Etynodiol

Identification

Generic Name

Etynodiol

DrugBank Accession Number

DB13866

Background

Etynodiol (INN), or ethynodiol (BAN) is a steroidal progestin related to norethisterone which was never marketed. While etynodiol is sometimes used as a synonym for etynodiol diacetate, it usually refers to etynodiol diacetate (see Ethynodiol diacetate), not etynodiol.

Type

Small Molecule

Groups

Experimental

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Etynodiol (DB13866)

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Weight

Average: 300.442
Monoisotopic: 300.208930142

Chemical Formula

C₂₀H₂₈O₂

Synonyms

• (3β,17α)-19-Norpregn-4-en-20-yne-3,17-diol
• 17α-Ethynyl-19-norandrost-4-ene-3β,17β-diol
• 3β-hydroxynorethisterone
• Aethynodiolum
• Ethinodiol
• Ethynodiol
• Etinodiol
• étynodiol
• Etynodiol
• Etynodiolum

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

Not Available

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abametapir	The serum concentration of Etynodiol can be increased when it is combined with Abametapir.
Abciximab	The therapeutic efficacy of Abciximab can be decreased when used in combination with Etynodiol.
Acenocoumarol	The therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Etynodiol.
Acetaminophen	The metabolism of Etynodiol can be increased when combined with Acetaminophen.
Acetazolamide	The metabolism of Etynodiol can be increased when combined with Acetazolamide.
Acetohexamide	The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Etynodiol.
Alpelisib	The metabolism of Etynodiol can be increased when combined with Alpelisib.
Alteplase	The therapeutic efficacy of Alteplase can be decreased when used in combination with Etynodiol.
Aminoglutethimide	The metabolism of Etynodiol can be increased when combined with Aminoglutethimide.
Amiodarone	The metabolism of Etynodiol can be decreased when combined with Amiodarone.

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Food Interactions

Not Available

Categories

ATC Codes

G03DC06 — Etynodiol

• G03DC — Estren derivatives
• G03D — PROGESTOGENS
• G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
• G — GENITO URINARY SYSTEM AND SEX HORMONES

G03FA06 — Etynodiol and estrogen

• G03FA — Progestogens and estrogens, fixed combinations
• G03F — PROGESTOGENS AND ESTROGENS IN COMBINATION
• G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
• G — GENITO URINARY SYSTEM AND SEX HORMONES

G03AA01 — Etynodiol and ethinylestradiol

• G03AA — Progestogens and estrogens, fixed combinations
• G03A — HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
• G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
• G — GENITO URINARY SYSTEM AND SEX HORMONES

Drug Categories

• Adrenal Cortex Hormones
• Cytochrome P-450 CYP3A Substrates
• Cytochrome P-450 CYP3A4 Substrates
• Cytochrome P-450 Substrates
• Estren Derivatives
• Fused-Ring Compounds
• Genito Urinary System and Sex Hormones
• Hormonal Contraceptives for Systemic Use
• Norpregnanes
• Norpregnenes
• Norsteroids
• Progestins
• Sex Hormones and Modulators of the Genital System
• Steroids

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens and derivatives

Alternative Parents

3-hydroxy delta-4-steroids / 3-beta-hydroxysteroids / 17-hydroxysteroids / Delta-4-steroids / Ynones / Tertiary alcohols / Secondary alcohols / Cyclic alcohols and derivatives / Acetylides / Hydrocarbon derivatives

Substituents

17-hydroxysteroid / 3-beta-hydroxysteroid / 3-hydroxy-delta-4-steroid / 3-hydroxysteroid / Acetylide / Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Delta-4-steroid / Estrogen-skeleton

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

terminal acetylenic compound, 3beta-hydroxy steroid, 17beta-hydroxy steroid (CHEBI:50785)

Affected organisms

Not Available

Chemical Identifiers

UNII

9E01C36A9S

CAS number

1231-93-2

InChI Key

JYILPERKVHXLNF-QMNUTNMBSA-N

InChI

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

IUPAC Name

(1S,2R,5S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-diol

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CC[C@H](O)C=C3CC[C@@]21[H]

References

General References

Not Available

External Links

KEGG Drug

D07939

PubChem Compound

14687

PubChem Substance

347829321

ChemSpider

14017

RxNav

24591

ChEBI

50785

ChEMBL

CHEMBL1201406

ZINC

ZINC000030691629

Wikipedia

Etynodiol

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00785 mg/mL	ALOGPS
logP	2.61	ALOGPS
logP	2.81	Chemaxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	17.52	Chemaxon
pKa (Strongest Basic)	-1.4	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	40.46 Å2	Chemaxon
Rotatable Bond Count	0	Chemaxon
Refractivity	88.32 m3·mol-1	Chemaxon
Polarizability	35.26 Å3	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Not Available

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Drug created at July 04, 2017 21:13 / Updated at February 21, 2021 18:54