Mestranol

Mestranol
Clinical data
Trade names	Enovid, Norinyl, Ortho-Novum, others
Other names	Ethinylestradiol 3-methyl ether; EEME; EE3ME; CB-8027; L-33355; RS-1044; 17α-Ethynylestradiol 3-methyl ether; 17α-Ethynyl-3-methoxyestra-1,3,5(10)-trien-17β-ol; 3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17β-ol
AHFS/Drugs.com	International Drug Names
MedlinePlus	a601050
Routes of; administration	By mouth
Drug class	Estrogen; Estrogen ether
ATC code	None;
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Metabolites	Ethinylestradiol
Elimination half-life	Mestranol: 50 min; EE: 7–36 hours
Identifiers
	IUPAC name (8R,9S,13S,14S,17R)-17-ethynyl-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-ol;
CAS Number	72-33-3 ;
PubChem CID	6291;
IUPHAR/BPS	7087;
DrugBank	DB01357 ;
ChemSpider	6054 ;
UNII	B2V233XGE7;
KEGG	D00575 ;
ChEBI	CHEBI:6784 ;
ChEMBL	ChEMBL1201151 ;
CompTox Dashboard (EPA)	DTXSID0020814 ;
ECHA InfoCard	100.000.707
Chemical and physical data
Formula	C21H26O2
Molar mass	310.437 g·mol−1
3D model (JSmol)	Interactive image;
	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 ;
	(verify)

Mestranol, sold under the brand names Enovid, Norinyl, and Ortho-Novum among others, is an estrogen medication which has been used in birth control pills, menopausal hormone therapy, and the treatment of menstrual disorders.^[1]^[7]^[8]^[9] It is formulated in combination with a progestin and is not available alone.^[9] It is taken by mouth.^[1]

Side effects of mestranol include nausea, breast tension, edema, and breakthrough bleeding among others.^[10] It is an estrogen, or an agonist of the estrogen receptors, the biological target of estrogens like estradiol.^[11] Mestranol is a prodrug of ethinylestradiol in the body.^[11]

Mestranol was discovered in 1956 and was introduced for medical use in 1957.^[12]^[13] It was the estrogen component in the first birth control pill.^[12]^[13] In 1969, mestranol was replaced by ethinylestradiol in most birth control pills, although mestranol continues to be used in a few birth control pills even today.^[14]^[9] Mestranol remains available only in a few countries, including the United States, United Kingdom, Japan, and Chile.^[9]

^ ^a ^b ^c Cite error: The named reference MortonHall2012 was invoked but never defined (see the help page).
^ Cite error: The named reference RunnebaumRabe2013 was invoked but never defined (see the help page).
^ Cite error: The named reference HughesWaters2016 was invoked but never defined (see the help page).
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^ Cite error: The named reference pmid23375353 was invoked but never defined (see the help page).
^ Cite error: The named reference Shellenberger1986 was invoked but never defined (see the help page).
^ Cite error: The named reference Marks2010 was invoked but never defined (see the help page).
^ Cite error: The named reference Blum2013 was invoked but never defined (see the help page).
^ ^a ^b ^c ^d Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
^ Wittlinger H (1980). "Clinical Effects of Estrogens". Functional Morphologic Changes in Female Sex Organs Induced by Exogenous Hormones. Springer. pp. 67–71. doi:10.1007/978-3-642-67568-3_10. ISBN 978-3-642-67570-6.
^ ^a ^b Shoupe D (7 November 2007). The Handbook of Contraception: A Guide for Practical Management. Springer Science & Business Media. pp. 23–. ISBN 978-1-59745-150-5. EE is about 1.7 times as potent as the same weight of mestranol.
^ ^a ^b Cite error: The named reference Sneader2005 was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference LentzLobo2012 was invoked but never defined (see the help page).
^ Cite error: The named reference Aronson2009 was invoked but never defined (see the help page).

[MortonHall2012-1] Cite error: The named reference MortonHall2012 was invoked but never defined (see the help page).

[RunnebaumRabe2013-2] Cite error: The named reference RunnebaumRabe2013 was invoked but never defined (see the help page).

[HughesWaters2016-3] Cite error: The named reference HughesWaters2016 was invoked but never defined (see the help page).

[pmid2256522-4] Cite error: The named reference pmid2256522 was invoked but never defined (see the help page).

[pmid23375353-5] Cite error: The named reference pmid23375353 was invoked but never defined (see the help page).

[Shellenberger1986-6] Cite error: The named reference Shellenberger1986 was invoked but never defined (see the help page).

[Marks2010-7] Cite error: The named reference Marks2010 was invoked but never defined (see the help page).

[Blum2013-8] Cite error: The named reference Blum2013 was invoked but never defined (see the help page).

[Drugs.com-9] Cite error: The named reference Drugs.com was invoked but never defined (see the help page).

[Wittlinger1980-10] Wittlinger H (1980). "Clinical Effects of Estrogens". Functional Morphologic Changes in Female Sex Organs Induced by Exogenous Hormones. Springer. pp. 67–71. doi:10.1007/978-3-642-67568-3_10. ISBN 978-3-642-67570-6.

[Shoupe2007-11] Shoupe D (7 November 2007). The Handbook of Contraception: A Guide for Practical Management. Springer Science & Business Media. pp. 23–. ISBN 978-1-59745-150-5. EE is about 1.7 times as potent as the same weight of mestranol.

[Sneader2005-12] Cite error: The named reference Sneader2005 was invoked but never defined (see the help page).

[LentzLobo2012-13] Cite error: The named reference LentzLobo2012 was invoked but never defined (see the help page).

[Aronson2009-14] Cite error: The named reference Aronson2009 was invoked but never defined (see the help page).

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