19-Nor-5-androstenedione

Identification

Name
19-Nor-5-androstenedione
Accession Number
DB01443
Type
Small Molecule
Groups
Experimental, Illicit
Description

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.

Structure
Thumb
Synonyms
  • (8R,9S,10R,13S,14S)-13-Methyl-1,2,4,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione
  • (8R,9S,10R,13S,14S)-13-Methyl-1,2,4,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-quinone
  • 3β,17β-dihydroxyestr-5-ene and 3α,17β-dihydroxyestr-5-ene
  • estr-5-ene-3,17-dione
Categories
Not Available
UNII
585LQ9KZN8
CAS number
19289-77-1
Weight
Average: 272.388
Monoisotopic: 272.177630013
Chemical Formula
C18H24O2
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
(1S,2R,10R,11S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,14-dione
SMILES
C[C@]12CC[C@H]3[C@@H](CC=C4CC(=O)CC[C@H]34)[C@@H]1CCC2=O

Pharmacology

Indication
Not Available
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
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.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

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

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 Solubility0.0621 mg/mLALOGPS
logP3.09ALOGPS
logP3.27ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)16.38ChemAxon
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot 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-oxo delta-5-steroids / 17-oxosteroids / Delta-5-steroids / Cyclic ketones / Organic oxides / Hydrocarbon derivatives
Substituents
Estrogen-skeleton / Oxosteroid / 17-oxosteroid / 3-oxosteroid / 3-oxo-delta-5-steroid / Delta-5-steroid / Cyclic ketone / Ketone / Organic oxygen compound / Organic oxide
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available

Drug created on July 31, 2007 07:09 / Updated on July 02, 2018 17:33