Mestranol

Mestranol
Clinical data
Trade namesEnovid, Norinyl, Ortho-Novum, others
Other namesEthinylestradiol 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.comInternational Drug Names
MedlinePlusa601050
Routes of
administration		By mouth[1]
Drug classEstrogen; Estrogen ether
ATC code
  • None
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
MetabolitesEthinylestradiol
Elimination half-lifeMestranol: 50 min[2]
EE: 7–36 hours[3][4][5][6]
Identifiers
  • (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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.707 Edit this at Wikidata
Chemical and physical data
FormulaC21H26O2
Molar mass310.437 g·mol−1
3D model (JSmol)
  • O(c1cc4c(cc1)[C@H]3CC[C@]2([C@@H](CC[C@]2(C#C)O)[C@@H]3CC4)C)C
  • 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 checkY
  • Key:IMSSROKUHAOUJS-MJCUULBUSA-N checkY
  (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]

  1. ^ a b c Cite error: The named reference MortonHall2012 was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference RunnebaumRabe2013 was invoked but never defined (see the help page).
  3. ^ Cite error: The named reference HughesWaters2016 was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference pmid2256522 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference pmid23375353 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference Shellenberger1986 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference Marks2010 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Blum2013 was invoked but never defined (see the help page).
  9. ^ a b c d Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  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.
  11. ^ 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.
  12. ^ a b Cite error: The named reference Sneader2005 was invoked but never defined (see the help page).
  13. ^ a b Cite error: The named reference LentzLobo2012 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference Aronson2009 was invoked but never defined (see the help page).