19-norandrostenedione

Identification

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Name
19-norandrostenedione
Accession Number
DB01434
Type
Small Molecule
Groups
Experimental, 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
3D
Similar Structures
Synonyms
  • delta,4-Estrene-3,17-dione
  • delta4-Estrene-3,17-dione
External IDs
NSC-12164
Categories
UNII
U90987PVU5
CAS number
734-32-7
Weight
Average: 272.382
Monoisotopic: 272.177630012
Chemical Formula
C18H24O2
InChI Key
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[8.7.0.0²,⁷.0¹¹,¹⁵]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]

Pharmacology

Indication

The claim that supplemental 19-norandrostenedione has anabolic effects is unsubstantiated.

Pharmacodynamics
Not Available
Mechanism of action

19-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]

Absorption

Absorption appears variable, but some absorption does occur.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

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

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AldosteroneThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Aldosterone.
Beclomethasone dipropionateThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Beclomethasone dipropionate.
BetamethasoneThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Betamethasone.
Betamethasone phosphateThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Betamethasone phosphate.
BudesonideThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Budesonide.
Capromab pendetide19-norandrostenedione may decrease effectiveness of Capromab pendetide as a diagnostic agent.
CiclesonideThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Ciclesonide.
ClobetasolThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Clobetasol.
Clocortolone acetateThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Clocortolone acetate.
CloprednolThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Cloprednol.
Food Interactions
Not Available

References

General References
  1. Diel P, Friedel A, Geyer H, Kamber M, Laudenbach-Leschowsky U, Schanzer W, Schleipen B, Thevis M, Vollmer G, Zierau O: The prohormone 19-norandrostenedione displays selective androgen receptor modulator (SARM) like properties after subcutaneous administration. Toxicol Lett. 2008 Apr 1;177(3):198-204. doi: 10.1016/j.toxlet.2008.01.014. Epub 2008 Feb 2. [PubMed:18325697]
External Links
KEGG Compound
C14500
PubChem Compound
92834
PubChem Substance
46505377
ChemSpider
83803
ChEBI
34187
PDRhealth
PDRhealth Drug Page
Wikipedia
19-Norandrostenedione

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 Solubility0.0454 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 RuleNoChemAxon
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 inhibitorNon-inhibitor0.9269
CYP450 2D6 inhibitorNon-inhibitor0.94
CYP450 2C19 inhibitorNon-inhibitor0.7094
CYP450 3A4 inhibitorNon-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
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
GC-MS Spectrum - EI-BGC-MSsplash10-00di-2950000000-5865fd40ca280de239b7
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-4-steroids / 17-oxosteroids / Delta-4-steroids / Cyclohexenones / Organic oxides / Hydrocarbon derivatives
Substituents
Estrogen-skeleton / Oxosteroid / 17-oxosteroid / 3-oxosteroid / 3-oxo-delta-4-steroid / Delta-4-steroid / Cyclohexenone / Cyclic ketone / Ketone / Organic oxygen compound
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3-oxo steroid (CHEBI:34187)

Drug created on July 24, 2007 14:36 / Updated on April 21, 2019 06:05