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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
SaltsNot Available
Brand names
NameCompany
19-N-AndroNot Available
BolandioneNot Available
Proven Pure 19-NorandrostenedioneNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number734-32-7
WeightAverage: 272.382
Monoisotopic: 272.177630012
Chemical FormulaC18H24O2
InChI KeyInChIKey=JRIZOGLBRPZBLQ-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[8.7.0.0^{2,7}.0^{11,15}]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]
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassKetosteroids
Direct parentKetosteroids
Alternative parentsEstrogens and Derivatives; Ketones; Polyamines
Substituentsketone; polyamine; carbonyl group
Classification descriptionThis compound belongs to the ketosteroids. These are steroid derivatives comprising a ketone group attached to steroid skeleton.
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
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9723
Caco-2 permeable + 0.7785
P-glycoprotein substrate Substrate 0.5551
P-glycoprotein inhibitor I Inhibitor 0.8097
P-glycoprotein inhibitor II Non-inhibitor 0.6972
Renal organic cation transporter Non-inhibitor 0.638
CYP450 2C9 substrate Non-substrate 0.827
CYP450 2D6 substrate Non-substrate 0.9064
CYP450 3A4 substrate Substrate 0.6816
CYP450 1A2 substrate Non-inhibitor 0.8259
CYP450 2C9 substrate Non-inhibitor 0.9269
CYP450 2D6 substrate Non-inhibitor 0.94
CYP450 2C19 substrate Non-inhibitor 0.7094
CYP450 3A4 substrate Non-inhibitor 0.8652
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7931
Ames test Non AMES toxic 0.9189
Carcinogenicity Non-carcinogens 0.9403
Biodegradation Not ready biodegradable 0.9401
Rat acute toxicity 1.6104 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.7011
hERG inhibition (predictor II) Non-inhibitor 0.7574
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
PowderOral
TabletOral
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility4.54e-02 g/lALOGPS
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 area34.14ChemAxon
rotatable bond count0ChemAxon
refractivity79.13ChemAxon
polarizability31.54ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
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
ResourceLink
KEGG CompoundC14500
PubChem Compound92834
PubChem Substance46505377
ChemSpider83803
PDRhealthhttp://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/19n_0010.shtml
Wikipedia19-Norandrostenedione
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
Drug created on July 24, 2007 14:36 / Updated on September 16, 2013 17:14