Structure via PubChem · Public domain (PubChem)
ethinylestradiol
Sign in to saveAlso known as 17α-ethynylestradiol, ethinyl estradiol, 17alpha-Ethinyl estradiol, ethinyloestradiol, 17-ethinyl-3,17-oestradiol, 17-ethinylestradiol, 17-ethinyl-3,17-estradiol
Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. Ethinylestradiol is widely used for various indications such as the treatment of menopausal symptoms, gynecological disorders, and certain hormone-sensitive cancers. It is usually taken by mouth but is also used as a patch and vaginal ring.
Key facts
- Drug.Verifiedfields
- verified
- Drug.Watchedfields
- verified
- Drug.verifiedrevid
- 458286647
- Drug.image
- Ethinylestradiol.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 235
- Drug.image2
- Ethinylestradiol molecule ball.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 235
- Drug.MedlinePlus
- a604032
- Drug.routes_of_administration
- By mouth, transdermal, vaginal
- Drug.class
- Estrogen
- Drug.ATC_prefix
- G03
- Drug.ATC_suffix
- CA01
- Drug.legal_status
- Rx-only
- Drug.bioavailability
- 38–48%
- Drug.protein_bound
- 97–98% (to albumin; is not bound to )
- Drug.metabolism
- Liver (primarily CYP3A4)
via Wikipedia infobox
Chemical data
- Formula
- C20H24O2
- Molecular weight
- 296.4 g/mol
- IUPAC name
- (8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
- SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)O
- InChIKey
- BFPYWIDHMRZLRN-SLHNCBLASA-N
- XLogP
- 3.7
- Polar surface area
- 40.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
14,622 papers- Low-dose ethinylestradiol/levonorgestrel.Drugs · 2005
- Ethinylestradiol/dienogest in oral contraception.Drugs · 2010
- Ethinylestradiol/Chlormadinone acetate: dermatological benefits.American journal of clinical dermatology · 2011
- Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception.Treatments in endocrinology · 2003
- Ethinylestradiol/drospirenone: a review of its use as an oral contraceptive.Treatments in endocrinology · 2003
via PubMed
Wikidata facts
- Mass
- 296.178
Show 5 more facts
- chemical formula
- C₂₀H₂₄O₂
- Commons category
- Ethinylestradiol
- canonical SMILES
- CC12CCC3C(C1CCC2(C#C)O)CCC4=C3C=CC(=C4)O
- isomeric SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)O
- defined daily dose
- 25
via Wikidata · CC0
~52 min read
Article
31 sectionsContents
- Medical uses
- Available forms
- Contraindications
- Side effects
- Long-term effects
- Blood clots
- Cardiovascular issues
- Liver damage
- Uterine cancer
- Ecological Effects
- Overdose
- Interactions
- Pharmacology
- Pharmacodynamics
- Antiandrogenic and antigonadotropic effects
- Effects on liver protein synthesis
- Differences from estradiol
- Pharmacokinetics
- Absorption
- Distribution
- Metabolism
- Elimination
- Chemistry
- Analogues
- History
- Society and culture
- Generic names
- Brand names
- Availability
- References
- Further reading
Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. Ethinylestradiol is widely used for various indications such as the treatment of menopausal symptoms, gynecological disorders, and certain hormone-sensitive cancers. It is usually taken by mouth but is also used as a patch and vaginal ring.
The general side effects of ethinylestradiol include breast tenderness and enlargement, headache, fluid retention, and nausea among others. In males, ethinylestradiol can additionally cause breast development, feminization in general, hypogonadism, and sexual dysfunction. Rare but serious side effects include blood clots, liver damage, and cancer of the uterus.