Benzestrol
 | |
| Names | |
|---|---|
| IUPAC name
p-[1,2-Diethyl-3-(p-hydroxyphenyl)butyl]phenol | |
| Systematic IUPAC name
4,4'-(3-Ethyl-2,4-hexanediyl)diphenol | |
| Other names
3-Ethyl-2,4-bis(p-hydroxyphenyl)hexane; 4,4'-(1,2-Diethyl-3-methyl-1,3-propanediyl)bisphenol; 4,4'-(1,2-Diethyl-3-methyltrimethylene)diphenol; 4,4'-(3-Ethylhexane-2,4-diyl)diphenol; Ocestrol; Chemestrogen | |
| Identifiers | |
| 85-95-0 | |
| 2139461 | |
| ChEMBL | ChEMBL2104644 |
| ChemSpider | 6566 |
| Jmol interactive 3D | Image |
| PubChem | 6827 |
| |
| |
| Properties | |
| C20H26O2 | |
| Molar mass | 298.43 g·mol−1 |
| Density | 1.063g/cm3[1] |
| Melting point | 164 °C (327 °F; 437 K) |
| Vapor pressure | 0 mmHg @ 25°C |
| Hazards | |
| Flash point | 192.811 °C (379.060 °F; 465.961 K) |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Benzestrol (INN, BAN) (brand names Chemestrogen, Ocestrol, Octestrol, Octoestrol, Octofollin) is a synthetic, non-steroidal estrogen of the stilbestrol group that was formerly used medically but has since been discontinued.[2][3][4] The stilbestrol estrogens, the most well-known of which is diethylstilbestrol (DES) were used extensively in the mid-1900s and were finally banned by the FDA due to them causing tumors in the children of women who used them.[5]
Uses
Benzestrol and other stilbestrol were used as synthetic estrogens in order to prevent premature births.[5] Based on the idea that premature births happened because the mother did not produce enough estrogen on her own, doctors prescribed benzestrol to mothers in order to increase their estrogen levels.
Studies have been done in the past on normal, mature and castrate female rats. Benzestrol produced the same type of estrus in the castrate rat when injected at 0.8 to 1.0 micrograms as when the rat was injected with 2.0 to 2.5 micrograms of estrone.[6] This is significant because less benzestrol could be used to produce the same effect as estrone in increasing estrogen production. It has been used in the past as a nonsteroidal estrogen antagonist.
History
Benzestrol is a drug in the stilbestrol family of estrogens. These drugs were first produced in the late 1930s. In 1953, experiments began on benzestrol and other stilbestrols to see if they actually helped stop premature births. This study in 1953 found that benzestrol did not in fact help stop premature births.[5] A study in 1971 found that benzestrol was the cause of a rare vaginal cancer in girls and women whose mothers had been on benzestrol while pregnant.[5]
See also
References
- ↑ "CAS". Retrieved 15 November 2012.
- ↑ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 133–. ISBN 978-1-4757-2085-3.
- ↑ I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 47–. ISBN 978-94-011-4439-1.
- ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 106–. ISBN 978-3-88763-075-1.
- 1 2 3 4 "DES History". CDC. Retrieved 2012-12-17.
- ↑ Stebbins, R.B.; Blanchard, E.W. (1945). "The Effects of a New Synthetic Estrogen, Benzestrol Upon the Hematopoietic System in the Rat". Endocrinology 36 (5): 305. doi:10.1210/endo-36-5-305.
| ||||||||||||||||||||||||||||||||||||||||||||||||
This article is issued from Wikipedia - version of the Tuesday, January 05, 2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.