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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomy19-norandrostenedione
Identification
- 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
Structure for 19-norandrostenedione (DB01434)
- 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
- 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.
Drug Interaction Unlock Additional DataAldosterone The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Aldosterone. Beclomethasone dipropionate The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Beclomethasone dipropionate. Betamethasone The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Betamethasone. Betamethasone phosphate The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Betamethasone phosphate. Budesonide The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Budesonide. Ciclesonide The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Ciclesonide. Clobetasol The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Clobetasol. Clocortolone acetate The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Clocortolone acetate. Cloprednol The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Cloprednol. Corticotropin The risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Corticotropin. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
References
- General References
- 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
- ZINC
- ZINC000004428372
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- 19-Norandrostenedione
Clinical Trials
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
Property Value Source Water Solubility 0.0454 mg/mL ALOGPS logP 2.53 ALOGPS logP 3.63 ChemAxon logS -3.8 ALOGPS pKa (Strongest Acidic) 19.19 ChemAxon pKa (Strongest Basic) -4.7 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 34.14 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 79.13 m3·mol-1 ChemAxon Polarizability 31.54 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.9269 CYP450 2D6 inhibitor Non-inhibitor 0.94 CYP450 2C19 inhibitor Non-inhibitor 0.7094 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key GC-MS Spectrum - EI-B GC-MS splash10-00di-2950000000-5865fd40ca280de239b7 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not 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 March 01, 2020 18:41
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