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Dimethylstilbestrol

From Wikipedia, the free encyclopedia
Chemical compound
Not to be confused withDiethylstilbestrol orDimestrol.
Pharmaceutical compound
Dimethylstilbestrol
Clinical data
Other namesDMS; (Ε)-α,α'-Dimethyl-4,4'-stilbenediol
Drug classNonsteroidal estrogen
Identifiers
  • 4-[(E)-3-(4-hydroxyphenyl)but-2-en-2-yl]phenol
CAS Number
PubChemCID
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 anonsteroidal estrogen of thestilbestrol group related todiethylstilbestrol which was never marketed.[1][2][3][4][5]: 213  It is a so-called "weak", "impeded", or "short-acting" estrogen similarly toestriol andmeso-butoestrol.[6][7][8][9] Theaffinity of DMS for the ER was reported as about 10% of that ofestradiol.[10] For comparison,diethylstilbestrol had 140% of the affinity of estradiol for the ER.[10]

Theendometrial proliferation dose of DMS in women is 20 mg.[5]: 212–213  A single 12 mgintramuscular injection of DMS has aduration of approximately 12 days in humans.[5]

Synthesis

[edit]

In the old school synthesis, reaction ofdiacetyl with 2 molecules of phenol occurs in a manner similar toBPA (acetone was used here).Pinacol rearrangement then yields thestilbenoid. What is surprising is that ifm-cresol was used instead of phenol, the resulting product had a potency 0.5 times the potency ofDES, which is remarkably potent.[11]

In the newer version of the synthesis, aMcMurry reaction (homodimerization) between on 4-Acetylanisole [100-06-1] and the appropriate choice of a reagent will yield 1,1'-(But-2-ene-2,3-diyl)bis(4-methoxybenzene) [895-37-4]. Demethylation of the two ethers then concludes the synthesis.[12][13]

References

[edit]
  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. ^abcKnörr 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. ^abJordan 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.
  11. ^Sisido, Keiiti., Nozaki, Hitosi., Iwako, Tatuo. (June 1949)."The Preparation of Synthetic Estrogens. IV. 1 Condensation of Biacetyl with Phenols".Journal of the American Chemical Society.71 (6):2037–2041.doi:10.1021/ja01174a039.
  12. ^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.
  13. ^John E. McMurry,U.S. patent 4,225,734 (1980 to The Regents Of The University Of California).
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
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