Mestranol

Structural formula
General
Non-proprietary name	Mestranol
other names	3-methoxy-19-nor-17 α -pregna-1,3,5 (10) -trien-20-in-17 β -ol; 17 α -ethynyl-3-methoxy-1,3,5 (10) -estratriene-17 β -ol; Mestranolum ( Latin );
Molecular formula	C 21 H 26 O 2
External identifiers / databases
EC number	200-777-8
ECHA InfoCard	100,000,707
PubChem	6291
ChemSpider	6054
DrugBank	DB01357
Wikidata	Q904308
Drug information
ATC code	G03 CA10
Drug class	Estrogens
properties
Molar mass	310.43 g · mol -1
Physical state	firmly
Melting point	153-155 ° 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: 315-319-351
	P: 281-305 + 351 + 338
	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 .

[Sigma-1] Mestranol data sheet from Sigma-Aldrich , accessed on May 15, 2017 ( PDF ).

[2] 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 .