Dimethylstilbestrol

In today's world, Dimethylstilbestrol is a topic that has captured the attention of millions of people around the world. With its multiple facets and implications, Dimethylstilbestrol has become a key point of discussion in various fields, from politics to science, culture and society in general. Throughout history, Dimethylstilbestrol has played a crucial role in the evolution of humanity, marking important milestones and generating significant changes in the way we see and understand the world around us. In this article, we will explore the different dimensions of Dimethylstilbestrol and analyze its impact on our current reality.
Dimethylstilbestrol
Clinical data
Other namesDMS; (Ε)-α,α'-Dimethyl-4,4'-stilbenediol
Drug classNonsteroidal estrogen
Identifiers
  • 4-phenol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H16O2
Molar mass240.302 g·mol−1
3D model (JSmol)
  • C/C(=C(/C)\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)O
  • InChI=1S/C16H16O2/c1-11(13-3-7-15(17)8-4-13)12(2)14-5-9-16(18)10-6-14/h3-10,17-18H,1-2H3/b12-11+
  • Key:XPINIPXARSNZDM-VAWYXSNFSA-N

Dimethylstilbestrol (DMS) is a nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol which was never marketed.[1][2][3][4][5]: 213  It is a so-called "weak", "impeded", or "short-acting" estrogen similarly to estriol and meso-butoestrol.[6][7][8][9] The affinity of DMS for the ER was reported as about 10% of that of estradiol.[10] For comparison, diethylstilbestrol had 140% of the affinity of estradiol for the ER.[10]

The endometrial proliferation dose of DMS in women is 20 mg.[5]: 212–213  A single 12 mg intramuscular injection of DMS has a duration of approximately 12 days in humans.[5]

References

  1. ^ Pincus G (3 September 2013). "Blastocyst Development and Implantation". The Control of Fertility. Elsevier. pp. 126–. ISBN 978-1-4832-7088-3.
  2. ^ Emmens CW, Martin L (5 December 2016). "Anti-Estrogens". In Dorfman RI (ed.). Steroidal Activity in Experimental Animals and Man. Elsevier Science. pp. 83–. ISBN 978-1-4832-7299-3.
  3. ^ Hilf R, Wittliff JL (27 November 2013). "Mechanisms of Action of Estrogens". In Sartorelli AC, Johns DG (eds.). Antineoplastic and Immunosuppressive Agents. Springer Science & Business Media. pp. 110–. ISBN 978-3-642-65806-8.
  4. ^ Horwitz KB, McGuire WL (14 December 2013). "Antiestrogens: Mechanism of Action and Effects in Breast Cancer". In McGuire W (ed.). Experimental Biology. Springer Science & Business Media. pp. 169–. ISBN 978-1-4757-4673-0.
  5. ^ a b c Knörr K, Beller FK, Lauritzen C (17 April 2013). "Prinzipien der Hormonbehandlung: Die wichtigsten hormonalen Behandlungsmethoden". Lehrbuch der Gynäkologie. Springer-Verlag. ISBN 978-3-662-00942-0.
  6. ^ Katzenellenbogen BS, Iwamoto HS, Heiman DF, Lan NC, Katzenellenbogen JA (1978). "Stilbestrols and stilbestrol derivatives: estrogenic potency and temporal relationships between estrogen receptor binding and uterine growth". Molecular and Cellular Endocrinology. 10 (1): 103–113. doi:10.1016/0303-7207(78)90063-1. PMID 564791. S2CID 45882988.
  7. ^ Martin L (January 1969). "Dimethylstilbestrol and 16-oxo-estradiol: anti-estrogens or estrogens?". Steroids. 13 (1): 1–10. doi:10.1016/s0039-128x(69)80055-3. PMID 5764482.
  8. ^ Emmens CW, Cox RI, Martin L (July 1959). "Oestrogen inhibitors of the stilboestrol series". The Journal of Endocrinology. 18 (4): 372–380. doi:10.1677/joe.0.0180372. PMID 13820198.
  9. ^ Emmens CW, Cox RI (September 1958). "Dimethylstilboestrol as an oestrogen inhibitor". The Journal of Endocrinology. 17 (3): 265–271. doi:10.1677/joe.0.0170265. PMID 13587831.
  10. ^ a b Jordan VC, Lieberman ME (September 1984). "Estrogen-stimulated prolactin synthesis in vitro. Classification of agonist, partial agonist, and antagonist actions based on structure". Molecular Pharmacology. 26 (2): 279–285. CiteSeerX 10.1.1.1064.9508. PMID 6541293.