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

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

Molecular Formula	C20H28O2
Molecular Weight	300.4351
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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	Inhibitor 8,297		62000.0 nM [IC50]
Progesterone receptor 61	Agonist 2,678		0.13 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pregnancy 65	Preventing		Approved 8,429	FEMULEN

Doses

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Dose	Population	Adverse events
0.5 mg 1 times / day steady, oral Recommended	healthy, 16-47 n = 425	Disc. AE: Intermenstrual bleeding, Amenorrhoea...
0.5 mg steady, oral Recommended	healthy n = 178	Disc. AE: Nausea, Bleeding breakthrough...

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AEs

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AE	Significance	Dose	Population
Dysphoria	0.2% Disc. AE	0.5 mg 1 times / day steady, oral Recommended	healthy, 16-47 n = 425
Genital boil	0.2% Disc. AE	0.5 mg 1 times / day steady, oral Recommended	healthy, 16-47 n = 425
Hypertension	0.2% Disc. AE	0.5 mg 1 times / day steady, oral Recommended	healthy, 16-47 n = 425
Irritable	0.2% Disc. AE	0.5 mg 1 times / day steady, oral Recommended	healthy, 16-47 n = 425
Lethargy	0.2% Disc. AE	0.5 mg 1 times / day steady, oral Recommended	healthy, 16-47 n = 425

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Sourcing

Sourcing

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

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PubMed

Title	Date	PubMed
Cardiovascular birth defects and antenatal exposure to female sex hormones.	1977 Jan 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

Substance Class	Chemical
Record UNII	9E01C36A9S
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETHYNODIOL

Common Name

English

etynodiol [INN]

Common Name

English

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

Common Name

English

ETYNODIOL

Official Name

English

ESTR-4-ENE-3,17-DIOL, 17-ETHYNYL-, (3.BETA.,17.BETA.)-

Common Name

English

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Classification Tree

Code System

Code

Progestogens and estrogens, combinations

WHO-VATC

QG03FA06

Progestogens and estrogens, fixed combinations

WHO-ATC

G03FA06

Gonadal Steroid Hormones

NDF-RT

N0000011301

Birth control

LIVERTOX

385

Therapeutic Steroid Hormone

NCI_THESAURUS

C776

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Code System

Code

Type

Description

FDA UNII

9E01C36A9S

PRIMARY

EVMPD

SUB07350MIG

PRIMARY

WIKIPEDIA

Etynodiol

PRIMARY

RXCUI

24591

PRIMARY

RxNorm

ECHA (EC/EINECS)

214-971-5

PRIMARY

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Related Record

Type

Details


					3ZZ5BJ9F2Q

DIFENOXIN

METABOLITE -> PARENT

Comments:

Metabolite to parent drug ratio in non-uraemic human plasma.

Interaction Type:

METABOLITE TO PARENT DRUG RATIO

Qualification:

PLASMA; URINE

Amount:

RELATIONSHIP_AMOUNT 420 MICROGRAM/MG (average)


					3ZZ5BJ9F2Q

DIFENOXIN

METABOLITE -> PARENT

Comments:

Percent of dose excreted in urine as metabolite.

Qualification:

URINE

Amount:

RELATIONSHIP_AMOUNT 3.6 WEIGHT PERCENT (average)

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Show entries

Related Record

Type

Details


					9E01C36A9S

ETHYNODIOL

ACTIVE MOIETY

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