(2R*,3S*)-1-[125I]Iodo-2,3-bis(4-hydroxyphenyl)pentane ([125I]Iodonorhexestrol) and (2R*,3S*)-1-[77Br]Bromo-2,3-bis(4-hydroxyphenyl)pentane ([77Br]Bromonorhexestrol), Two γ-Emitting Estrogens That Show Receptor-Mediated Uptake by Target Tissues in Vivo

Journal of Medicinal Chemistry

Volumn 25, Issue 11, 1982, Pages 1307-1312

  Landvatter, Scott W ^a,c   Katzenellenbogen, John A ^a,c   McElvany, Karen D ^b,c   Welch, Michael J ^b,c  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c LOS ALAMOS NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; BROMONORHEXESTROL; DIAGNOSTIC AGENT; DRUG DERIVATIVE; ESTROGEN DERIVATIVE; ESTROGEN RECEPTOR; HEXESTROL; IODONORHEXESTROL; RADIOACTIVE IODINE; RADIOISOTOPE; ESTRADIOL; ESTRADIOL DERIVATIVE;

ANIMAL; ARTICLE; DRUG STABILITY; FEMALE; IN VITRO STUDY; ISOTOPE LABELING; METABOLISM; RAT; SYNTHESIS; TIME; TISSUE DISTRIBUTION; 16ALPHA IODOESTRADIOL I 125; ANIMAL EXPERIMENT; BROMONORHEXESTROL BR 77; DRUG ACCUMULATION; DRUG ANALYSIS; DRUG ANTAGONISM; DRUG BLOOD LEVEL; DRUG DISTRIBUTION; DRUG IDENTIFICATION; DRUG METABOLISM; DRUG SYNTHESIS; DRUG TISSUE LEVEL; DRUG UPTAKE; ENDOCRINE SYSTEM; FEMALE GENITAL SYSTEM; INFRARED SPECTROMETRY; INTRAVENOUS DRUG ADMINISTRATION; IODONORHEXESTROL I 125; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PHARMACOKINETICS; RADIOCHROMATOGRAPHY; THIN LAYER CHROMATOGRAPHY; THYROID GLAND; UTERUS;

ANIMAL; BROMINE; DRUG STABILITY; ESTROGENS, SYNTHETIC; FEMALE; HEXESTROL; IN VITRO; IODINE RADIOISOTOPES; ISOTOPE LABELING; RADIOISOTOPES; RATS; RECEPTORS, ESTROGEN; SUPPORT, U.S. GOV'T, NON-P.H.S.; SUPPORT, U.S. GOV'T, P.H.S.; TIME FACTORS; TISSUE DISTRIBUTION;

EID: 0020333288     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00353a007     Document Type: Article

References (25)

1. Allegra, J. C.; Lippman, M. E.; Thompson, E. B.; Simon, R.; Barlock, A.; Green, L.; Huff, K. K.; Do, H. M. T.; Aitken, S. C. Cancer Res. 1979, 39, 1447.
2. Thompson, E. B.; Lippman, M. E., Eds. “Steroid Receptors and the Management of Cancer”; CRC Press: Boca Raton, FL, 1979; Vol 1.
3. Chamness, G. C.; Horwitz, K. B. In “Receptors and Hormones Action II”; O'Malley, B. W.; Birnbaumer L., Eds.; Academic Press: New York, 1978; pp 401–441.
4. Folca, P. J.; Glascock, R. F.; Irvine, W. T., Lancet 1961, 795.
5. Desphande, N.; Jensen, V.; Bulbrook, R. D.; Berne, T.; Ellis, F. Steroids 1967, 10, 219.
6. Pearlman W. H.; DeHertogh, R.; Lammas, K. R.; Pearlman, M. R. J. J. Clin. Endocrinol. 1969, 29, 707.
7. James, F.; James, V. H. T.; Carter, A. E.; Irvine, W. T. Cancer Res. 1971, 31, 1268.
8. Katzenellenbogen, J. A.; Heiman, D. F.; Carlson, K. E.; Lloyd, J. E. In “Receptor-Binding Radiotracers”, Eckelman, W. C., Ed.; CRC Press, Boca Raton, FL, 1982, Vol. I, Chapter 6, pp 93–126.
9. Katzenellenbogen, J. A.; Senderoff, S. G.; McElvany, K. D.; O'Brien H. A., Jr.; Welch, M. J. J. Nucl. Med. 1981, 22, 42.
10. McElvany, K. D.; Katzenellenbogen, J. A.; Shafer, K. E.; Siegel, B. A.; Senderoff, S. G.; Welch, M. J. J. Nucl. Med. 1982, 23, 425.
11. Katzenellenbogen, J. A.; McElvany, K. D.; Senderoff, S. G.; Carlson, K. E.; Landvatter, S. W.; Welch, M. J. J. Nucl. Med. 1982, 23, 411.
12. Senderoff, S. G.; McElvany, K. D.; Carlson, K. E.; Heiman, D. F.; Katzenellenbogen, J. A.; Welch, M. J. Int. J. Appl. Radiat. Isot., in press.
13. Heiman, D. F.; Senderoff, S. G.; Katzenellenbogen, J. A.; Neeley, R. J. J. Med. Chem. 1980, 23, 994.
14. Goswami, R.; Harsy, S. G.; Heiman, D. F.; Katzenellenbogen, J. A. J. Med. Chem. 1980, 23, 1002.
15. Landvatter, S. W.; Katzenellenbogen, J. A. Mol. Pharmacol. 1981, 20, 43.
16. Corey, E. J.; Katzenellenbogen, J. A.; Posner, G. H. J. Am. Chem. Soc. 1967, 89, 4245. Failure to use methoxide results in only a 4% yeild of 3; the rest of the material undergoes deprotection.
17. Baird, R.; Winstein, S. J. Am. Chem. Soc. 1963, 85, 567.
18. Wayforth, H. B. “Experimental and Surgical Technique in the Rat”; Academic Press: London, 1980; p 244.
19. McElvany, K. D.; Carlson, K. E.; Welch, M. J.; Senderoff, S. G.; Katzenellenbogen, J. A. J. Nucl. Med. 1982, 23, 420.
20. Hochberg, R. B. Science 1979, 205, 1138.
21. Hochberg, R. B.; Rosner, W., Proc. Natl. Acad. Sci. U.S.A. 19808 77, 328.
22. Nicholson, J. P.; Zilva, F. Clin. Sci. 1960, 19, 391.
23. Landvatter, S. W.; Katzenellenbogen, J. A. J. Med. Chem., previous paper in this issue.
24. Burdon, J.; Farazmand, I.; Stacey, M.; Tatlow, J. C. J. Chem. Soc. 1957, 2574.
25. Grant, P. M.; Whipple, R. E.; Barnes, J. W.; Bentley, G. E.; Wanek, P. M.; O'Brien, H. A., Jr. J. Inorg. Nucl. Chem. 1981, 43, 2217.