U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C20H28O2
Molecular Weight 300.4351
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHYNODIOL

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]3([H])[C@@]4([H])CC[C@H](O)C=C4CC[C@@]23[H]

InChI

InChIKey=JYILPERKVHXLNF-QMNUTNMBSA-N
InChI=1S/C20H28O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,14-18,21-22H,4-11H2,2H3/t14-,15-,16+,17+,18-,19-,20-/m0/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including http://nwpeu.de/media/wysiwyg/PDFs/Femulen_PIL_.pdf

Etynodiol (used in a form of diacetate) is a steroid that was used as a contraceptive drug. Etynodiol diacetate and etynodiol are rapidly metabolized to an active metabolite, norethisterone, which binds to progesterone receptor and modulates its activity.

Originator

Curator's Comment: Now is a part of Pfizer.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
62000.0 nM [IC50]
0.13 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
FEMULEN

Approved Use

Femulen helps to prevent you becoming pregnant.
Doses

Doses

DosePopulationAdverse events​
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Disc. AE: Intermenstrual bleeding, Amenorrhoea...
AEs leading to
discontinuation/dose reduction:
Intermenstrual bleeding (1.4%)
Amenorrhoea (4%)
Menstruation delayed (0.5%)
Menstrual cramps (0.7%)
Oedema (0.2%)
Hypertension (0.2%)
Genital boil (0.2%)
Painful joints (0.5%)
Migraine headache (2.1%)
Dizziness (0.7%)
Nervousness (0.7%)
Irritable (0.2%)
Depression (1.9%)
Dysphoria (0.2%)
Lethargy (0.2%)
Loss of libido (1.2%)
Eye inflammation (0.5%)
Vomiting (1.2%)
Flatulence (1.4%)
Breast tenderness (1.2%)
Urinary hesitancy (0.2%)
Acne (0.5%)
Weight gain (1.6%)
Sources:
0.5 mg steady, oral
Recommended
Dose: 0.5 mg
Route: oral
Route: steady
Dose: 0.5 mg
Co-administed with::
mestranol(0.1 mg; oral; 1/day)
Sources:
healthy
n = 178
Health Status: healthy
Sex: F
Population Size: 178
Sources:
Disc. AE: Nausea, Bleeding breakthrough...
AEs leading to
discontinuation/dose reduction:
Nausea (0.6%)
Bleeding breakthrough (1.1%)
Mastopathy (2.8%)
Dysmenorrhoea (3.9%)
Neuropathy (3.9%)
Headache (1.1%)
Abnormal weight gain (0.6%)
Thrombophlebitis (0.6%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Dysphoria 0.2%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Genital boil 0.2%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Hypertension 0.2%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Irritable 0.2%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Lethargy 0.2%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Oedema 0.2%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Urinary hesitancy 0.2%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Acne 0.5%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Eye inflammation 0.5%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Menstruation delayed 0.5%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Painful joints 0.5%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Dizziness 0.7%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Menstrual cramps 0.7%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Nervousness 0.7%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Breast tenderness 1.2%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Loss of libido 1.2%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Vomiting 1.2%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Flatulence 1.4%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Intermenstrual bleeding 1.4%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Weight gain 1.6%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Depression 1.9%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Migraine headache 2.1%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Amenorrhoea 4%
Disc. AE
0.5 mg 1 times / day steady, oral
Recommended
Dose: 0.5 mg, 1 times / day
Route: oral
Route: steady
Dose: 0.5 mg, 1 times / day
Sources:
healthy, 16-47
n = 425
Health Status: healthy
Age Group: 16-47
Sex: F
Population Size: 425
Sources:
Abnormal weight gain 0.6%
Disc. AE
0.5 mg steady, oral
Recommended
Dose: 0.5 mg
Route: oral
Route: steady
Dose: 0.5 mg
Co-administed with::
mestranol(0.1 mg; oral; 1/day)
Sources:
healthy
n = 178
Health Status: healthy
Sex: F
Population Size: 178
Sources:
Nausea 0.6%
Disc. AE
0.5 mg steady, oral
Recommended
Dose: 0.5 mg
Route: oral
Route: steady
Dose: 0.5 mg
Co-administed with::
mestranol(0.1 mg; oral; 1/day)
Sources:
healthy
n = 178
Health Status: healthy
Sex: F
Population Size: 178
Sources:
Thrombophlebitis 0.6%
Disc. AE
0.5 mg steady, oral
Recommended
Dose: 0.5 mg
Route: oral
Route: steady
Dose: 0.5 mg
Co-administed with::
mestranol(0.1 mg; oral; 1/day)
Sources:
healthy
n = 178
Health Status: healthy
Sex: F
Population Size: 178
Sources:
Bleeding breakthrough 1.1%
Disc. AE
0.5 mg steady, oral
Recommended
Dose: 0.5 mg
Route: oral
Route: steady
Dose: 0.5 mg
Co-administed with::
mestranol(0.1 mg; oral; 1/day)
Sources:
healthy
n = 178
Health Status: healthy
Sex: F
Population Size: 178
Sources:
Headache 1.1%
Disc. AE
0.5 mg steady, oral
Recommended
Dose: 0.5 mg
Route: oral
Route: steady
Dose: 0.5 mg
Co-administed with::
mestranol(0.1 mg; oral; 1/day)
Sources:
healthy
n = 178
Health Status: healthy
Sex: F
Population Size: 178
Sources:
Mastopathy 2.8%
Disc. AE
0.5 mg steady, oral
Recommended
Dose: 0.5 mg
Route: oral
Route: steady
Dose: 0.5 mg
Co-administed with::
mestranol(0.1 mg; oral; 1/day)
Sources:
healthy
n = 178
Health Status: healthy
Sex: F
Population Size: 178
Sources:
Dysmenorrhoea 3.9%
Disc. AE
0.5 mg steady, oral
Recommended
Dose: 0.5 mg
Route: oral
Route: steady
Dose: 0.5 mg
Co-administed with::
mestranol(0.1 mg; oral; 1/day)
Sources:
healthy
n = 178
Health Status: healthy
Sex: F
Population Size: 178
Sources:
Neuropathy 3.9%
Disc. AE
0.5 mg steady, oral
Recommended
Dose: 0.5 mg
Route: oral
Route: steady
Dose: 0.5 mg
Co-administed with::
mestranol(0.1 mg; oral; 1/day)
Sources:
healthy
n = 178
Health Status: healthy
Sex: F
Population Size: 178
Sources:
PubMed

PubMed

TitleDatePubMed
Cardiovascular birth defects and antenatal exposure to female sex hormones.
1977 Jan 13
Patents

Patents

Sample Use Guides

Take one pill (each Femulen pill contains 500 ug of etynodiol diacetate) each day. Start on the first day of your next period.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
ETHYNODIOL
MI  
Common Name English
etynodiol [INN]
Common Name English
17.ALPHA.-ETHYNYL-4-OESTRENE-3.BETA.,17.BETA.-DIOL
Common Name English
ETYNODIOL
INN   WHO-DD  
INN  
Official Name English
ESTR-4-ENE-3,17-DIOL, 17-ETHYNYL-, (3.BETA.,17.BETA.)-
Common Name English
3.BETA.-HYDROXYLYNESTRENOL
Common Name English
(3.BETA.,17.BETA.)-17-ETHYNYLESTR-4-ENE-3,17-DIOL
Systematic Name English
Etynodiol [WHO-DD]
Common Name English
ETHYNODIOL [MI]
Common Name English
19-NORPREGN-4-EN-20-YNE-3,17-DIOL, (3.BETA.,17.ALPHA.)-
Systematic Name English
Classification Tree Code System Code
WHO-VATC QG03FA06
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
WHO-ATC G03FA06
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
NDF-RT N0000011301
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
LIVERTOX 385
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
NCI_THESAURUS C776
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
WHO-VATC QG03AA01
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
WHO-VATC QG03DC06
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
WHO-ATC G03DC06
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
WHO-ATC G03AA01
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
NDF-RT N0000175602
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
Code System Code Type Description
FDA UNII
9E01C36A9S
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
EVMPD
SUB07350MIG
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
WIKIPEDIA
Etynodiol
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
RXCUI
24591
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
214-971-5
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
MERCK INDEX
m5179
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY Merck Index
SMS_ID
100000082137
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
CAS
1231-93-2
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
HSDB
7897
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
PUBCHEM
14687
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
CHEBI
50785
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200624
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID1023025
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
INN
1336
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
DAILYMED
9E01C36A9S
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
MESH
C014546
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
DRUG BANK
DB13866
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
DRUG CENTRAL
1095
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY
NCI_THESAURUS
C72771
Created by admin on Fri Dec 15 15:04:05 GMT 2023 , Edited by admin on Fri Dec 15 15:04:05 GMT 2023
PRIMARY