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ethinyl estradiol

Trade name: Estinyl

Small moleculeapproved

Approved

Jun 25, 1943

Ethinyl estradiol is a synthetic derivative of the natural estrogen estradiol. It is one of two estrogens currently used in oral contraceptive pills. The other, mestranol, is converted to ethinyl estradiol before it is biologically active. Ethinyl estradiol and norethindrone are used together as an oral contraceptive agent. Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. This cascade is initiated by initially binding to the estrogen receptors. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH). Used for treatment of moderate to severe vasomotor symptoms associated with the menopause, female hypogonadism, prostatic carcinoma-palliative therapy of advanced disease, breast cancer, as an oral contraceptive, and as emergency contraceptive. — NCATS

Clinical trial activity

449 trials · 258 clinical orgs · 53 marketing orgs

Phase 1
166
Phase 2
151
Phase 3
110
Phase 4
76

Earliest trial started Feb 1, 1989 (NCT00191113)

Timeline

1940s

  1. Jun 1, 1943

    Schering-Plough — First NDA Organization

  2. Jun 1, 1943

    Schering-Plough — NDA Organization

  3. Jun 25, 1943

    Earliest FDA Approval

  4. Jun 25, 1943

    Schering-Plough — NDA Secondary Org

  5. Jun 25, 1943

    Schering — NDA Secondary Org

  6. Apr 13, 1944

    Organon — NDA Secondary Org

1960s

  1. Apr 16, 1968

    Wyeth — Marketing Organization

  2. Apr 16, 1968

    American Home Products — NDA Secondary Org

1970s

  1. Apr 24, 1970

    G D Searle — Marketing Organization

  2. Apr 24, 1970

    G D Searle — NDA Secondary Org

  3. Apr 30, 1973

    Allergan — NDA Secondary Org

  4. Apr 30, 1973

    Teva — NDA Secondary Org

  5. Dec 26, 1974

    Allergan — Marketing Organization

  6. Mar 17, 1975

    Cadence Pharmaceuticals — Marketing Organization

  7. Mar 17, 1975

    Cadence Pharmaceuticals — NDA Secondary Org

  8. Aug 28, 1975

    Warner Chilcott — NDA Secondary Org

  9. May 14, 1976

    Johnson and Johnson — Marketing Organization

  10. Jul 5, 1978

    Warner Chilcott — Marketing Organization

1980s

  1. Jan 11, 1982

    Johnson and Johnson — NDA Secondary Org

  2. Apr 11, 1984

    Mayne Pharma — Marketing Organization

  3. Apr 11, 1984

    Dr. Reddy's Laboratories — NDA Secondary Org

  4. Jul 18, 1986

    Pfizer — NDA Secondary Org

  5. Jan 29, 1987

    Watson Pharmaceuticals — Marketing Organization

  6. Jan 29, 1987

    Teva — Marketing Organization

  7. Dec 14, 1987

    Lupin — Marketing Organization

  8. Jan 1, 1989

    Earliest Phase 3 Sponsor(trial)

1990s

  1. Feb 28, 1992

    Barr Laboratories — Marketing Organization

  2. Jan 1, 1993

    Earliest Phase 2 Sponsor(trial)

  3. Oct 9, 1996

    SmithKline Beecham — NDA Secondary Org

  4. Jan 1, 1998

    Earliest Phase 1 Sponsor(trial)

  5. Jul 13, 1998

    Bayer — Marketing Organization

  6. Jul 13, 1998

    Bayer — NDA Secondary Org

  7. Aug 12, 1999

    Duramed Research — Marketing Organization

2000s

  1. Dec 20, 2000

    Aspen Pharmaceuticals — Marketing Organization

  2. Dec 20, 2000

    Aspen Pharmaceuticals — NDA Secondary Org

  3. Oct 3, 2001

    Organon — Marketing Organization

  4. Nov 14, 2003

    GlaxoSmithKline — NDA Secondary Org

  5. Jan 9, 2004

    Endo Pharmaceuticals — Marketing Organization

  6. Sep 1, 2009

    Amneal Pharmaceuticals — Marketing Organization

2010s

  1. Aug 3, 2010

    Leon Pharma — Marketing Organization

  2. Nov 12, 2010

    Apax Partners — Marketing Organization

  3. Mar 22, 2011

    Glenmark Pharmaceuticals — Marketing Organization

  4. Nov 6, 2012

    Vintage — Marketing Organization

  5. Dec 21, 2012

    Mylan — Marketing Organization

  6. Jul 12, 2013

    Novast Labs — Marketing Organization

  7. Apr 7, 2015

    Oc Pharma — Marketing Organization

  8. Apr 7, 2015

    Naari Pte Ltd — Marketing Organization

  9. Jul 6, 2016

    Aurobindo Pharma — Marketing Organization

  10. Sep 21, 2016

    Apotex — Marketing Organization

  11. Oct 11, 2016

    Allergan PLC (2015) — Marketing Organization

  12. Nov 22, 2016

    Accord Research — Marketing Organization

  13. Jul 18, 2017

    Pharmaceutics International, Inc. — Marketing Organization

  14. Jul 18, 2017

    Allied Pharmaceutical Services — Marketing Organization

  15. Jul 18, 2017

    Healthcare Discoveries Inc. — Marketing Organization

  16. Jul 18, 2017

    ANDA Repository — Marketing Organization

  17. Dec 22, 2017

    Jubilant Innovation Ltd. — Marketing Organization

  18. Jan 9, 2018

    Avion Pharmaceuticals — Marketing Organization

  19. Jan 9, 2018

    Avion Pharmaceuticals — NDA Secondary Org

  20. Jul 16, 2018

    Exeltis — Marketing Organization

  21. Aug 10, 2018

    TherapeuticsMD — Marketing Organization

  22. Aug 10, 2018

    Mayne Pharma — NDA Secondary Org

  23. Jan 7, 2019

    Sun Pharmaceuticals — Marketing Organization

  24. Mar 22, 2019

    Hetero Labs Ltd — Marketing Organization

2020s

  1. Feb 14, 2020

    Agile Therapeutics — NDA Secondary Org

  2. Mar 30, 2020

    Exeltis — NDA Secondary Org

  3. Dec 18, 2020

    Slayback Pharma Llc — Marketing Organization

  4. Dec 18, 2020

    Wilshire Pharmaceuticals — Marketing Organization

  5. Dec 9, 2021

    Dr. Reddy's Laboratories — Marketing Organization

  6. Sep 14, 2023

    Zydus Discovery DMCC — Marketing Organization

  7. Jul 22, 2024

    Galen — NDA Secondary Org

Indications

Approved for

Studied for

Mechanism of action

Combination products

  • annovera

    with segesterone

    Also known as segesterone acetate and ethinyl estradiol vaginal system

  • beyaz

    with drospirenone, levomefolate

    Also known as safyral, tydemy

  • demulen

    with etynodiol acetate

    Also known as kelnor, lo-malmorede, malmorede, zovia 1/35e, zovia 1/50e

  • desogen

    with desogestrel

    Also known as bekyree, cyclessa, desogestrel; ethinyl, emoquette, enskyce, isibloom, kalliga, kariva, kimidess, mircette, nuvaring, ortho-cept, pimtrea, velivet, viorele, volnea

  • loestrin fe

    with norethindrone

    Also known as alyacen, aranelle, aurovela, aurovela 24 fe, aurovela fe, balziva, blisovi 24 fe, blisovi fe, brevicon, briellyn, cyclafem, cyonanz, dasetta, estrostep, estrostep fe, femcon fe, femhrt, fyavolv, gencept, gildagia, gildess, gildess 24 fe, gildess fe, hailey, hailey fe, junel, junel fe, kaitlib fe, larin, larin 24 fe, larin fe, leribane, loestrin, loestrin 24 fe, lo larin fe, lo loestrin fe, lo minastrin fe, mibelas 24 fe, microgestin, microgestin fe, minastrin 24 fe, modicon, n.e.e, net/ee, nexesta fe, norcept-e, norethin 1/35e, norethindrone acetate and ethinyl estradiol and ethinyl estradiol and ferrous fumarate, norethindrone acetate and ethinyl estradiol and ferrous fumarate, norethindrone and ethinyl estradiol (10/11), norethindrone and ethinyl estradiol (7/14), norethindrone and ethinyl estradiol and ferrous fumarate, nortrel, nylia, ovcon, philith, pirmella, taytulla, tri-legest, tri-legest fe, tri-norinyl, vyfemla, wera

  • lo/ovral fe

    with norgestrel, ferrous fumarate

  • norminest fe

    with ferrous fumarate, norethindrone

    Also known as lo-blisovi fe, norquest fe

  • ortho cyclen

    with norgestimate

    Also known as estarylla, mili, mono-linyah, ortho tri-cyclen, ortho tri-cyclen lo, previfem, sprintec, tri-estarylla, tri-linyah, tri-lo-estarylla, tri-lo-linyah, tri-lo-mili, tri lo sprintec, tri-mili, tri-previfem, tri-sprintec

  • ortho evra

    with norelgestromin

    Also known as xulane

  • ovral

    with norgestrel

    Also known as afirmelle, alesse, altavera, ashlyna, aviane, ayuna, balcoltra, cerinta, cryselle, daysee, elifemme, elinest, enpresse, falmina, fayosim, iclevia, introvale, jaimiess, kurvelo, lessina, levlite, levonest, levonorgestrel and ethinyl estradiol and ethinyl estradiol, levora, lo/ovral, loseasonique, lo simpesse, low-ogestrel, lybrel, marlissa, myzilra, nordette, ogestrel, orsythia, portia, preven emergency contraceptive, quartette, quasense, seasonale, seasonique, setlakin, simpesse, sylevia, triphasil, trivora, vienva

  • yasmin

    with drospirenone

    Also known as kemeya, kyra, loryna, lo-zumandimine, melamisa, nikki, syeda, yaela, yaz, zumandimine

Approval history

  • approvedJun 25, 1943

Chemistry & pharmacology

Loading structure…

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=CC(O)=CC=C34)[C@@H]1CC[C@@]2(O)C#C
Mol. weight
296.4034 g/mol
Lipinski Ro5
Pass
Rule of 3
No
Chirality
Single Stereoisomer
Inorganic
No
Polymer
No
Delivery
Oral, Topical
Availability
Prescription Only

Oral

Yes

Parenteral

No

Topical

Yes

Sources

Also known as

  • (17 alpha)-17-hydroxy-19-norpregn-4-en-20-yn-3-one, mixture with (17 alpha)-19-norpregna-1,3,5(10)-trien-20-yne-3,17-diol
  • 17alpha-ethinyl estradiol
  • 17alpha-ethinyl estradiol
  • 17 alpha-hydroxy-19-norpregn-5(10)-en-20-yn-3- one mixt. with (17 alpha)-3-methoxy-19-norpregna- 1,3,5(10)-trien-20-yn-17-ol
  • 17-ethinyl-3,17-estradiol
  • 17-ethinyl-3,17-estradiol
  • 17-ethinyl-3,17-oestradiol
  • 17-ethinyl-3,17-oestradiol
  • 17-ethinylestradiol
  • 17-ethinylestradiol
  • 17-ethinylestradiol
  • 17α-ethynylestradiol
  • 17α-ethynylestradiol
  • 19-norpregn-4-en-20-yne-3 beta,17 alpha-diol diacetate mixt. with 3-methoxy-19-norpregna-1,3,5(10) trien-20-yn-17 alpha-ol
  • angravid
  • anovlar
  • binovum
  • bisecurin
  • bisecurin i
  • brevicon
  • brevion
  • con-fer
  • drospirenone and ethinyl estradiol combination
  • drospirenone, ethinyl estradiol drug combination
  • dt 5061
  • dt-5061
  • enovid
  • enovid
  • enovid
  • enovid
  • enovid-e
  • enovid-e
  • enovid-e
  • enovid, noretynodrel
  • estinyl
  • estinyl
  • estinyl
  • estrostep
  • ethinyl esteradiol
  • ethinylestradiol
  • ethinylestradiol
  • ethinylestradiol
  • ethinylestradiol
  • ethinylestradiol
  • ethinylestradiol
  • ethinylestradiol
  • ethinyl estradiol
  • ethinyl estradiol
  • ethinyl estradiol
  • ethinyl estradiol
  • ethinyl estradiol
  • ethinyl estradiol
  • ethinyl estradiol
  • ethinyl estradiol
  • ethinyl-estradiol
  • ethinyl-estradiol
  • ethinylestradiol betadex
  • ethinylestradiol betadex
  • ethinylestradiol betadex
  • ethinylestradiol betadex
  • ethinylestradiol betadex
  • ethinylestradiol betadex
  • ethinylestradiolum
  • ethinylestradiolum
  • ethinyloestradiol
  • ethinyloestradiol
  • ethinyloestradiol
  • ethinyloestradiol
  • ethinyloestradiol
  • ethynylestradiol
  • ethynylestradiol
  • ethynyl estradiol
  • ethynyl estradiol
  • ethynyl estradiol
  • ethynylestradiol mixture with norethindrone
  • etinestryl
  • etinestryl
  • etinilestradiol
  • etinilestradiol
  • feminone
  • feminone
  • follicoral
  • follicoral
  • ginestrene
  • ginestrene
  • infecundin
  • lodose
  • loestrin
  • loestrin
  • loestrin
  • loveston
  • lynoral
  • lynoral
  • mestranol
  • mestranol
  • mestranol
  • mestranol
  • minisiston
  • minisiston
  • modicon
  • neocon
  • netasyn
  • norelgestromin / ethinyl estradiol
  • norethindrone acetate, ethinyl estradiol, ferrous fumarate drug combination
  • norimen
  • norinyl
  • norinyl
  • norinyl 1-35
  • norminest
  • norminest
  • ortho novum 7-7-7
  • ovaras
  • ovulen
  • ovulen
  • ovulen
  • ovulen-21
  • ovulen-21
  • ovulen-28
  • ovulen-28
  • ovyrmen
  • primidos
  • sesquelan
  • sh 7.1122
  • sh b 259 ab
  • synphase
  • triella
  • tri-norinyl
  • trinovum
  • yasmin
  • yasmin
  • yasmin
  • yasmin
  • yasminelle
  • yaz
  • yaz combination
  • zoran

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT07269327Phase 1Nov 24, 2025Merck KGaA
NCT07235774Phase 1Nov 5, 2025Servier
NCT07074327Phase 1Jul 11, 2025Vertex
NCT06942936Phase 1May 28, 2025AstraZeneca, Parexel
NCT06820307Phase 1Feb 25, 2025Vertex
NCT06793943Phase 1Jan 23, 2025Takeda
NCT06799884Phase 1Jan 18, 2025Idorsia Pharmaceuticals Ltd.
NCT06657105Phase 1Nov 1, 2024AstraZeneca
NCT06513104Phase 1Jul 18, 2024Novo Nordisk
NCT06380205Phase 1May 7, 2024Incyte
NCT06396221N/AMay 1, 2024Chulalongkorn University
NCT06396208N/AMay 1, 2024Chulalongkorn University
NCT06354257Phase 1Apr 5, 2024GlaxoSmithKline
NCT06310616Phase 1Mar 6, 2024ViiV Healthcare
NCT06233058Phase 1Mar 5, 2024Bio-innova Co., Ltd
NCT06233071Phase 1Feb 13, 2024Bio-innova Co., Ltd
NCT06188026Phase 1Dec 18, 2023Novo Nordisk
NCT05896384Phase 1Dec 7, 2023Boehringer Ingelheim
NCT06071442Phase 1Oct 9, 2023Alexion
NCT06076486Phase 3Sep 14, 2023Jiangsu Chia-tai Tianqing Pharmaceutical Co.,Ltd, Peking University
Showing 20 of 449 trials
Page 1 / 23

Organizations

Research & Development (258)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
BayerFor profit655952002
Johnson and JohnsonFor profit242252002
MerckFor profit221742000
PfizerFor profit181832002
Bristol-Myers SquibbFor profit161412006
National Institutes of Health (NIH)Government14441999
Boehringer IngelheimFor profit101011998
Duramed ResearchFor profit9822003
TevaFor profit9932006
AstraZenecaFor profit8812005
GlaxoSmithKlineFor profit8612007
Harvard UniversityAcademic/Hospital8642004
WyethFor profit8032002
Agile TherapeuticsFor profit7732007
Eli LillyFor profit7621989
Nobel PharmaceuticalsFor profit7712004
Novo NordiskFor profit6612006
Oregon Health and Science UniversityAcademic/Hospital6622006
University of Southern CaliforniaAcademic/Hospital6642007
Cairo UniversityAcademic/Hospital5332014
258 organizations
Page 1 / 13

Marketing (99)

OrganizationOrg typeRelationshipDate
ANDA RepositoryFor profitMKTGJul 18, 2017
Accord ResearchFor profitMKTGNov 22, 2016
Agile TherapeuticsFor profitNDA2Feb 14, 2020
AllerganFor profitMKTGDec 26, 1974
AllerganFor profitNDA2Apr 30, 1973
AllerganFor profitSYNDec 26, 1974
Allergan PLC (2015)For profitMKTGOct 11, 2016
Allied Pharmaceutical ServicesFor profitMKTGJul 18, 2017
American Home ProductsFor profitNDA2Apr 16, 1968
Amneal PharmaceuticalsFor profitMKTGSep 1, 2009
Amneal PharmaceuticalsFor profitSYNMay 12, 2021
Amneal PharmaceuticalsFor profitSYNDec 11, 2019
Amneal PharmaceuticalsFor profitSYNDec 11, 2019
Apax PartnersFor profitMKTGNov 12, 2010
ApotexFor profitMKTGSep 21, 2016
ApotexFor profitSYNSep 21, 2016
Aspen PharmaceuticalsFor profitMKTGDec 20, 2000
Aspen PharmaceuticalsFor profitNDA2Dec 20, 2000
Aurobindo PharmaFor profitMKTGJul 6, 2016
Aurobindo PharmaFor profitSYNSep 23, 2016
Avion PharmaceuticalsFor profitMKTGJan 9, 2018
Avion PharmaceuticalsFor profitNDA2Jan 9, 2018
Barr LaboratoriesFor profitMKTGFeb 28, 1992
Barr LaboratoriesFor profitSYNJun 29, 2009
BayerFor profitMKTGJul 13, 1998
BayerFor profitNDA2Jul 13, 1998
Cadence PharmaceuticalsFor profitMKTGMar 17, 1975
Cadence PharmaceuticalsFor profitNDA2Mar 17, 1975
Dr. Reddy's LaboratoriesFor profitMKTGDec 9, 2021
Dr. Reddy's LaboratoriesFor profitNDA2Apr 11, 1984
Duramed ResearchFor profitMKTGAug 12, 1999
Endo PharmaceuticalsFor profitMKTGJan 9, 2004
ExeltisFor profitMKTGJul 16, 2018
ExeltisFor profitNDA2Mar 30, 2020
ExeltisFor profitSYNAug 3, 2010
G D SearleFor profitMKTGApr 24, 1970
G D SearleFor profitNDA2Apr 24, 1970
GalenFor profitNDA2Jul 22, 2024
GlaxoSmithKlineFor profitNDA2Nov 14, 2003
Glenmark PharmaceuticalsFor profitMKTGMar 22, 2011
Glenmark PharmaceuticalsFor profitSYNFeb 23, 2016
Glenmark PharmaceuticalsFor profitSYNJun 12, 2015
Glenmark PharmaceuticalsFor profitSYNFeb 23, 2016
Healthcare Discoveries Inc.For profitMKTGJul 18, 2017
Hetero Labs LtdFor profitMKTGMar 22, 2019
Hetero Labs LtdFor profitSYNMar 22, 2019
Johnson and JohnsonFor profitSYNOct 15, 1974
Johnson and JohnsonFor profitMKTGMay 14, 1976
Johnson and JohnsonFor profitNDA2Jan 11, 1982
Jubilant Innovation Ltd.For profitMKTGDec 22, 2017
Leon PharmaFor profitMKTGAug 3, 2010
LupinFor profitMKTGDec 14, 1987
LupinFor profitSYNMay 24, 2016
LupinFor profitSYNOct 26, 2011
LupinFor profitSYNJun 25, 2012
LupinFor profitSYNMay 24, 2016
Mayne PharmaFor profitMKTGApr 11, 1984
Mayne PharmaFor profitSYNApr 28, 2017
Mayne PharmaFor profitNDA2Aug 10, 2018
MylanFor profitSYNJan 27, 2016
MylanFor profitMKTGDec 21, 2012
MylanFor profitSYNApr 16, 2014
Naari Pte LtdFor profitMKTGApr 7, 2015
Novast LabsFor profitMKTGJul 12, 2013
Novast LabsFor profitSYNDec 29, 2010
Oc PharmaFor profitMKTGApr 7, 2015
OrganonFor profitNDA2Apr 13, 1944
OrganonFor profitMKTGOct 3, 2001
OrganonFor profitSYNOct 3, 2001
Parke-DavisFor profitNDA2—
PfizerFor profitNDA2Jul 18, 1986
Pharmaceutics International, Inc.For profitMKTGJul 18, 2017
Pharmacia & UpjohnFor profitNDA2—
ScheringFor profitNDA2Jun 25, 1943
Schering-PloughFor profitNDA2Jun 25, 1943
Schering-PloughFor profitNDAJun 1, 1943
Slayback Pharma LlcFor profitMKTGDec 18, 2020
SmithKline BeechamFor profitNDA2Oct 9, 1996
Sun PharmaceuticalsFor profitMKTGJan 7, 2019
Sun PharmaceuticalsFor profitSYNJan 7, 2019
TevaFor profitSYNMay 10, 1982
TevaFor profitSYNApr 7, 2020
TevaFor profitMKTGJan 29, 1987
TevaFor profitSYNAug 25, 2021
TevaFor profitNDA2Apr 30, 1973
TherapeuticsMDFor profitMKTGAug 10, 2018
VintageFor profitMKTGNov 6, 2012
VintageFor profitSYNJan 9, 2004
Warner ChilcottFor profitMKTGJul 5, 1978
Warner ChilcottFor profitSYNAug 28, 1975
Warner ChilcottFor profitNDA2Aug 28, 1975
Watson PharmaceuticalsFor profitMKTGJan 29, 1987
Watson PharmaceuticalsFor profitSYNOct 11, 2016
Watson PharmaceuticalsFor profitSYNJan 29, 1987
Wilshire PharmaceuticalsFor profitMKTGDec 18, 2020
WyethFor profitMKTGApr 16, 1968
WyethFor profitSYNNov 1, 1984
Zydus Discovery DMCCFor profitMKTGSep 14, 2023
Zydus Discovery DMCCFor profitSYNSep 14, 2023