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 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] It is described as a "weak", "impeded", or "short-acting" estrogen, similarly to estriol.[6]

The endometrial proliferation dose of DMS in women is 20 mg.[7] A single 12 mg intramuscular injection of DMS has a duration of approximately 12 days in humans.[7]

References

Gregory Pincus (3 September 2013). The Control of Fertility. Elsevier. pp. 126–. ISBN 978-1-4832-7088-3.
Ralph I. Dorfman (5 December 2016). Steroidal Activity in Experimental Animals and Man. Elsevier Science. pp. 83–. ISBN 978-1-4832-7299-3.
Alan C. Sartorelli; David G. Johns (27 November 2013). Antineoplastic and Immunosuppressive Agents. Springer Science & Business Media. pp. 110–. ISBN 978-3-642-65806-8.
William McGuire (14 December 2013). Experimental Biology. Springer Science & Business Media. pp. 169–. ISBN 978-1-4757-4673-0.
Karl Knörr; Fritz K. Beller; Christian Lauritzen (17 April 2013). Lehrbuch der Gynäkologie. Springer-Verlag. pp. 213–. 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". Mol. Cell. Endocrinol. 10 (1): 103–13. doi:10.1016/0303-7207(78)90063-1. PMID 564791.
Karl Knörr; Fritz K. Beller; Christian Lauritzen (17 April 2013). Lehrbuch der Gynäkologie. Springer-Verlag. pp. 212–213. ISBN 978-3-662-00942-0.

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