Dimestrol

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]

Not to be confused with Dimethylstilbestrol.
Dimestrol
Clinical data
Trade namesDepot-Ostromon; Depot-Oestromon; Depot-Cyren; Synthila
Other namesDianisylhexene; 4,4'-Dimethoxy-α,α'-diethylstilbene; Diethylstilbestrol dimethyl ether; Dimethoxydiethylstilbestrol; (E)-4,4'-(1,2-Diethylethylene)dianisole
Drug classNonsteroidal estrogen; Estrogen ether
Identifiers
IUPAC name
  • 1-methoxy-4-[(E)-4-(4-methoxyphenyl)hex-3-en-3-yl]benzene
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.542
Chemical and physical data
FormulaC20H24O2
Molar mass296.410 g·mol−1
3D model (JSmol)
SMILES
  • CCC(=C(CC)C1=CC=C(C=C1)OC)C2=CC=C(C=C2)OC
InChI
  • InChI=1S/C20H24O2/c1-5-19(15-7-11-17(21-3)12-8-15)20(6-2)16-9-13-18(22-4)14-10-16/h7-14H,5-6H2,1-4H3/b20-19+
  • Key:VQOAQMIKPYNCMV-FMQUCBEESA-N

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]

Parenteral potencies and durations of nonsteroidal estrogens
EstrogenFormMajor brand name(s)EPD (14 days)Duration
Diethylstilbestrol (DES)Oil solutionMetestrol20 mg1 mg ≈ 2–3 days; 3 mg ≈ 3 days
Diethylstilbestrol dipropionateOil solutionCyren B12.5–15 mg2.5 mg ≈ 5 days
Aqueous suspension ?5 mg ? mg = 21–28 days
Dimestrol (DES dimethyl ether)Oil solutionDepot-Cyren, Depot-Oestromon, Retalon Retard20–40 mg ?
Fosfestrol (DES diphosphate)aAqueous solutionHonvan ?<1 day
Dienestrol diacetateAqueous suspensionFarmacyrol-Kristallsuspension50 mg ?
Hexestrol dipropionateOil solutionHormoestrol, Retalon Oleosum25 mg ?
Hexestrol diphosphateaAqueous solutionCytostesin, Pharmestrin, Retalon Aquosum ?Very short
Note: All by intramuscular injection unless otherwise noted. Footnotes: a = By intravenous injection. Sources: See template.

See also

References
  1. 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.
  2. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 1324–. ISBN 978-0-8155-1856-3.
  3. Soviet Genetics. Consultants Bureau. 1982.
  4. 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.
  5. "Diethylstilbestrol". MeSH. NCBI.
  6. 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.
  7. "Diethylstilbestrol (DES) and Cancer". 2011-10-05.
  8. 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.
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