Mestranol
Structural formula | ||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
General | ||||||||||||||||||||||
Non-proprietary name | Mestranol | |||||||||||||||||||||
other names |
|
|||||||||||||||||||||
Molecular formula | C 21 H 26 O 2 | |||||||||||||||||||||
External identifiers / databases | ||||||||||||||||||||||
|
||||||||||||||||||||||
Drug information | ||||||||||||||||||||||
ATC code | ||||||||||||||||||||||
Drug class | ||||||||||||||||||||||
properties | ||||||||||||||||||||||
Molar mass | 310.43 g · mol -1 | |||||||||||||||||||||
Physical state |
firmly |
|||||||||||||||||||||
Melting point |
153-155 ° C |
|||||||||||||||||||||
safety instructions | ||||||||||||||||||||||
|
||||||||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Mestranol is a synthetic drug from the group of estrogens . It is a prodrug (an inactive precursor) of the frequently employed in medicaments for contraception used ethinylestradiol .
Pharmacological properties
From a chemical point of view, mestranol is the 3-methyl ether of ethinylestradiol. For the interaction with the estrogen receptor, however , the free hydroxyl group is essential, so Mestranol itself is inactive. After oral ingestion, mestranol is absorbed in the gastrointestinal tract and converted into ethinylestradiol in the liver by demethylation. The extent of this conversion is highly variable, which is why Mestranol is only rarely used today.
Clinical information
Like ethinylestradiol, mestranol can be used as an estrogenic component in combined oral contraceptives ( birth control pills ) or in preparations for hormone replacement therapy . The contraindications (contraindications), adverse effects and drug interactions are the same as for ethinylestradiol.
Finished medicinal products containing mestranol are no longer in use in most countries.
Individual evidence
- ↑ a b c Mestranol data sheet from Sigma-Aldrich , accessed on May 15, 2017 ( PDF ).
- ↑ Fotherby K. Bioavailability of orally Administered sex steroids used in oral contraception and hormone replacement therapy. In: Contraception . 1996 Aug; 54 (2): 59-69. PMID 8842581 .