Physics
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European Journal of Nuclear Medicine and Molecular Imaging
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European Journal of Nuclear Medicine and Molecular Imaging
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European Journal of Nuclear Medicine and Molecular Imaging
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of EF5 is being studied for its possibility to be used in
495:"Optimizing hypoxia detection and treatment strategies" 344: 155: 409:biodistribution and dosimetric profile, and in 86: 8: 628:Cancer Biotherapy & Radiopharmaceuticals 208: 130: 22: 879: 869: 820: 779: 678: 518: 379:, EF5 binds in cells displaying hypoxia. 175: 397:(PET) to detect low levels of oxygen in 423: 254: 229: 204: 56:-(2,2,3,3,3-pentafluoropropyl)acetamide 236:Key: JGGDSDPOPRWSCX-UHFFFAOYSA-N 7: 146: 257:O=()c1nccn1CC(=O)NCC(F)(F)C(F)(F)F 14: 511:10.1053/j.semnuclmed.2014.10.004 493:Koch CJ, Evans SM (March 2015). 334: 296: 290: 284: 29: 330:(at 25 Â°C , 100 kPa). 302: 278: 1: 552:10.1016/s0076-6879(02)52003-6 822:10.1097/RLU.0000000000003914 499:Seminars in Nuclear Medicine 445:10.1016/j.ijrobp.2005.05.068 395:positron emission tomography 667:Journal of Nuclear Medicine 931: 910:Diagnostic medical imaging 871:10.1186/s13550-020-00689-z 15: 809:Clinical Nuclear Medicine 772:10.1007/s00259-017-3857-3 725:10.1007/s00259-014-2818-3 680:10.2967/jnumed.108.053785 597:10.1007/s00259-002-1037-5 324: 265: 245: 220: 70: 62: 42: 37: 28: 640:10.1089/cbr.2011.1130 411:head and neck cancer 44:Preferred IUPAC name 16:For other uses, see 320: g·mol 25: 357:Infobox references 23: 561:978-0-12-182255-2 365:Chemical compound 363: 362: 189:CompTox Dashboard 112:Interactive image 922: 894: 893: 883: 873: 849: 843: 842: 824: 800: 794: 793: 783: 751: 745: 744: 707: 701: 700: 682: 658: 652: 651: 623: 617: 616: 580: 574: 573: 539: 533: 532: 522: 490: 484: 483: 463: 457: 456: 428: 347: 341: 338: 337: 319: 304: 298: 292: 286: 280: 273:Chemical formula 213: 212: 197: 195: 179: 159: 148: 134: 114: 90: 65:NSC-684681; EF-5 52:-imidazol-1-yl)- 33: 26: 930: 929: 925: 924: 923: 921: 920: 919: 915:Nitroimidazoles 900: 899: 898: 897: 858:EJNMMI Research 851: 850: 846: 815:(12): 952–957. 802: 801: 797: 753: 752: 748: 719:(11): 2042–50. 709: 708: 704: 673:(12): 1944–51. 660: 659: 655: 625: 624: 620: 582: 581: 577: 562: 541: 540: 536: 492: 491: 487: 468:Cancer Research 465: 464: 460: 430: 429: 425: 420: 366: 359: 354: 353: 352:  ?) 343: 339: 335: 331: 317: 307: 301: 295: 289: 283: 275: 261: 258: 253: 252: 241: 238: 237: 234: 228: 227: 216: 198: 191: 182: 162: 149: 137: 117: 104: 93: 80: 66: 58: 57: 21: 12: 11: 5: 928: 926: 918: 917: 912: 902: 901: 896: 895: 844: 795: 766:(2): 161–169. 746: 702: 653: 618: 575: 560: 534: 485: 474:(23): 5721–6. 458: 422: 421: 419: 416: 373:nitroimidazole 364: 361: 360: 355: 333: 332: 328:standard state 325: 322: 321: 315: 309: 308: 305: 299: 293: 287: 281: 276: 271: 268: 267: 263: 262: 260: 259: 256: 248: 247: 246: 243: 242: 240: 239: 235: 232: 231: 223: 222: 221: 218: 217: 215: 214: 206:DTXSID10165114 201: 199: 187: 184: 183: 181: 180: 172: 170: 164: 163: 161: 160: 152: 150: 142: 139: 138: 136: 135: 127: 125: 119: 118: 116: 115: 107: 105: 98: 95: 94: 92: 91: 83: 81: 76: 73: 72: 68: 67: 64: 60: 59: 47: 46: 40: 39: 35: 34: 13: 10: 9: 6: 4: 3: 2: 927: 916: 913: 911: 908: 907: 905: 891: 887: 882: 877: 872: 867: 863: 859: 855: 848: 845: 840: 836: 832: 828: 823: 818: 814: 810: 806: 799: 796: 791: 787: 782: 777: 773: 769: 765: 761: 757: 750: 747: 742: 738: 734: 730: 726: 722: 718: 714: 706: 703: 698: 694: 690: 686: 681: 676: 672: 668: 664: 657: 654: 649: 645: 641: 637: 633: 629: 622: 619: 614: 610: 606: 602: 598: 594: 591:(2): 259–66. 590: 586: 579: 576: 571: 567: 563: 557: 553: 549: 545: 538: 535: 530: 526: 521: 516: 512: 508: 505:(2): 163–76. 504: 500: 496: 489: 486: 481: 477: 473: 469: 462: 459: 454: 450: 446: 442: 438: 434: 427: 424: 417: 415: 412: 406: 404: 400: 396: 392: 389: 385: 380: 378: 374: 370: 358: 351: 346: 329: 323: 316: 314: 311: 310: 277: 274: 270: 269: 264: 255: 251: 244: 230: 226: 219: 211: 207: 203: 202: 200: 190: 186: 185: 178: 174: 173: 171: 169: 166: 165: 158: 154: 153: 151: 145: 141: 140: 133: 129: 128: 126: 124: 121: 120: 113: 109: 108: 106: 102: 97: 96: 89: 85: 84: 82: 79: 75: 74: 69: 61: 55: 51: 45: 41: 36: 32: 27: 19: 861: 857: 847: 812: 808: 798: 763: 759: 749: 716: 712: 705: 670: 666: 656: 634:(7): 412–9. 631: 627: 621: 588: 584: 578: 543: 537: 502: 498: 488: 471: 467: 461: 439:(3): 922–7. 436: 432: 426: 407: 399:brain tumors 388:radiolabeled 381: 368: 367: 71:Identifiers 63:Other names 53: 49: 48:2-(2-Nitro-1 377:etanidazole 266:Properties 88:152721-37-4 904:Categories 864:(1): 103. 418:References 391:derivative 313:Molar mass 177:383HJ2T87O 123:ChemSpider 99:3D model ( 78:CAS Number 831:1536-0229 403:treatment 890:32910291 839:34619699 790:29075831 733:24898846 697:16561341 689:18997048 648:22897720 613:22002592 605:12552344 570:12125356 529:25704388 453:16458778 24:18F-EF5 881:7483702 781:5745570 741:6276936 520:4365940 480:8242628 350:what is 348: ( 318:302.161 144:PubChem 888:  878:  837:  829:  788:  778:  739:  731:  695:  687:  646:  611:  603:  568:  558:  527:  517:  478:  451:  345:verify 342:  250:SMILES 157:389053 132:344807 38:Names 737:S2CID 693:S2CID 609:S2CID 371:is a 225:InChI 101:JSmol 886:PMID 835:PMID 827:ISSN 786:PMID 729:PMID 685:PMID 644:PMID 601:PMID 566:PMID 556:ISBN 525:PMID 476:PMID 449:PMID 168:UNII 18:EF-5 876:PMC 866:doi 817:doi 776:PMC 768:doi 721:doi 675:doi 636:doi 593:doi 548:doi 515:PMC 507:doi 441:doi 369:EF5 194:EPA 147:CID 906:: 884:. 874:. 862:10 860:. 856:. 833:. 825:. 813:46 811:. 807:. 784:. 774:. 764:45 762:. 758:. 735:. 727:. 717:41 715:. 691:. 683:. 671:49 669:. 665:. 642:. 632:27 630:. 607:. 599:. 589:30 587:. 564:. 554:. 523:. 513:. 503:45 501:. 497:. 472:53 470:. 447:. 437:64 435:. 405:. 892:. 868:: 841:. 819:: 792:. 770:: 743:. 723:: 699:. 677:: 650:. 638:: 615:. 595:: 572:. 550:: 531:. 509:: 482:. 455:. 443:: 386:- 384:F 340:Y 306:3 303:O 300:4 297:N 294:5 291:F 288:7 285:H 282:8 279:C 196:) 192:( 103:) 54:N 50:H 20:.

Index

EF-5

Preferred IUPAC name
CAS Number
152721-37-4
JSmol
Interactive image
ChemSpider
344807
PubChem
389053
UNII
383HJ2T87O
CompTox Dashboard
DTXSID10165114
Edit this at Wikidata
InChI
SMILES
Chemical formula
Molar mass
standard state
verify
what is
Infobox references
nitroimidazole
etanidazole
F
radiolabeled
derivative
positron emission tomography

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