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Identification
Name19-norandrostenedione
Accession NumberDB01434
TypeSmall Molecule
GroupsExperimental, Illicit
Description

19-Norandrostenedione refers to two steroid isomers that were once marketed as dietary supplements and mainly used by body builders. After 2005, 19-Norandrostenedione was regulated in the United States as a schedule III controlled substance, as well as banned from use in competitive sports by the World Anti-Doping Agency.

In the body 19-norandrostenedione is rapidly metabolized into nandrolone, also known as nortestosterone.

Structure
Thumb
Synonyms
SynonymLanguageCode
4-estrene-3,17-dioneNot AvailableNot Available
delta4-Estrene-3,17-dioneNot AvailableNot Available
NORNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
19-N-AndroNot Available
BolandioneNot Available
Proven Pure 19-NorandrostenedioneNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number734-32-7
WeightAverage: 272.382
Monoisotopic: 272.177630012
Chemical FormulaC18H24O2
InChI KeyJRIZOGLBRPZBLQ-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/h10,13-16H,2-9H2,1H3/t13-,14+,15+,16-,18-/m0/s1
IUPAC Name
(1S,2R,10R,11S,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-ene-5,14-dione
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationThe claim that supplemental 19-norandrostenedione has anabolic effects is unsubstantiated.
PharmacodynamicsNot Available
Mechanism of action19-Norandrostenedione may be metabolized to 19-nortestosterone in both men and women. 19-Norandrostenedione, also known as nandrolone, is the basic substance of some very popular injectable anabolic steroids, however 19-norandrostenedione is not metabolized to testosterone. Whether or not increases in 19-nortestosterone levels would be sustained long enough by taking 19-norandrostenedione to show an increase in nitrogen retention and muscle strength and mass is unknown. 19-Norandrostenedione has also been shown to bind to androgen receptors with high selectivity. Transactivation of androgen receptor dependent reporter gene expression was 10 times lower than that produced by dihydrotestosterone. [1]
AbsorptionAbsorption appears variable, but some absorption does occur.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Specific metabolites of 19-nor-5-androstene-3, 17-dione are 19-nordehydroandrosterone and 19-nordehydroepiandrosterone.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9723
Caco-2 permeable+0.7785
P-glycoprotein substrateSubstrate0.5551
P-glycoprotein inhibitor IInhibitor0.8097
P-glycoprotein inhibitor IINon-inhibitor0.6972
Renal organic cation transporterNon-inhibitor0.638
CYP450 2C9 substrateNon-substrate0.827
CYP450 2D6 substrateNon-substrate0.9064
CYP450 3A4 substrateSubstrate0.6816
CYP450 1A2 substrateNon-inhibitor0.8259
CYP450 2C9 substrateNon-inhibitor0.9269
CYP450 2D6 substrateNon-inhibitor0.94
CYP450 2C19 substrateNon-inhibitor0.7094
CYP450 3A4 substrateNon-inhibitor0.8652
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7931
Ames testNon AMES toxic0.9189
CarcinogenicityNon-carcinogens0.9403
BiodegradationNot ready biodegradable0.9401
Rat acute toxicity1.6104 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7011
hERG inhibition (predictor II)Non-inhibitor0.7574
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0454 mg/mLALOGPS
logP2.53ALOGPS
logP3.63ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)19.19ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.13 m3·mol-1ChemAxon
Polarizability31.54 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference

1. Diel, P., et al. “The prohormone 19-norandrostenedione displays selective androgen receptor modulator (SARM) like properties after subcutaneous administration.” Toxicology letters 177.3 (2008): 198-204.

External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on July 24, 2007 14:36 / Updated on September 16, 2013 17:14