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
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
Molecular Formula | C20H28O2 |
Molecular Weight | 300.4351 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including http://nwpeu.de/media/wysiwyg/PDFs/Femulen_PIL_.pdf
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14065347
Curator's Comment: Now is a part of Pfizer.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL6020 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28340509 |
62000.0 nM [IC50] | ||
Target ID: P06401 Gene ID: 5241.0 Gene Symbol: PGR Target Organism: Homo sapiens (Human) |
0.13 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | FEMULEN Approved UseFemulen helps to prevent you becoming pregnant. |
Doses
Dose | Population | Adverse 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%) Sources: 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%) |
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 |
Disc. AE: Nausea, Bleeding breakthrough... AEs leading to discontinuation/dose reduction: Nausea (0.6%) Sources: Bleeding breakthrough (1.1%) Mastopathy (2.8%) Dysmenorrhoea (3.9%) Neuropathy (3.9%) Headache (1.1%) Abnormal weight gain (0.6%) Thrombophlebitis (0.6%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
Sample Use Guides
In Vivo Use Guide
Sources: http://nwpeu.de/media/wysiwyg/PDFs/Femulen_PIL_.pdf
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:04:05 GMT 2023
by
admin
on
Fri Dec 15 15:04:05 GMT 2023
|
Record UNII |
9E01C36A9S
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
Metabolite to parent drug ratio in non-uraemic human plasma.
METABOLITE TO PARENT DRUG RATIO
PLASMA; URINE
|
||
|
METABOLITE -> PARENT |
Percent of dose excreted in urine as metabolite.
URINE
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |