ETHYNODIOL

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 Search

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=C[C@@H](O)CC[C@H]34)[C@@H]1CC[C@@]2(O)C#C

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
Sources: http://www.glowm.com/section_view/heading/Metabolic%20and%20Endocrinologic%20Effects%20of%20Steroidal%20Contraception/item/388
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bile salt export pump 15 Target ID: CHEMBL6020 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28340509	Inhibitor 8504		62000.0 nM [IC50]
Progesterone receptor 61 Target ID: P06401 Gene ID: 5241.0 Gene Symbol: PGR Target Organism: Homo sapiens (Human) Sources: http://www.glowm.com/section_view/heading/Metabolic%20and%20Endocrinologic%20Effects%20of%20Steroidal%20Contraception/item/388	Agonist 2752		0.13 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pregnancy 65 Sources: http://nwpeu.de/media/wysiwyg/PDFs/Femulen_PIL_.pdf	Preventing		Approved 8583	FEMULEN Approved Use Femulen helps to prevent you becoming pregnant.

C_max

Value	Dose	Co-administered	Analyte	Population
174.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7445531	0.15 mg/kg single, intragastric dose: 0.15 mg/kg route of administration: Intragastric experiment type: SINGLE co-administered:		ETHYNODIOL plasma	Macaca mulatta population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
6731 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7445531	0.15 mg/kg single, intragastric dose: 0.15 mg/kg route of administration: Intragastric experiment type: SINGLE co-administered:		ETHYNODIOL plasma	Macaca mulatta population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
43.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7445531	0.15 mg/kg single, intragastric dose: 0.15 mg/kg route of administration: Intragastric experiment type: SINGLE co-administered:		ETHYNODIOL plasma	Macaca mulatta population: HEALTHY age: ADULT sex: MALE food status: FASTED

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: https://pubmed.ncbi.nlm.nih.gov/3297483/	healthy, 16-47 Health Status: healthy Age Group: 16-47 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/3297483/	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: https://pubmed.ncbi.nlm.nih.gov/3297483/
0.5 mg steady, oral Recommended Dose: 0.5 mg Route: oral Route: steady Dose: 0.5 mg Sources: https://pubmed.ncbi.nlm.nih.gov/4870629/	healthy Health Status: healthy Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/4870629/	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: https://pubmed.ncbi.nlm.nih.gov/4870629/

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:50785	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:50785
eMolecules	30152728	https://www.emolecules.com/cgi-bin/more?vid=30152728
ZINC	ZINC000030691629	http://zinc15.docking.org/substances/ZINC000030691629

PubMed

Title	Date	PubMed
Cardiovascular birth defects and antenatal exposure to female sex hormones.	1977-01-13	830309

Patents

Sample Use Guides

In Vivo Use Guide

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

ETYNODIOL

Preferred Name

English

ETHYNODIOL

Common Name

English

etynodiol [INN]

Common Name

English

17.ALPHA.-ETHYNYL-4-OESTRENE-3.BETA.,17.BETA.-DIOL

Common 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