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
ATC code	none
PubChem	CID 6291
IUPHAR/BPS	7087
DrugBank	DB01357
ChemSpider	6054
UNII	B2V233XGE7
KEGG	D00575
ChEBI	CHEBI:6784
ChEMBL	CHEMBL1201151
Synonyms	CB-8027, EE3ME, L-33355, RS-1044
Chemical data
Formula	C21H26O2
Molar 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 Key:IMSSROKUHAOUJS-MJCUULBUSA-N
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Mestranol (INN, USAN, BAN, JAN) (brand names Devocin, Ovastol, Tranel), also known as ethinyl estradiol methyl ether (EEME),^[1] is a synthetic, steroidal estrogen that has been widely used medically.^[2][3] It was employed as the estrogen component in many of the first oral contraceptives, such as mestranol/noretynodrel (brand names Enovid, Enavid),^[4] and is still in use today. It was also a component of Ortho-Novin, Femigen, and Norbiogest.^[2] In addition to its use as an oral contraceptive, mestranol has been used as a component of hormone replacement therapy.^[3]

Mestranol is the 3-methyl ether of ethinyl estradiol,^[2] 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).^[5]

See also

• Moxestrol
• Quinestrol

References

1. A. Labhart (6 December 2012). Clinical Endocrinology: Theory and Practice. Springer Science & Business Media. pp. 575–. ISBN 978-3-642-96158-8.
2. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 775–. ISBN 978-1-4757-2085-3.
3. I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 177–. ISBN 978-94-011-4439-1.
4. Lara Marks (2010). Sexual Chemistry: A History of the Contraceptive Pill. Yale University Press. pp. 75–. ISBN 978-0-300-16791-7.
5. Faigle, Johann W.; Schenkel, Lotte (1998). "Pharmacokinetics of estrogens and progestogens". In in Fraser, Ian S. (ed.). Estrogens and Progestogens in Clinical Practice. London: Churchill Livingstone. pp. 273–294. ISBN 0-443-04706-5.