4-Fluoroestradiol

4-Fluoroestradiol
Clinical data
Other names	4-FE2; 4-F-17β-E2; 4-Fluoro-17β-estradiol; 4-Fluoroestra-1,3,5-(10)-triene-3,17β-diol; NSC-94528
Drug class	Estrogen
Identifiers
	IUPAC name (8R,9S,13S,14S,17S)-4-fluoro-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol;
CAS Number	1881-37-4;
PubChem CID	10085622;
ChemSpider	8261159;
ChEMBL	ChEMBL1627337;
CompTox Dashboard (EPA)	DTXSID20940297 ;
Chemical and physical data
Formula	C18H23FO2
Molar mass	290.378 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=C3C=CC(=C4F)O;
	InChI InChI=1S/C18H23FO2/c1-18-9-8-11-10-4-6-15(20)17(19)13(10)3-2-12(11)14(18)5-7-16(18)21/h4,6,11-12,14,16,20-21H,2-3,5,7-9H2,1H3/t11-,12-,14+,16+,18+/m1/s1; Key:QZFXMXJXAUMHQR-ZHIYBZGJSA-N;

4-Fluoroestradiol (4-FE2) is a synthetic estrogen and a derivative of estradiol which was never marketed.^[1] It is specifically the 4-fluoro analogue of estradiol.^[1] 4-Fluoroestradiol has 180 ± 43% of the affinity of estradiol for the estrogen receptor of rat uterine cytosol and shows potent uterotrophic activity similar to that of estradiol in mice and rats.^[1]^[2] It has been labeled with fluorine-18 (¹⁸F) for potential use in medical imaging.^[3]^[4]^[5]

v
t
e
Selected biological properties of endogenous estrogens in rats
Estrogen	ERTooltip Estrogen receptor RBATooltip relative binding affinity (%)	Uterine weight (%)	Uterotrophy	LHTooltip Luteinizing hormone levels (%)	SHBGTooltip Sex hormone-binding globulin RBATooltip relative binding affinity (%)
Control	–	100	–	100	–
Estradiol (E2)	100	506 ± 20	+++	12–19	100
Estrone (E1)	11 ± 8	490 ± 22	+++	?	20
Estriol (E3)	10 ± 4	468 ± 30	+++	8–18	3
Estetrol (E4)	0.5 ± 0.2	?	Inactive	?	1
17α-Estradiol	4.2 ± 0.8	?	?	?	?
2-Hydroxyestradiol	24 ± 7	285 ± 8	+^b	31–61	28
2-Methoxyestradiol	0.05 ± 0.04	101	Inactive	?	130
4-Hydroxyestradiol	45 ± 12	?	?	?	?
4-Methoxyestradiol	1.3 ± 0.2	260	++	?	9
4-Fluoroestradiol^a	180 ± 43	?	+++	?	?
2-Hydroxyestrone	1.9 ± 0.8	130 ± 9	Inactive	110–142	8
2-Methoxyestrone	0.01 ± 0.00	103 ± 7	Inactive	95–100	120
4-Hydroxyestrone	11 ± 4	351	++	21–50	35
4-Methoxyestrone	0.13 ± 0.04	338	++	65–92	12
16α-Hydroxyestrone	2.8 ± 1.0	552 ± 42	+++	7–24	<0.5
2-Hydroxyestriol	0.9 ± 0.3	302	+^b	?	?
2-Methoxyestriol	0.01 ± 0.00	?	Inactive	?	4
Notes: Values are mean ± SD or range. ER RBA = Relative binding affinity to estrogen receptors of rat uterine cytosol. Uterine weight = Percentage change in uterine wet weight of ovariectomized rats after 72 hours with continuous administration of 1 μg/hour via subcutaneously implanted osmotic pumps. LH levels = Luteinizing hormone levels relative to baseline of ovariectomized rats after 24 to 72 hours of continuous administration via subcutaneous implant. Footnotes: ^a = Synthetic (i.e., not endogenous). ^b = Atypical uterotrophic effect which plateaus within 48 hours (estradiol's uterotrophy continues linearly up to 72 hours). Sources: See template.

References

^ ^a ^b ^c Martucci CP (July 1983). "The role of 2-methoxyestrone in estrogen action". Journal of Steroid Biochemistry. 19 (1B): 635–638. doi:10.1016/0022-4731(83)90229-7. PMID 6310247.
^ Longcope C, Rafkind I, Arunachalam T, Caspi E (September 1983). "Biological activities of 4-fluoro estrogen analogues". Journal of Steroid Biochemistry. 19 (3): 1325–1328. doi:10.1016/0022-4731(83)90158-9. PMID 6621038.
^ Eakins MN, Palmer AJ, Waters SL (November 1979). "Studies in the rat with 18F-4-fluoro-oestradiol and 18F-4-fluoro-oestrone as potential prostate scanning agents: comparison with 125I-2-iodo-oestradiol and 125I-2,4-di-iodo-oestradiol". The International Journal of Applied Radiation and Isotopes. 30 (11): 695–700. doi:10.1016/0020-708x(79)90111-x. PMID 544526.
^ Cummins CH (June 1993). "Radiolabeled steroidal estrogens in cancer research". Steroids. 58 (6): 245–259. doi:10.1016/0039-128x(93)90069-y. PMID 8212070. S2CID 29080385.
^ Al Jasem Y, Thiemann T, Gano L, Oliveira MC (2016). "Fluorinated steroids and their derivatives". Journal of Fluorine Chemistry. 185: 48–85. doi:10.1016/j.jfluchem.2016.03.009. ISSN 0022-1139.

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[pmid6310247-1] Martucci CP (July 1983). "The role of 2-methoxyestrone in estrogen action". Journal of Steroid Biochemistry. 19 (1B): 635–638. doi:10.1016/0022-4731(83)90229-7. PMID 6310247.

[pmid6621038-2] Longcope C, Rafkind I, Arunachalam T, Caspi E (September 1983). "Biological activities of 4-fluoro estrogen analogues". Journal of Steroid Biochemistry. 19 (3): 1325–1328. doi:10.1016/0022-4731(83)90158-9. PMID 6621038.

[pmid544526-3] Eakins MN, Palmer AJ, Waters SL (November 1979). "Studies in the rat with 18F-4-fluoro-oestradiol and 18F-4-fluoro-oestrone as potential prostate scanning agents: comparison with 125I-2-iodo-oestradiol and 125I-2,4-di-iodo-oestradiol". The International Journal of Applied Radiation and Isotopes. 30 (11): 695–700. doi:10.1016/0020-708x(79)90111-x. PMID 544526.

[pmid8212070-4] Cummins CH (June 1993). "Radiolabeled steroidal estrogens in cancer research". Steroids. 58 (6): 245–259. doi:10.1016/0039-128x(93)90069-y. PMID 8212070. S2CID 29080385.

[JasemThiemann2016-5] Al Jasem Y, Thiemann T, Gano L, Oliveira MC (2016). "Fluorinated steroids and their derivatives". Journal of Fluorine Chemistry. 185: 48–85. doi:10.1016/j.jfluchem.2016.03.009. ISSN 0022-1139.

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See also

References