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19-Nor-5-androstenedione

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Overview

Structure
DrugBank ID
DB01443
Type
Small Molecule
US Approved
NO
Other Approved
NO
Patents
0
Indicated Conditions
0
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
19-Nor-5-androstenedione
DrugBank Accession Number
DB01443
Background

19-Nor-5-andorstenedione is a prohormone which has the potential to affect bodily levels of testosterone once metabolized in vivo. It is regulated in the United States as a schedule III controlled substance, and prohibited by the World Anti-Doping Agency for use in competitive sports.

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 272.388
Monoisotopic: 272.177630013
Chemical Formula
C18H24O2
Synonyms
  • estr-5-ene-3,17-dione
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

It is believed that 19-Nor-5-andorstenedione may be metabolized in the body to produce a metabolite which can activate the androgen receptor, similar to testosterone. However, androgen receptor activation is likely less than that of testosterone or dihydrotestosterone.

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

Because 19-Nor-5-androstenedione is metabolically related to other controlled anabolic steroids, it is likely to have similar adverse health effects such as liver, heart and skin problems, hormonal disruptions, stunted growth, and psychological effects such as rage and depression.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available
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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

Drug Categories
Not Available
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-oxo delta-5-steroids / 17-oxosteroids / Delta-5-steroids / Cyclic ketones / Organic oxides / Hydrocarbon derivatives
Substituents
17-oxosteroid / 3-oxo-delta-5-steroid / 3-oxosteroid / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic ketone / Delta-5-steroid / Estrogen-skeleton / Hydrocarbon derivative / Ketone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
585LQ9KZN8
CAS number
19289-77-1
InChI Key
WELNRNVZXWUOGT-QXUSFIETSA-N
InChI
InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2,13-16H,3-10H2,1H3/t13-,14+,15+,16-,18-/m0/s1
IUPAC Name
(3aS,3bR,9aR,9bS,11aS)-11a-methyl-1H,2H,3H,3aH,3bH,4H,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-dione
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)CC3=CC[C@@]21[H]

References

General References
Not Available
PubChem Compound
18633059
PubChem Substance
46508864
ChemSpider
18612511
Wikipedia
19-Nor-5-androstenedione

Clinical Trials

Clinical Trials
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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 Solubility0.0621 mg/mLALOGPS
logP3.09ALOGPS
logP3.27Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)16.25Chemaxon
pKa (Strongest Basic)-7.2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area34.14 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity79.16 m3·mol-1Chemaxon
Polarizability31.58 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-0090000000-0775e291bbd2753bbee3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-5970747764bd1391238c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0490000000-b35b1bf0e1929b689c83
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-fba7aaffa63c8e9c4220
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-2900000000-9aa445fc04ae383ca361
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-91d1a1788aaf588e38f0
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]-173.83669
predicted
DeepCCS 1.0 (2019)
[M+H]+176.19467
predicted
DeepCCS 1.0 (2019)
[M+Na]+183.06798
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:09 / Updated at June 12, 2020 16:51