Benzestrol

Benzestrol (INNTooltip International Nonproprietary Name, BANTooltip British Approved Name) (brand names Chemestrogen, Ocestrol, Octestrol, Octoestrol, Octofollin) is a synthetic nonsteroidal estrogen of the stilbestrol group which was formerly used medically but has since been discontinued.^[1][2][3] The stilbestrol estrogens, the best-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.^[4]

Benzestrol

Clinical data
Trade names	Chemestrogen, Ocestrol, Octestrol, Octoestrol, Octofollin
Drug class	Nonsteroidal estrogen
Identifiers
IUPAC name 4,4'-(3-ethylhexane-2,4-diyl)diphenol
CAS Number	85-95-0
PubChem CID	6827
ChemSpider	6566
UNII	A27512LR47
ChEBI	CHEBI:135264
ChEMBL	ChEMBL2104644
CompTox Dashboard (EPA)	DTXSID50861663
Chemical and physical data
Formula	C20H26O2
Molar mass	298.426 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC(C1=CC=C(C=C1)O)C(CC)C(C)C2=CC=C(C=C2)O
InChI InChI=InChI=1S/C20H26O2/c1-4-19(14(3)15-6-10-17(21)11-7-15)20(5-2)16-8-12-18(22)13-9-16/h6-14,19-22H,4-5H2,1-3H3 Key:DUTFBSAKKUNBAL-UHFFFAOYSA-N

Medical uses

Benzestrol and other stilbestrol were used as synthetic estrogens in order to prevent premature births.^[4] 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.^[5] 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.

Pharmacology

Pharmacodynamics

Benzestrol is described as a very potent estrogen.^[6] It is reported to have about 130% of the relative binding affinity of estradiol for the estrogen receptors.^[7]

Chemistry

Benzestrol is usually grouped with the stilbestrol estrogens. However, benzestrol is technically not a stilbestrol derivative because its central chain is elongated by one carbon. In any case, it is a very close analogue of the stilbestrol estrogens.^[8]

History

Benzestrol is a drug in the stilbestrol family of estrogens. These drugs were first produced in the late 1930s. Benzestrol itself was reported in 1946.^[1] 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.^[4] 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.^[4]

See also

• Dienestrol
• Hexestrol
• Methestrol

References

1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 133–. ISBN 978-1-4757-2085-3.
2. Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 47–. ISBN 978-94-011-4439-1.
3. "Benzestrol". Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 106–. ISBN 978-3-88763-075-1.
4. "DES History". U.S. Centers for Disease Control and Prevention. Archived from the original on 15 June 2019. Retrieved 17 December 2012.
5. Stebbins RB, Blanchard EW (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.
6. Agarwal OP (2006). "Sex hormones". Natural Products. Krishna Prakashan Media. pp. 288–. ISBN 978-81-87224-85-3.
7. Fink BE, Mortensen DS, Stauffer SR, Aron ZD, Katzenellenbogen JA (April 1999). "Novel structural templates for estrogen-receptor ligands and prospects for combinatorial synthesis of estrogens". Chemistry & Biology. 6 (4): 205–219. doi:10.1016/S1074-5521(99)80037-4. PMID 10099132.
8. Sevringhaus EL (1944). "Therapy of the Patient in the Menopause: Endocrine Methods". The Journal of Clinical Endocrinology & Metabolism. 4 (12): 597–604. doi:10.1210/jcem-4-12-597. ISSN 0021-972X.