Diethylstilbestrol

Structural formula
General
Non-proprietary name	Diethylstilbestrol
other names	4- [4- (4-hydroxyphenyl) hex-3-en-3-yl] phenol
Molecular formula	C 18 H 20 O 2
External identifiers / databases
EC number	200-278-5
ECHA InfoCard	100,000,253
PubChem	448537
ChemSpider	395306
DrugBank	DB00255
Wikidata	Q423989
Drug information
ATC code	G03 CB02 ; G03 CC05 ; L02 AA01 ;
Drug class	selective estrogen receptor modulators
properties
Molar mass	268.35 g mol −1
Physical state	firmly
Melting point	170-171 ° C
solubility	almost insoluble in water (12 mg l −1 at 25 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 315-319-335-350-360-410
	P: 201-261-273-305 + 351 + 338-308 + 313-501
Toxicological data	> 3000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Diethylstilbestrol ( DES ), also called diethylstilbestrol , is a synthetic drug from the group of non-steroidal , selective estrogen receptor modulators (SERM). An analogue of DES is Hexestrol . The antiestrogen DES was mainly used in the USA until the 1970s in pregnant women to prevent pregnancy complications ; the substance was banned in gynecology after it became known that it had a teratogenic effect and that, in offspring, u. a. Vaginal cancer or micropenis . Today it is estimated that 5 to 10 million women (mainly in the USA) have been treated with DES and a total of 12 long-term gynecological effects of intrauterine exposure to DES have been described, including an increased rate of premature births and miscarriages.

history

DES was first synthesized in 1938 by Edward Charles Dodds , Leon Goldberg and Robert Robinson and approved for the treatment of colpitis , relief of menopausal symptoms and breastfeeding. In 1960 it was discovered that DES worked better than androgens in the treatment of advanced breast cancer in postmenopausal women. In 1971 it was found to be a teratogen and may cause u. a. Vaginal cancer or micropenis . Due to its effect on the lining of the uterus, DES was used as a “morning-after pill” to prevent the fertilized egg from implanting, to prevent pregnancy after unprotected sexual intercourse. In the 1990s, the only recognized indications for DES treatment were advanced postmenopausal breast cancer and advanced prostate cancer . The last remaining maker of DES, Eli Lilly , stopped marketing DES in 1997.

Individual evidence

↑ ^a ^b ^c Entry on diethylstilbestrol in the ChemIDplus database of the United States National Library of Medicine (NLM)
↑ ^a ^b Data sheet Diethylstilbestrol from Sigma-Aldrich , accessed on March 25, 2011 ( PDF ).
↑ ^a ^b Diethylstilbestrol: Lifelong consequences of intra-uterine exposure . In: Deutsches Ärzteblatt . October 6, 2011. Archived from the original on December 28, 2017. Retrieved on December 27, 2017.
↑ ^a ^b ^c Laura N. Vandenberg: Fetal Origins of Adult Disease: Xenoestrogens and Breast Cancer Risk . ProQuest, 2007, ISBN 0-549-36033-6 , pp. 38 ( limited preview in Google Book search).
^ Teresa Ortiz-Gómez, María Jesús Santesmases: Gendered Drugs and Medicine: Historical and Socio-Cultural Perspectives . Ashgate Publishing, Ltd., 2014, ISBN 978-1-4094-5404-5 , pp. 26 ( limited preview in Google Book search).
^ Council on Drugs: Androgens and estrogens in the treatment of disseminated mammary carcinoma: retrospective study of nine hundred forty-four patients . In: JAMA . 172, No. 12, 1960, pp. 1271-1283.
↑ Inquiry in the German Bundestag: Risks and long-term effects of hormone treatments in gynecology, reproductive medicine and obstetrics, using the example of the hormone preparation diethylstilbestrol (DES) (November 14, 1990).
^ Susan E. Bell, DES Daughters, Embodied Knowledge, and the Transformation of Women's Health Politics in the Late Twentieth Century . Temple University Press, 2009, ISBN 978-1-59213-920-0 , pp. 180 ( limited preview in Google Book Search).

[ChemIDplus-1] Entry on diethylstilbestrol in the ChemIDplus database of the United States National Library of Medicine (NLM)

[Sigma-2] Data sheet Diethylstilbestrol from Sigma-Aldrich , accessed on March 25, 2011 ( PDF ).

[urlDiethylstilbestrolLebenslange-3] Diethylstilbestrol: Lifelong consequences of intra-uterine exposure . In: Deutsches Ärzteblatt . October 6, 2011. Archived from the original on December 28, 2017. Retrieved on December 27, 2017.

[Laura_N._Vandenberg-4] Laura N. Vandenberg: Fetal Origins of Adult Disease: Xenoestrogens and Breast Cancer Risk . ProQuest, 2007, ISBN 0-549-36033-6 , pp. 38 ( limited preview in Google Book search).

[Professor_Teresa_Ortiz-Gómez,_Dr_María_Jesús_Santesmases-5] Teresa Ortiz-Gómez, María Jesús Santesmases: Gendered Drugs and Medicine: Historical and Socio-Cultural Perspectives . Ashgate Publishing, Ltd., 2014, ISBN 978-1-4094-5404-5 , pp. 26 ( limited preview in Google Book search).

[6] Council on Drugs: Androgens and estrogens in the treatment of disseminated mammary carcinoma: retrospective study of nine hundred forty-four patients . In: JAMA . 172, No. 12, 1960, pp. 1271-1283.

[7] Inquiry in the German Bundestag: Risks and long-term effects of hormone treatments in gynecology, reproductive medicine and obstetrics, using the example of the hormone preparation diethylstilbestrol (DES) (November 14, 1990).

[Susan_E._Bell-8] Susan E. Bell, DES Daughters, Embodied Knowledge, and the Transformation of Women's Health Politics in the Late Twentieth Century . Temple University Press, 2009, ISBN 978-1-59213-920-0 , pp. 180 ( limited preview in Google Book Search).