NAV

Ethylestrenol

Identification

Generic Name
Ethylestrenol
DrugBank Accession Number
DB01493
Background

An anabolic steroid with some progestational activity and little androgenic effect. [PubChem]

Type
Small Molecule
Groups
Withdrawn
Structure
3D
Similar Structures
Weight
Average: 288.4675
Monoisotopic: 288.245315646
Chemical Formula
C20H32O
Synonyms
  • Ethylestrenol
  • etilestrenol
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Pharmacology

Indication

Not Available

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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.
Not Available
Food Interactions
Not Available

Categories

ATC Codes
A14AB02 — Ethylestrenol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pregnane steroids. These are steroids with a structure based on the 21-carbon pregnane skeleton.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Pregnane steroids
Alternative Parents
17-hydroxysteroids / Delta-4-steroids / Tertiary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
17-hydroxysteroid / Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Delta-4-steroid / Hydrocarbon derivative / Hydroxysteroid / Organic oxygen compound / Organooxygen compound / Pregnane-skeleton
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
tertiary alcohol, 17beta-hydroxy steroid (CHEBI:31578)
Affected organisms
Not Available

Chemical Identifiers

UNII
ADC79EK5Q8
CAS number
965-90-2
InChI Key
AOXRBFRFYPMWLR-XGXHKTLJSA-N
InChI
InChI=1S/C20H32O/c1-3-20(21)13-11-18-17-9-8-14-6-4-5-7-15(14)16(17)10-12-19(18,20)2/h6,15-18,21H,3-5,7-13H2,1-2H3/t15-,16+,17+,18-,19-,20-/m0/s1
IUPAC Name
(1S,3aS,3bR,9aR,9bS,11aS)-1-ethyl-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-ol
SMILES
[H][C@@]12CC[C@@](O)(CC)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCCC=C3CC[C@@]21[H]

References

Synthesis Reference

Szpilfogel, S.A. and de Winter, M.S.; U.S. Patent 2,878,267; March 17, 1959; assigned to Organon Inc. Szpilfogel, S.A., Hanegraaf, J.A. and van Dijck, L.A.; U.S. Patent 3,112,328; Nov. 26, 1963 assigned to Organon Inc.

General References
Not Available
PubChem Compound
13765
PubChem Substance
46505460
ChemSpider
13168
RxNav
4162
ChEBI
31578
ChEMBL
CHEMBL1200623
ZINC
ZINC000004215863
PharmGKB
PA449539
Wikipedia
Ethylestrenol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)about 50Szpilfogel, S.A. and de Winter, M.S.; U.S. Patent 2,878,267; March 17, 1959; assigned to Organon Inc. Szpilfogel, S.A., Hanegraaf, J.A. and van Dijck, L.A.; U.S. Patent 3,112,328; Nov. 26, 1963 assigned to Organon Inc.
Predicted Properties
PropertyValueSource
Water Solubility0.00086 mg/mLALOGPS
logP5.2ALOGPS
logP4.69Chemaxon
logS-5.5ALOGPS
pKa (Strongest Basic)-0.27Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area20.23 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity88.5 m3·mol-1Chemaxon
Polarizability35.94 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9876
Caco-2 permeable+0.8415
P-glycoprotein substrateSubstrate0.6943
P-glycoprotein inhibitor IInhibitor0.5427
P-glycoprotein inhibitor IINon-inhibitor0.8205
Renal organic cation transporterNon-inhibitor0.7538
CYP450 2C9 substrateNon-substrate0.8322
CYP450 2D6 substrateNon-substrate0.9092
CYP450 3A4 substrateSubstrate0.7296
CYP450 1A2 substrateNon-inhibitor0.8767
CYP450 2C9 inhibitorNon-inhibitor0.8723
CYP450 2D6 inhibitorNon-inhibitor0.9163
CYP450 2C19 inhibitorNon-inhibitor0.6126
CYP450 3A4 inhibitorNon-inhibitor0.7518
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5395
Ames testNon AMES toxic0.9436
CarcinogenicityNon-carcinogens0.9323
BiodegradationNot ready biodegradable0.9786
Rat acute toxicity1.8534 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7664
hERG inhibition (predictor II)Non-inhibitor0.6561
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dr-0090000000-2d93d93f373f853a6ee3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-e5efc571d7156bf39d14
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-2d634fad3c234309de53
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-1290000000-48e9e92f08dfda7dd724
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-fe912bbb2856f356a99d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9600000000-223ec03bc30d2c0474ed
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-179.3057716
predicted
DarkChem Lite v0.1.0
[M-H]-174.30498
predicted
DeepCCS 1.0 (2019)
[M+H]+179.6054716
predicted
DarkChem Lite v0.1.0
[M+H]+176.70055
predicted
DeepCCS 1.0 (2019)
[M+Na]+179.2808716
predicted
DarkChem Lite v0.1.0
[M+Na]+183.25311
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:09 / Updated at February 21, 2021 18:51