Structure via PubChem · Public domain (PubChem)
mestranol
Sign in to saveAlso known as EE3-ME, 17-ethynyl-3-methoxyoestra-1(10),2,4-trien-17beta-ol, (+)-17alpha-Ethynyl-17beta-hydroxy-3-methoxy-1,3,5(10)-oestratriene, (+)-17alpha-Ethynyl-17beta-hydroxy-3-methoxy-1,3,5(10)-estratriene, 3-Methoxy-17alpha-ethynylestradiol, Ethynylestradiol 3-methyl ether, 3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17beta-ol
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. It is formulated in combination with a progestin and is not available alone. It is taken by mouth.
Key facts
- Drug.O
- 2
- Drug.Verifiedfields
- verified
- Drug.Watchedfields
- verified
- Drug.verifiedrevid
- 462249106
- Drug.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
- Drug.image
- Mestranol.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 225px
- Drug.image2
- Mestranol molecule ball.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 250px
- Drug.tradename
- Enovid, Norinyl, Ortho-Novum, others
- Drug.MedlinePlus
- a601050
- Drug.legal_status
- Rx-only
- Drug.routes_of_administration
- By mouth
- Drug.class
- Estrogen; Estrogen ether
- Drug.metabolites
- Ethinylestradiol
- Drug.elimination_half life
- Mestranol: 50 min: 7–36 hours
via Wikipedia infobox
Chemical data
- Formula
- C21H26O2
- Molecular weight
- 310.4 g/mol
- 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
- SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OC
- InChIKey
- IMSSROKUHAOUJS-MJCUULBUSA-N
- XLogP
- 4
- Polar surface area
- 29.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1961
- Admin. routes
- oral
via ChEMBL · EBI
Research
2,939 papers- Mestranol.IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans · 1979
- Lumi-mestranol and epi-lumi-mestranol.Steroids · 1979
- [Mestranol Spofa].Ceskoslovenska farmacie · 1966
- MESTRANOL IN OVULATION SUPPRESSION.Fertility and sterility · 1965
- Norethynodrel-mestranol and thyroid function.The Journal of clinical endocrinology and metabolism · 1966
via PubMed
Wikidata facts
- Mass
- 310.19328
- Has use
- medication
Show 7 more facts
- chemical formula
- C₂₁H₂₆O₂
- subject has role
- carcinogen
- canonical SMILES
- CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)OC
- isomeric SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)OC
- World Health Organisation international non-proprietary name
- mestranol
- found in taxon
- Cunninghamella elegans
- Commons category
- Mestranol
via Wikidata · CC0
~6 min read
Encyclopedic overview
12 sectionsContents
- Medical uses
- Side effects
- Pharmacology
- Chemistry
- History
- Society and culture
- Generic names
- Brand names
- Availability
- Research
- Environmental presence
- References
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. It is formulated in combination with a progestin and is not available alone. It is taken by mouth.
Side effects of mestranol include nausea, breast tension, edema, and breakthrough bleeding among others. It is an estrogen, or an agonist of the estrogen receptors, the biological target of estrogens like estradiol. Mestranol is a prodrug of ethinylestradiol in the body.
Excerpted from Wikipedia’s “mestranol” article, available under the CC BY-SA 4.0 licence.
Gallery (2)
Available in 9 languages
via Wikidata sitelinks · CC0