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Lynoral, Evra(ethinyl estradiol)
Annovera, Balcoltra, Beyaz, Cyclessa, Demulen, Estinyl, Evra, Fe, Lo Fe, Lynoral, Norlestrin, Nuvaring, Ogestrel, Ortho, Ortho Evra, Ortho Tri-cyclen, Ortho Tri-cyclen Lo, Ovral, Quartette, Rhuzdah, Safyral, Seasonale, Seasonique, Taytulla, Tri-norinyl, Twirla, Tyblume, Veraring, Yasmin, Yaz, Zovia (ethinyl estradiol) is a small molecule pharmaceutical. Ethinyl estradiol was first approved as Lynoral on 1982-01-01. It is used to treat breast neoplasms, hot flashes, hypogonadism, menorrhagia, and premature menopause amongst others in the USA. It has been approved in Europe to treat contraception. The pharmaceutical is active against estrogen receptor. In addition, it is known to target estrogen receptor beta and nuclear receptor subfamily 1 group I member 2.
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Searched
Commercial
Therapeutic Areas
Therapeutic Area
MeSH
neoplasmsD009369
urogenital diseasesD000091642
skin and connective tissue diseasesD017437
endocrine system diseasesD004700
signs and symptoms pathological conditionsD013568
therapeuticsD013812
reproductive and urinary physiological phenomenaD012101
Trade Name
FDA
EMA
Combinations
Annovera, Balcoltra, Beyaz, Cyclessa, Lo loestrin fe, Loseasonique, Nuvaring, Quartette, Rhuzdah, Safyral, Seasonale, Seasonique, Taytulla, Tri-norinyl, Twirla, Tyblume, Veraring, Yasmin, Yaz (generic drugs available since 1987-01-29, discontinued: Alesse, Aviane, Balziva, Brevicon, Cerinta, Cyclafem, Demulen, Desogen, Elifemme, Emoquette, Enpresse, Estrostep, Estrostep fe, Fayosim, Femcon fe, Femhrt, Gencept, Gildess, Kemeya, Kyra, Lessina, Levlite, Levora, Lo minastrin fe, Lo/ovral, Loestrin, Loestrin 21, Low-ogestrel, Lybrel, Microgestin, Minastrin, Mircette, Modicon, N.e.e., Norcept, Nordette, Norethin, Norinyl 1+35, Norlestrin, Norlestrin 21, Norquest fe, Nortrel, Ogestrel, Orsythia, Ortho cyclen, Ortho evra, Ortho tri-cyclen, Ortho tri-cyclen lo, Ortho-cept, Ortho-novum, Ovcon, Ovral, Pirmella, Portia, Preven emergency contraceptive, Sylevia, Tri-previfem, Triphasil, Trivora, Zovia)
Drug Products
FDA
EMA
New Drug Application (NDA)
New Drug Application (NDA)
Abbreviated New Drug Application (ANDA)
Abbreviated New Drug Application (ANDA)
Desogestrel
+
Ethinyl estradiol
Tradename
Company
Number
Date
Products
CYCLESSAAspen GlobalN-021090 RX2000-12-20
1 products, RLD, RS
Show 3 discontinued
Drospirenone
+
Ethinyl estradiol
Tradename
Company
Number
Date
Products
YASMINBayerN-021098 RX2001-05-11
1 products, RLD, RS
YAZBayerN-021676 RX2006-03-16
1 products, RLD, RS
Drospirenone
+
Ethinyl estradiol
+
Levomefolate calcium
Tradename
Company
Number
Date
Products
BEYAZBayerN-022532 RX2010-09-24
1 products, RLD, RS
SAFYRALBayerN-022574 RX2010-12-16
1 products, RLD, RS
Ethinyl estradiol
Tradename
Company
Number
Date
Products
LYNORALOrganonN-005490 DISCN1982-01-01
2 products
FEMINONEPharmacia & UpjohnN-016649 DISCN1982-01-01
1 products
ESTINYLMerck Sharp & DohmeN-005292 DISCN1982-01-01
3 products
Hide discontinued
Ethinyl estradiol
+
Ethynodiol diacetate
Tradename
Company
Number
Date
Products
DEMULEN 1/50-21G.D. SearleN-016927 DISCN1982-01-01
1 products
DEMULEN 1/50-28G.D. SearleN-016936 DISCN1982-01-01
1 products
DEMULEN 1/35-28G.D. SearleN-018160 DISCN1982-01-01
1 products
DEMULEN 1/35-21G.D. SearleN-018168 DISCN1982-01-01
1 products
Hide discontinued
Ethinyl estradiol
+
Etonogestrel
Tradename
Company
Number
Date
Products
NUVARINGOrganonN-021187 RX2001-10-03
1 products, RLD, RS
Ethinyl estradiol
+
Ferrous fumarate
+
Norethindrone
Tradename
Company
Number
Date
Products
NORQUEST FEMylanN-018926 DISCN1986-07-18
1 products
Hide discontinued
Ethinyl estradiol
+
Ferrous fumarate
+
Norethindrone acetate
Tradename
Company
Number
Date
Products
NORLESTRIN FE 1/50PfizerN-016766 DISCN1982-01-01
1 products
NORLESTRIN FE 2.5/50PfizerN-016854 DISCN1982-01-01
1 products
Hide discontinued
Ethinyl estradiol
+
Levonorgestrel
Tradename
Company
Number
Date
Products
TWIRLAAgile TherapeuticsN-204017 RX2020-02-14
1 products, RLD, RS
BALCOLTRAAvion PharmaceuticalsN-208612 RX2018-01-09
1 products, RLD, RS
TYBLUMEExeltisN-209405 RX2020-03-30
1 products, RLD, RS
SEASONALETevaN-021544 RX2003-09-05
1 products, RLD, RS
SEASONIQUETevaN-021840 RX2006-05-25
1 products, RLD, RS
LOSEASONIQUETevaN-022262 RX2008-10-24
1 products
QUARTETTETevaN-204061 RX2013-03-28
1 products, RLD, RS
Show 8 discontinued
Ethinyl estradiol
+
Norelgestromin
Tradename
Company
Number
Date
Products
ORTHO EVRAJohnson & JohnsonN-021180 DISCN2001-11-20
1 products, RLD
Hide discontinued
Ethinyl estradiol
+
Norethindrone
Tradename
Company
Number
Date
Products
NORETHINDRONE AND ETHINYL ESTRADIOL AND FERROUS FUMARATEAllerganN-022573 RX2010-12-22
1 products, RLD, RS
TRI-NORINYL 28-DAYDr Reddys LaboratoriesN-018977 RX1984-04-13
1 products, RLD, RS
Show 20 discontinued
Ethinyl estradiol
+
Norethindrone acetate
Tradename
Company
Number
Date
Products
LO LOESTRIN FEAllerganN-022501 RX2010-10-21
1 products, RLD, RS
TAYTULLAAllerganN-204426 RX2013-04-19
1 products, RLD, RS
Show 13 discontinued
Ethinyl estradiol
+
Norgestimate
Tradename
Company
Number
Date
Products
ORTHO CYCLEN-21Johnson & JohnsonN-019653 DISCN1989-12-29
1 products
ORTHO CYCLEN-28Johnson & JohnsonN-019653 DISCN1989-12-29
1 products, RLD
ORTHO TRI-CYCLENJohnson & JohnsonN-019697 DISCN1992-07-03
2 products
ORTHO TRI-CYCLEN LOJohnson & JohnsonN-021241 DISCN2002-08-22
1 products, RLD
Hide discontinued
Ethinyl estradiol
+
Norgestrel
Tradename
Company
Number
Date
Products
LO/OVRALCadence PharmaceuticalsN-017612 DISCN1982-01-01
1 products, RLD
OVRALWYETH PHARMSN-016672 DISCN1982-01-01
1 products
OVRAL-28WYETH PHARMSN-016806 DISCN1982-01-01
1 products
LO/OVRAL-28WYETH PHARMSN-017802 DISCN1982-01-01
1 products, RLD
Hide discontinued
Ethinyl estradiol
+
Segesterone acetate
Tradename
Company
Number
Date
Products
ANNOVERAMayne GroupN-209627 RX2018-08-10
1 products, RLD, RS
Labels
FDA
EMA
Brand Name
Status
Last Update
afirmelleANDA2021-09-03
altaveraANDA2023-03-02
alyacen 7/7/7ANDA2023-06-07
annoveraNew Drug Application2021-01-13
aranelleANDA2017-08-31
ashlynaANDA2021-05-31
aurovela 24 feANDA2023-06-14
avianeANDA2022-11-15
ayunaANDA2021-06-04
balcoltraNew Drug Application2019-12-10
Show 97 more
Indications
FDA
EMA
Indication
Ontology
MeSH
ICD-10
breast neoplasmsEFO_0003869D001943C50
hot flashes—D019584—
hypogonadismHP_0000815D007006E23.0
menorrhagiaHP_0000132D008595N92.0
premature menopauseHP_0008209D008594E28.31
primary ovarian insufficiencyEFO_0004266D016649E28.3
prostatic neoplasms—D011471C61
Agency Specific
FDA
EMA
Expiration
Code
ETHINYL ESTRADIOL / SEGESTERONE ACETATE, ANNOVERA, MAYNE PHARMA
2023-08-10NCE
ETHINYL ESTRADIOL / LEVONORGESTREL, TYBLUME, EXELTIS USA INC
2023-03-30NDF
ETHINYL ESTRADIOL / LEVONORGESTREL, TWIRLA, AGILE
2023-02-14NP
Patent Expiration
Patent
Expires
Flag
FDA Information
Ethinyl Estradiol / Segesterone Acetate, Annovera, Mayne Pharma
109186492039-06-21DP
109258822039-06-21DP
109401572039-06-21DP
115293082039-06-21DP
106320662039-02-01U-2786, U-2787
107656282039-02-01U-2786, U-2787
107800472039-02-01U-2786, U-2787
Drospirenone / Ethinyl Estradiol / Levomefolate Calcium, Beyaz, Bayer Hlthcare
116177512030-07-17DPU-1, U-3572, U-3573, U-3574
86175972030-02-08DP
Ethinyl Estradiol / Levonorgestrel, Quartette, Teva Branded Pharm
84153322029-03-11DP
84502992025-10-07U-1
Ethinyl Estradiol / Norethindrone Acetate, Lo Loestrin Fe, Apil
77049842029-02-02U-1, U-1090
Ethinyl Estradiol / Levonorgestrel, Loseasonique, Teva Branded Pharm
78551902028-12-05U-1
78586052023-06-23DP
76155452023-06-15U-1
Ethinyl Estradiol / Levonorgestrel, Twirla, Agile
82469782028-08-26DP
87478882028-07-10DP
90503482028-07-10DP
Ethinyl Estradiol / Levonorgestrel, Balcoltra, Avion Pharms
78380422027-06-01DPU-3251
Ethinyl Estradiol / Levonorgestrel, Seasonique, Teva Branded Pharm
73209692024-01-30U-828
ATC Codes
G: Genito urinary system and sex hormones
— G03: Sex hormones and modulators of the genital system
— G03A: Hormonal contraceptives for systemic use
— G03AA: Progestogens and estrogen systemic contraceptives, fixed combinations
— G03AA01: Etynodiol and ethinylestradiol
— G03AA02: Quingestanol and ethinylestradiol
— G03AA03: Lynestrenol and ethinylestradiol
— G03AA04: Megestrol and ethinylestradiol
— G03AA05: Norethisterone and ethinylestradiol
— G03AA06: Norgestrel and ethinylestradiol
— G03AA07: Levonorgestrel and ethinylestradiol
— G03AA08: Medroxyprogesterone and ethinylestradiol
— G03AA09: Desogestrel and ethinylestradiol
— G03AA10: Gestodene and ethinylestradiol
— G03AA11: Norgestimate and ethinylestradiol
— G03AA12: Drospirenone and ethinylestradiol
— G03AA13: Norelgestromin and ethinylestradiol
— G03AA15: Chlormadinone and ethinylestradiol
— G03AA16: Dienogest and ethinylestradiol
— G03AB: Progestogens and estrogens systemic contraceptives, sequential preparations
— G03AB01: Megestrol and ethinylestradiol
— G03AB02: Lynestrenol and ethinylestradiol
— G03AB03: Levonorgestrel and ethinylestradiol
— G03AB04: Norethisterone and ethinylestradiol
— G03AB05: Desogestrel and ethinylestradiol
— G03AB06: Gestodene and ethinylestradiol
— G03AB07: Chlormadinone and ethinylestradiol
— G03AB09: Norgestimate and ethinylestradiol
— G03C: Estrogens, sex hormones and modulators of the genital system
— G03CA: Natural and semisynthetic estrogens, plain
— G03CA01: Ethinylestradiol
L: Antineoplastic and immunomodulating agents
— L02: Endocrine therapy antineoplastic and immunomodulating agents
— L02A: Hormones and related agents
— L02AA: Estrogens, endocrine therapy drugs
— L02AA03: Ethinylestradiol
HCPCS
Code
Description
J7294
Segesterone acetate and ethinyl estradiol 0.15mg, 0.013mg per 24 hours; yearly vaginal system, each
J7295
Ethinyl estradiol and etonogestrel 0.015mg, 0.12mg per 24 hours; monthly vaginal ring, each
Clinical
Clinical Trials
828 clinical trials
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Indications Phases 4
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
Healthy volunteers/patients—1821352193
ContraceptionD003267111031171281
Polycystic ovary syndromeD011085EFO_0000660E28.21238721
TuberculosisD014376EFO_0000774A15-A1951251—19
InfectionsD007239EFO_00005447131113
CataractD002386EFO_0001059H26.91—19213
Hiv infectionsD015658EFO_0000764B2062—1211
EndophthalmitisD0098772534—11
PneumoniaD011014EFO_0003106J18—252110
Bacterial infectionsD001424A493—1419
Show 56 more
Indications Phases 3
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
Pulmonary tuberculosisD014397EFO_1000049A15—118—217
Multidrug-resistant tuberculosisD018088EFO_0007381—78——9
Premenstrual syndromeD011293N94.3—14—27
HypertensionD006973EFO_0000537I10221——5
Breast neoplasmsD001943EFO_0003869C50113——5
Community-acquired infectionsD017714—23——5
Lung diseasesD008171EFO_0003818J98.4212——4
Rheumatoid arthritisD001172EFO_0000685M06.93—1——4
Extensively drug-resistant tuberculosisD054908—44——4
Systemic lupus erythematosusD008180EFO_0002690M322—1—14
Show 45 more
Indications Phases 2
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
PharmacokineticsD010599121——215
NeoplasmsD009369C8041——16
Parkinson diseaseD010300EFO_0002508G2031———4
MetrorrhagiaD008796HP_0100608N92.1—3———3
DepressionD003863F33.9—1——12
MenorrhagiaD008595N92.011——12
CholangitisD002761K83.0—1———1
Anorexia nervosaD000856EFO_0004215F50.0—1———1
PregnancyD011247EFO_0002950Z33.1—1———1
HemostasisD006487—1———1
Show 14 more
Indications Phases 1
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
Type 2 diabetes mellitusD003924EFO_0001360E1110————10
Therapeutic equivalencyD0138109———110
Hepatitis cD006526B19.25————5
Heart failureD006333EFO_0003144I502———35
SchizophreniaD012559EFO_0000692F204————4
Drug interactionsD0043474————4
Alzheimer diseaseD000544EFO_0000249F034————4
AdenomyosisD062788EFO_1001757N80.01———23
Cystic fibrosisD003550EFO_0000390E843————3
AsthmaD001249EFO_0000270J453————3
Show 52 more
Indications Without Phase
Indication
MeSH
Ontology
ICD-10
Ph 1
Ph 2
Ph 3
Ph 4
Other
Total
Long qt syndromeD008133HP_0001657I45.81————22
Venous thrombosisD020246HP_0004936I82.40————22
Pathologic dilatationD004108————22
KeratoconusD007640EFO_0004223H18.6————22
RegenerationD012038————22
PeritonitisD010538EFO_0008588K65————22
DeliriumD003693R41.0————11
Mycoplasma pneumoniaD011019EFO_0007387J15.7————11
AppendicitisD001064EFO_0007149K37————11
Chemical and drug induced liver injuryD056486————11
Show 23 more
Epidemiology
Epidemiological information for investigational and approved indications
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Drug
General
Drug common nameETHINYL ESTRADIOL
INNethinylestradiol
Description
17alpha-ethynylestradiol is a 3-hydroxy steroid that is estradiol substituted by a ethynyl group at position 17. It is a xenoestrogen synthesized from estradiol and has been shown to exhibit high estrogenic potency on oral administration. It has a role as a xenoestrogen. It is a 17-hydroxy steroid, a terminal acetylenic compound and a 3-hydroxy steroid. It is functionally related to a 17beta-estradiol and an estradiol.
Classification
Small molecule
Drug classestrogens
Image (chem structure or protein)
Structure (InChI/SMILES or Protein Sequence)
C#C[C@]1(O)CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@@]21C
Identifiers
PDB4X1F
CAS-ID57-63-6
RxCUI4124
ChEMBL IDCHEMBL691
ChEBI ID4903
PubChem CID5991
DrugBankDB00977
UNII ID423D2T571U (ChemIDplus, GSRS)
Target
Agency Approved
ESR1
ESR1
Organism
Homo sapiens
Gene name
ESR1
Gene synonyms
ESR, NR3A1
NCBI Gene ID
2099
Protein name
estrogen receptor
Protein synonyms
E2 receptor alpha, ER-alpha, Estradiol receptor, estrogen nuclear receptor alpha, estrogen receptor alpha E1-E2-1-2, estrogen receptor alpha E1-N2-E2-1-2, Nuclear receptor subfamily 3 group A member 1, oestrogen receptor alpha
Uniprot ID
Q9UIS7
Mouse ortholog
Esr1 (13982)
estrogen receptor (Q9QY52)
Alternate
ESR2
ESR2
NR1I2
NR1I2
Organism
Homo sapiens
Gene name
ESR2
Gene synonyms
ESTRB, NR3A2
NCBI Gene ID
2100
Protein name
estrogen receptor beta
Protein synonyms
estrogen receptor beta 2, estrogen receptor beta 4, Nuclear receptor subfamily 3 group A member 2, oestrogen receptor beta
Uniprot ID
Q92731
Mouse ortholog
Esr2 (13983)
estrogen receptor beta (O08537)
Variants
Clinical Variant
No data
Financial
Nuvaring - Organon
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Nuvaring - Merck Sharp & Dohme
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Loestrin - Allergan
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Loestrin - Warner Chilcott
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Loestrin - AbbVie
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Annovera - TherapeuticsMD
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Tabular view
Trends
PubMed Central
Top Terms for Disease or Syndrome:
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Safety
Black-box Warning
Black-box warning for: Altavera, Annovera, Ashlyna, Aurovela 24 fe, Ayuna, Balcoltra, Beyaz, Blisovi fe 1/20 , Cryselle, Cyclafem 1/35, Cyonanz, Dasetta 1/35, Daysee , Drospirenone/ethinyl estradiol/levomefolate calcium and levomefolate calcium, Eluryng, Emoquette, Enskyce , Estarylla, Fayosim , Femhrt, Finzala, Fyavolv, Gemmily, Hailey 1.5/30, Haloette, Iclevia, Introvale, Isibloom, Jaimiess, Junel fe, Kaitlib fe , Kalliga, Kurvelo , Levora, Lo loestrin fe, Lo simpesse, Lo-zumandimine, Loryna, Loseasonique, Low-ogestrel, Marlissa, Merzee, Mibelas 24 fe , Microgestin 1.5/30 , Minastrin 24 fe, Mono-linyah , Myzilra, Nexesta fe, Nikki , Nuvaring, Nylia 1/35, Ortho cyclen ortho tri cyclen, Previfem, Quartette, Seasonique, Setlakin , Syeda, Taytulla, Tri-estarylla, Tri-legest fe, Tri-linyah , Tri-lo-mili, Tri-mili, Tri-sprintec, Twirla, Tyblume, Tydemy , Volnea, Wera , Xulane, Yasmin, Yaz, Zumandimine
Adverse Events
Top Adverse Reactions
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85,982 adverse events reported
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