Mestranol

Mestranol

Systematic (IUPAC) name
3-Methoxy-19-nor-17α-pregna-1,3,5(10)-trien-20-yn-17-ol
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a601050
Identifiers
CAS Number	72-33-3 Y
ATC code	none
PubChem	CID: 6291
IUPHAR/BPS	7087
DrugBank	DB01357 Y
ChemSpider	6054 Y
UNII	B2V233XGE7 Y
KEGG	D00575 Y
ChEBI	CHEBI:6784 Y
ChEMBL	CHEMBL1201151 N
Synonyms	CB-8027, EE3ME, L-33355, RS-1044
Chemical data
Formula	C21H26O2
Molecular mass	310.43 g/mol
SMILES O(c1cc4c(cc1)[C@H]3CC[C@]2([C@@H](CC[C@]2(C#C)O)[C@@H]3CC4)C)C
InChI InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1 Y Key:IMSSROKUHAOUJS-MJCUULBUSA-N Y
NY (what is this?)  (verify)

Mestranol (INN, USAN, BAN, JAN) (brand names Devocin, Ovastol, Tranel), also known as ethinyl estradiol methyl ether (EEME), is a synthetic, steroidal estrogen that has been widely used medically. It was employed as the estrogen component in many of the first oral contraceptives, such as mestranol/noretynodrel (brand names Enovid, Enavid), and is still in use today. It was also a component of Ortho-Novin, Femigen, and Norbiogest. In addition to its use as an oral contraceptive, mestranol has been used as a component of hormone replacement therapy.

Mestranol is the 3-methyl ether of ethinyl estradiol, and is a biologically inactive prodrug of ethinyl estradiol to which it is demethylated in the liver with a conversion efficiency of 70% (50 µg of mestranol is pharmacokinetically bioequivalent to 35 µg of ethinyl estradiol).

See also

• Moxestrol
• Quinestrol