Dimethylstilbestrol

Dimethylstilbestrol
Clinical data
Other names	DMS; (Ε)-α,α'-Dimethyl-4,4'-stilbenediol
Drug class	Nonsteroidal estrogen
Identifiers
	IUPAC name 4-[(E)-3-(4-hydroxyphenyl)but-2-en-2-yl]phenol;
CAS Number	552-80-7 ; 13366-36-4;
PubChem CID	3004636;
ChemSpider	2274931;
UNII	30L22Q8N9M;
KEGG	C14234;
ChEBI	CHEBI:34717;
ChEMBL	ChEMBL269003;
CompTox Dashboard (EPA)	DTXSID2022468 ;
Chemical and physical data
Formula	C16H16O2
Molar mass	240.302 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C/C(=C(/C)\C1=CC=C(C=C1)O)/C2=CC=C(C=C2)O;
	InChI 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

^ Pincus G (3 September 2013). "Blastocyst Development and Implantation". The Control of Fertility. Elsevier. pp. 126–. ISBN 978-1-4832-7088-3.
^ 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.
^ 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.
^ 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.
^ ^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.
^ 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.
^ 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.
^ 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.
^ 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.
^ ^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.

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[Pincus2013-1] Pincus G (3 September 2013). "Blastocyst Development and Implantation". The Control of Fertility. Elsevier. pp. 126–. ISBN 978-1-4832-7088-3.

[Dorfman2016-2] 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.

[SartorelliJohns2013-3] 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.

[McGuire2013-4] 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.

[KnörrBeller2013-5] 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.

[pmid564791-6] 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.

[pmid5764482-7] 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.

[pmid13820198-8] 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.

[pmid13587831-9] 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.

[pmid6541293-10] 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.

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