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

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H32O4
Molecular Weight 384.5085
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHYNODIOL DIACETATE

SMILES

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

InChI

InChIKey=ONKUMRGIYFNPJW-KIEAKMPYSA-N
InChI=1S/C24H32O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,14,18-22H,6-13H2,2-4H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1

HIDE SMILES / InChI

Molecular Formula C24H32O4
Molecular Weight 384.5085
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:02:22 GMT 2023
Edited
by admin
on Fri Dec 15 15:02:22 GMT 2023
Record UNII
62H10A1236
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHYNODIOL DIACETATE
JAN   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
ETHYNODIOL DIACETATE [USP-RS]
Common Name English
ETHYNODIOL DIACETATE [JAN]
Common Name English
ETHYNODIOL DIACETATE COMPONENT OF OVULEN
Common Name English
ETHYNODIOL DIACETATE [MI]
Common Name English
OVULEN COMPONENT ETHYNODIOL DIACETATE
Common Name English
ETHYNODIOL DIACETATE [USP MONOGRAPH]
Common Name English
ETHYNODIOL DIACETATE [ORANGE BOOK]
Common Name English
ETHYNODIOL DIACETATE COMPONENT OF KELNOR
Common Name English
19-NORPREGN-4-EN-20-YNE-3,17-DIOL, DIACETATE, (3.BETA.,17.ALPHA.)-
Common Name English
ZOVIA COMPONENT ETHYNODIOL DIACETATE
Brand Name English
ETYNODIOL ACETATE
Common Name English
ETHYNODIOL DIACETATE [USP IMPURITY]
Common Name English
ETYNODIOL DIACETATE [MART.]
Common Name English
NSC-759288
Code English
Etynodiol diacetate [WHO-DD]
Common Name English
ETHYNODIOL DIACETATE [USAN]
Common Name English
SC 11800
Code English
KELNOR COMPONENT ETHYNODIOL DIACETATE
Common Name English
ETYNODIOL DIACETATE
MART.   WHO-DD  
Common Name English
SC-11800
Code English
Classification Tree Code System Code
NCI_THESAURUS C776
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
Code System Code Type Description
RXCUI
4170
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID4020614
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
DRUG BANK
DB00823
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
EVMPD
SUB02051MIG
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
CAS
297-76-7
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
NSC
759288
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200624
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
MERCK INDEX
m5179
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
206-044-9
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
NCI_THESAURUS
C47525
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
RS_ITEM_NUM
1268003
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
PUBCHEM
9270
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
IUPHAR
7072
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
WIKIPEDIA
Etynodiol diacetate
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
MESH
D005040
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
DAILYMED
62H10A1236
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
FDA UNII
62H10A1236
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
SMS_ID
100000090167
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
CHEBI
31580
Created by admin on Fri Dec 15 15:02:22 GMT 2023 , Edited by admin on Fri Dec 15 15:02:22 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY