This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Ethynodiol
Accession Number
DB13866
Type
Small Molecule
Groups
Experimental
Description

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

Structure
Thumb
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
  • etinodiol
  • étynodiol
  • Etynodiol
  • etynodiolum
Categories
UNII
9E01C36A9S
CAS number
1231-93-2
Weight
Average: 300.442
Monoisotopic: 300.208930142
Chemical Formula
C20H28O2
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]

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbciximabEthynodiol may decrease the anticoagulant activities of Abciximab.
AcenocoumarolEthynodiol may decrease the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidEthynodiol may decrease the anticoagulant activities of Acetylsalicylic acid.
AlclometasoneThe serum concentration of Alclometasone can be increased when it is combined with Ethynodiol.
AlfuzosinThe metabolism of Ethynodiol can be decreased when combined with Alfuzosin.
AlteplaseEthynodiol may decrease the anticoagulant activities of Alteplase.
AmcinonideThe serum concentration of Amcinonide can be increased when it is combined with Ethynodiol.
AmiodaroneThe metabolism of Ethynodiol can be decreased when combined with Amiodarone.
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Ethynodiol.
AmoxicillinThe metabolism of Ethynodiol can be increased when combined with Amoxicillin.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D07939
PubChem Compound
14687
PubChem Substance
347829321
ChemSpider
14017
ChEBI
50785
ChEMBL
CHEMBL1201406
Wikipedia
Etynodiol
ATC Codes
G03FA06 — Etynodiol and estrogenG03DC06 — EtynodiolG03AA01 — Etynodiol and ethinylestradiol

Clinical Trials

Clinical Trials
Not Available

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
PropertyValueSource
Water Solubility0.00785 mg/mLALOGPS
logP2.61ALOGPS
logP2.81ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)17.52ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity88.32 m3·mol-1ChemAxon
Polarizability35.26 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

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
Estrogen-skeleton / 3-hydroxy-delta-4-steroid / 3-hydroxysteroid / 17-hydroxysteroid / 3-beta-hydroxysteroid / Hydroxysteroid / Delta-4-steroid / Ynone / Cyclic alcohol / Tertiary alcohol
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
terminal acetylenic compound, 3beta-hydroxy steroid, 17beta-hydroxy steroid (CHEBI:50785)

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Gene labs [Link]

Drug created on July 04, 2017 15:13 / Updated on August 02, 2018 07:00