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ethinylestradiol 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definition	Drug id	CAS RN
estrogens	1082	57-63-6

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: ethinylestradiol betadex ethynyl estradiol ethinylestradiol ethinyl estradiol 17-ethinylestradiol ethinyloestradiol	A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES. Molecular weight: 296.41 Formula: C20H24O2 CLOGP: 3.68 LIPINSKI: 0 HAC: 2 HDO: 2 TPSA: 40.46 ALOGS: -4.64 ROTB: 0 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

ethinylestradiol betadex
ethynyl estradiol
ethinylestradiol
ethinyl estradiol
17-ethinylestradiol
ethinyloestradiol

A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.

Molecular weight: 296.41
Formula: C20H24O2
CLOGP: 3.68
LIPINSKI: 0
HAC: 2
HDO: 2
TPSA: 40.46
ALOGS: -4.64
ROTB: 0

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

Dose	Unit	Route
25	mcg	O
1.50	mg	O

ADMET properties:

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Property	Value	Reference
t_half (Half-life)	9.70 hours	Lombardo F, Berellini G, Obach RS
CL (Clearance)	7 mL/min/kg	Lombardo F, Berellini G, Obach RS
BA (Bioavailability)	40 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution)	4.30 L/kg	Lombardo F, Berellini G, Obach RS
EoM (Fraction excreted unchanged in urine)	3 %	Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.10 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
S (Water solubility)	0.01 mg/mL	Bocci G, Oprea TI, Benet LZ
fu (Fraction unbound in plasma)	0.01 %	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
July 23, 2010	PMDA	Bayer Yakuhin
June 25, 1943	FDA	SCHERING

FDA Adverse Event Reporting System (Female)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Pulmonary embolism	862.97	17.88	434	12315	116250	63360023
Unintended pregnancy	678.65	17.88	172	12577	6007	63470266
Intermenstrual bleeding	589.51	17.88	162	12587	7764	63468509
Device expulsion	478.60	17.88	200	12549	34722	63441551
Deep vein thrombosis	443.59	17.88	250	12499	83550	63392723
Inappropriate schedule of product administration	339.65	17.88	228	12521	103737	63372536
No adverse event	319.41	17.88	159	12590	41246	63435027
Incorrect product administration duration	301.93	17.88	106	12643	11440	63464833
Pregnancy with contraceptive device	276.48	17.88	80	12669	4614	63471659
Product quality issue	208.50	17.88	114	12635	35751	63440522

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FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

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MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients not taking drug not having adverse event
Pulmonary embolism	532.23	22.63	298	8960	171356	79563774
Intermenstrual bleeding	481.03	22.63	116	9142	5768	79729362
Unintended pregnancy	477.95	22.63	107	9151	3826	79731304
Device expulsion	318.93	22.63	118	9140	25743	79709387
Deep vein thrombosis	244.54	22.63	160	9098	120759	79614371
Incorrect product administration duration	217.54	22.63	73	9185	11949	79723181
Inappropriate schedule of product administration	211.42	22.63	152	9106	133476	79601654
Pregnancy with contraceptive device	208.29	22.63	54	9204	3600	79731530
Heavy menstrual bleeding	140.43	22.63	55	9203	13956	79721174
Medical device discomfort	130.09	22.63	32	9226	1722	79733408

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	G03AA01	GENITO URINARY SYSTEM AND SEX HORMONES SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE Progestogens and estrogens, fixed combinations
ATC	G03AA02	GENITO URINARY SYSTEM AND SEX HORMONES SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE Progestogens and estrogens, fixed combinations
ATC	G03AA03	GENITO URINARY SYSTEM AND SEX HORMONES SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE Progestogens and estrogens, fixed combinations
ATC	G03AA04	GENITO URINARY SYSTEM AND SEX HORMONES SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE Progestogens and estrogens, fixed combinations
ATC	G03AA05	GENITO URINARY SYSTEM AND SEX HORMONES SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE Progestogens and estrogens, fixed combinations
ATC	G03AA06	GENITO URINARY SYSTEM AND SEX HORMONES SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE Progestogens and estrogens, fixed combinations
ATC	G03AA07	GENITO URINARY SYSTEM AND SEX HORMONES SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE Progestogens and estrogens, fixed combinations
ATC	G03AA08	GENITO URINARY SYSTEM AND SEX HORMONES SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE Progestogens and estrogens, fixed combinations
ATC	G03AA09	GENITO URINARY SYSTEM AND SEX HORMONES SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE Progestogens and estrogens, fixed combinations
ATC	G03AA10	GENITO URINARY SYSTEM AND SEX HORMONES SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE Progestogens and estrogens, fixed combinations

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Drug Use | Suggest Off label Use Form| |View source of the data|

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Disease	Relation	SNOMED_ID	DOID
Premenstrual dysphoric disorder	indication	596004
Contraception	indication	13197004
Atrophic vaginitis	indication	52441000
Acne vulgaris	indication	88616000
Postmenopausal osteoporosis	indication	102447009
Menopausal flushing	indication	198436008
Atrophic vulva	indication	248861000	DOID:14275
Dysmenorrhea	indication	266599000
Controlled ovarian stimulation	indication	732970000
Amenorrhea	off-label use	14302001	DOID:13938

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🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	11.13	acidic

Orange Book patent data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent use
0.013MG/24HR;0.15MG/24HR	ANNOVERA	MAYNE PHARMA	N209627	Aug. 10, 2018	RX	RING	VAGINAL	10632066	Feb. 1, 2039	METHOD OF CONTRACEPTION BY INSERTING A VAGINAL SYSTEM FOR UP TO 13 21/7-DAY (IN/OUT) CYCLES, WHEREIN EFFICACY REQUIRES THE SYSTEM CANNOT BE OUT OF THE VAGINA FOR MORE THAN 2 CUMULATIVE HOURS IN ANY SUCH CYCLE WITHOUT USING ALTERNATIVE CONTRACEPTION
0.013MG/24HR;0.15MG/24HR	ANNOVERA	MAYNE PHARMA	N209627	Aug. 10, 2018	RX	RING	VAGINAL	10632066	Feb. 1, 2039	METHOD OF PREVENTING PREGNANCY BY INSERTING A VAGINAL SYSTEM CONTAINING 103 MG OF SEGESTERONE ACETATE AND 17.4 MG ETHINYL ESTRADIOL INTO A VAGINA FOR UP TO THIRTEEN 21/7-DAY (IN/OUT) CYCLES
0.013MG/24HR;0.15MG/24HR	ANNOVERA	MAYNE PHARMA	N209627	Aug. 10, 2018	RX	RING	VAGINAL	10765628	Feb. 1, 2039	METHOD OF CONTRACEPTION BY INSERTING A VAGINAL SYSTEM FOR UP TO 13 21/7-DAY (IN/OUT) CYCLES, WHEREIN EFFICACY REQUIRES THE SYSTEM CANNOT BE OUT OF THE VAGINA FOR MORE THAN 2 CUMULATIVE HOURS IN ANY SUCH CYCLE WITHOUT USING ALTERNATIVE CONTRACEPTION
0.013MG/24HR;0.15MG/24HR	ANNOVERA	MAYNE PHARMA	N209627	Aug. 10, 2018	RX	RING	VAGINAL	10765628	Feb. 1, 2039	METHOD OF PREVENTING PREGNANCY BY INSERTING A VAGINAL SYSTEM CONTAINING 103 MG OF SEGESTERONE ACETATE AND 17.4 MG ETHINYL ESTRADIOL INTO A VAGINA FOR UP TO THIRTEEN 21/7-DAY (IN/OUT) CYCLES
0.013MG/24HR;0.15MG/24HR	ANNOVERA	MAYNE PHARMA	N209627	Aug. 10, 2018	RX	RING	VAGINAL	10780047	Feb. 1, 2039	METHOD OF CONTRACEPTION BY INSERTING A VAGINAL SYSTEM FOR UP TO 13 21/7-DAY (IN/OUT) CYCLES, WHEREIN EFFICACY REQUIRES THE SYSTEM CANNOT BE OUT OF THE VAGINA FOR MORE THAN 2 CUMULATIVE HOURS IN ANY SUCH CYCLE WITHOUT USING ALTERNATIVE CONTRACEPTION
0.013MG/24HR;0.15MG/24HR	ANNOVERA	MAYNE PHARMA	N209627	Aug. 10, 2018	RX	RING	VAGINAL	10780047	Feb. 1, 2039	METHOD OF PREVENTING PREGNANCY BY INSERTING A VAGINAL SYSTEM CONTAINING 103 MG OF SEGESTERONE ACETATE AND 17.4 MG ETHINYL ESTRADIOL INTO A VAGINA FOR UP TO THIRTEEN 21/7-DAY (IN/OUT) CYCLES
0.01MG,0.01MG,N/A;1MG,N/A,N/A	LO MINASTRIN FE	APIL	N204654	July 24, 2013	DISCN	TABLET, CHEWABLE, TABLET	ORAL	7704984	Feb. 2, 2029	PREVENTION OF PREGNANCY
0.01MG,0.01MG;1MG,N/A	LO LOESTRIN FE	APIL	N022501	Oct. 21, 2010	RX	TABLET	ORAL	7704984	Feb. 2, 2029	LO LOESTRIN FE IS INDICATED FOR THE PREVENTION OF PREGNANCY IN WOMEN WHO ELECT TO USE ORAL CONTRACEPTIVES AS A METHOD OF CONTRACEPTION
0.02MG,0.15MG;0.025MG,0.15MG;0.03MG,0.15MG;0.01MG,N/A	QUARTETTE	TEVA BRANDED PHARM	N204061	March 28, 2013	RX	TABLET	ORAL	8450299	Oct. 7, 2025	PREVENTION OF PREGNANCY
0.02MG,0.1MG;0.01MG,N/A	LOSEASONIQUE	TEVA BRANDED PHARM	N022262	Oct. 24, 2008	RX	TABLET	ORAL	7615545	June 15, 2023	PREVENTION OF PREGNANCY

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Orange Book exclusivity data (new drug applications)

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Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Exclusivity date	Description
0.013MG/24HR;0.15MG/24HR	ANNOVERA	MAYNE PHARMA	N209627	Aug. 10, 2018	RX	RING	VAGINAL	Aug. 10, 2023	NEW CHEMICAL ENTITY
0.02MG;0.1MG	TYBLUME	EXELTIS USA INC	N209405	March 30, 2020	RX	TABLET	ORAL	March 30, 2023	NEW DOSAGE FORM
0.03MG/24HR;0.12MG/24HR	TWIRLA	AGILE	N204017	Feb. 14, 2020	RX	SYSTEM	TRANSDERMAL	Feb. 14, 2023	NEW PRODUCT

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Bioactivity Summary:

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Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Estrogen receptor	Nuclear hormone receptor	P03372	ESR1_HUMAN	AGONIST	Kd	9.83	WOMBAT-PK	CHEMBL
Nuclear receptor subfamily 1 group I member 3	Nuclear hormone receptor	Q14994	NR1I3_HUMAN		IC50	5.52	CHEMBL
Mu-type opioid receptor	GPCR	P35372	OPRM_HUMAN		Ki	4.96	DRUG MATRIX
Adenosine receptor A2a	GPCR	P29274	AA2AR_HUMAN		Ki	4.93	DRUG MATRIX
Sodium-dependent serotonin transporter	Transporter	P31645	SC6A4_HUMAN		Ki	7.54	DRUG MATRIX
Sodium-dependent noradrenaline transporter	Transporter	P23975	SC6A2_HUMAN		Ki	6.02	DRUG MATRIX
Aldehyde oxidase	Enzyme	Q06278	AOXA_HUMAN		IC50	6.24	WOMBAT-PK
Glucocorticoid receptor	Nuclear hormone receptor	P04150	GCR_HUMAN		Ki	6.11	DRUG MATRIX
Sodium-dependent dopamine transporter	Transporter	Q01959	SC6A3_HUMAN		Ki	6.35	DRUG MATRIX
Adenosine receptor A3	GPCR	P0DMS8	AA3R_HUMAN		Ki	4.73	DRUG MATRIX

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External reference:

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ID	Source
3WF	PDB_CHEM_ID
001286	NDDF
126097006	SNOMEDCT_US
15432003	SNOMEDCT_US
4018022	VUID
4018022	VANDF
4124	RXNORM
423D2T571U	UNII
437	INN_ID
4698	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Amethyst	HUMAN PRESCRIPTION DRUG LABEL	2	0480-3472	TABLET	20 ug	ORAL	ANDA	24 sections
Amethyst	HUMAN PRESCRIPTION DRUG LABEL	2	0480-3472	TABLET	20 ug	ORAL	ANDA	24 sections
ANNOVERA	HUMAN PRESCRIPTION DRUG LABEL	2	50261-313	RING	17.40 mg	VAGINAL	NDA	32 sections
ANNOVERA	HUMAN PRESCRIPTION DRUG LABEL	2	50261-313	RING	17.40 mg	VAGINAL	NDA	32 sections
Etonogestrel and Ethinyl Estradiol	HUMAN PRESCRIPTION DRUG LABEL	2	0093-7679	INSERT, EXTENDED RELEASE	0.02 mg	VAGINAL	ANDA	29 sections
Etonogestrel and Ethinyl Estradiol	HUMAN PRESCRIPTION DRUG LABEL	2	0093-7679	INSERT, EXTENDED RELEASE	0.02 mg	VAGINAL	ANDA	29 sections
Etonogestrel/Ethinyl Estradiol	HUMAN PRESCRIPTION DRUG LABEL	2	50090-5959	INSERT, EXTENDED RELEASE	0.02 mg	VAGINAL	NDA AUTHORIZED GENERIC	29 sections
femhrt	HUMAN PRESCRIPTION DRUG LABEL	2	0430-0145	TABLET	2.50 ug	ORAL	NDA	33 sections
Jinteli	HUMAN PRESCRIPTION DRUG LABEL	2	0093-3122	TABLET	5 ug	ORAL	ANDA	29 sections
Junel21 Day	HUMAN PRESCRIPTION DRUG LABEL	2	0555-9025	TABLET	20 ug	ORAL	ANDA	15 sections

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