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
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
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QG03FA06
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WHO-ATC |
G03FA06
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NDF-RT |
N0000011301
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LIVERTOX |
385
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NCI_THESAURUS |
C776
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WHO-VATC |
QG03AA01
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WHO-VATC |
QG03DC06
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WHO-ATC |
G03DC06
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WHO-ATC |
G03AA01
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NDF-RT |
N0000175602
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9E01C36A9S
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SUB07350MIG
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Etynodiol
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24591
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214-971-5
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m5179
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100000082137
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1231-93-2
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C014546
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C72771
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ACTIVE MOIETY
METABOLITE (PARENT)