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| Clinical data | |
|---|---|
| Trade names | Depot-Ostromon; Depot-Oestromon; Depot-Cyren; Synthila |
| Other names | Dianisylhexene; 4,4'-Dimethoxy-α,α'-diethylstilbene; Diethylstilbestrol dimethyl ether; Dimethoxydiethylstilbestrol; (E)-4,4'-(1,2-Diethylethylene)dianisole |
| Drug class | Nonsteroidal estrogen; Estrogen ether |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.004.542 |
| Chemical and physical data | |
| Formula | C20H24O2 |
| Molar mass | 296.410 g·mol−1 |
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Dimestrol (brand names Depot-Cyren, Depot-Oestromon), also known as dianisylhexene, 4,4'-dimethoxy-α,α'-diethylstilbene, diethylstilbestrol dimethyl ether, and dimethoxydiethylstilbestrol, is a synthetic nonsteroidal estrogen of the stilbestrol group which is related to diethylstilbestrol.[1][2] It has been used clinically as a hormonal therapy in cases of delayed female puberty, hypogonadism, menopausal, and postmenopausal symptoms. It is known to induce the development of female secondary sexual characteristics in the case of female delayed puberty or hypogonadism.[3] The drug has also been used as a growth promoter in livestock.[4][5]
DES is a known endocrine disrupting chemical. Molecularly, it is known to increase the risk of aneuploidy via interference with microtubule assembly.[6]
Prior to the 1950s, DES was widely prescribed to pregnant women to prevent miscarriage and preterm labor. A study released in the 1950s found that women who were exposed to DES were at increased risk for cervical and vaginal clear cell adenocarcinoma. Shortly after this finding, the FDA discouraged the prescription of DES to pregnant women. Children were also affected by the maternal use of DES during their gestation. Study findings showed that daughters were more likely to develop fertility complications such as premature delivery, neonatal death, miscarriage, ectopic pregnancy, stillbirth, infertility, and preeclampsia. DES exposed sons may also experience genital abnormalities but no conclusive increased risk of infertility.[7]
In the case of suspected or known exposure to DES before, women are encouraged to receive pelvic examinations, PAP tests, biopsies, and breast examinations. Men should receive routine examinations from their physician in the case of suspected or potential exposure.[7]
The medication has a long duration of action of 6 weeks given by intramuscular injection.[8]
| Estrogen | Form | Major brand name(s) | EPD (14 days) | Duration | |
|---|---|---|---|---|---|
| Diethylstilbestrol (DES) | Oil solution | Metestrol | 20 mg | 1 mg ≈ 2–3 days; 3 mg ≈ 3 days | |
| Diethylstilbestrol dipropionate | Oil solution | Cyren B | 12.5–15 mg | 2.5 mg ≈ 5 days | |
| Aqueous suspension | ? | 5 mg | ? mg = 21–28 days | ||
| Dimestrol (DES dimethyl ether) | Oil solution | Depot-Cyren, Depot-Oestromon, Retalon Retard | 20–40 mg | ? | |
| Fosfestrol (DES diphosphate)a | Aqueous solution | Honvan | ? | <1 day | |
| Dienestrol diacetate | Aqueous suspension | Farmacyrol-Kristallsuspension | 50 mg | ? | |
| Hexestrol dipropionate | Oil solution | Hormoestrol, Retalon Oleosum | 25 mg | ? | |
| Hexestrol diphosphatea | Aqueous solution | Cytostesin, Pharmestrin, Retalon Aquosum | ? | Very short | |
| Note: All by intramuscular injection unless otherwise noted. Footnotes: a = By intravenous injection. Sources: See template. | |||||
Synthesis
Ex 7: The action of titanium(III) chloride and lithium aluminium hydride on 4'-methoxypropiophenone [121-97-1] causes a McMurry reaction in 85% yield.
Ex 8: The action of titanium(IV) chloride and zinc dust on 4'-methoxypropiophenone causes a McMurry reaction in 91% yield.
See also
References
- ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 396. ISBN 978-1-4757-2085-3.
- ^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 1324–. ISBN 978-0-8155-1856-3.
- ^ Soviet Genetics. Consultants Bureau. 1982.
- ^ National Research Council (U.S.). Committee on Animal Nutrition (1953). Hormonal Relationships and Applications in the Production of Meats, Milk, and Eggs: A Report of the Committee on Animal Nutrition. National Academies. pp. 5–13. ISBN 9780598358813. NAP:14582.
{{cite book}}: ISBN / Date incompatibility (help) - ^ "Diethylstilbestrol". MeSH. NCBI.
- ^ Sakakibara Y, Saito I, Ichinoseki K, Oda T, Kaneko M, Saitô H, et al. (August 1991). "Effects of diethylstilbestrol and its methyl ethers on aneuploidy induction and microtubule distribution in Chinese hamster V79 cells". Mutation Research. 263 (4): 269–76. doi:10.1016/0165-7992(91)90012-S. PMID 1861692.
- ^ a b "Diethylstilbestrol (DES) and Cancer". 2011-10-05.
- ^ Kahr H (8 March 2013). Konservative Therapie der Frauenkrankheiten: Anzeigen, Grenzen und Methoden Einschliesslich der Rezeptur. Springer-Verlag. pp. 19–20. ISBN 978-3-7091-5694-0.
- ^ John E. McMurry, U.S. patent 4,225,734 (1980 to The Regents Of The University Of California).
- ^ McMurry, John E.; Fleming, Michael P.; Kees, Kenneth L.; Krepski, Larry R. (1978). "Titanium-induced reductive coupling of carbonyls to olefins". The Journal of Organic Chemistry 43 (17): 3255–3266. doi:10.1021/jo00411a002.
