Identification

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Name
5-androstenedione
Accession Number
DB01456
Type
Small Molecule
Groups
Experimental, Illicit
Description

5-androstenedione is a prohormone of testosterone. In the United States, the Controlled Substance Act is inclusive to anabolic steroids and their precursors. Thus 5-androstenedione is a controlled substance, and its use in athletes is prohibited by The World Anti-Doping Agency. Apart from the positioning of a carbon-carbon double bond, its structure is similar to 4-androstenedione, which is a prohormone which is naturally produced in the body by the adrenal glands and gonads, and acts as precursor to testosterone, as well as estrone and estradiol.

Structure
Thumb
Synonyms
  • 5-Androstene-3,17-dione
  • androst-5-ene-3,17-dione
  • delta5-Androstene-3,17-dione
External IDs
J79.661A / NSC-12873
Categories
UNII
HEE11L5C3G
CAS number
571-36-8
Weight
Average: 286.415
Monoisotopic: 286.193280077
Chemical Formula
C19H26O2
InChI Key
SQGZFRITSMYKRH-QAGGRKNESA-N
InChI
InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3,14-16H,4-11H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
IUPAC Name
(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,14-dione
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2CC(=O)CC[C@]12C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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
Not Available
Affected organisms
Not Available
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.
DrugInteraction
AldosteroneThe risk or severity of edema formation can be increased when 5-androstenedione is combined with Aldosterone.
Beclomethasone dipropionateThe risk or severity of edema formation can be increased when 5-androstenedione is combined with Beclomethasone dipropionate.
BetamethasoneThe risk or severity of edema formation can be increased when 5-androstenedione is combined with Betamethasone.
Betamethasone phosphateThe risk or severity of edema formation can be increased when 5-androstenedione is combined with Betamethasone phosphate.
BudesonideThe risk or severity of edema formation can be increased when 5-androstenedione is combined with Budesonide.
Capromab pendetide5-androstenedione may decrease effectiveness of Capromab pendetide as a diagnostic agent.
CiclesonideThe risk or severity of edema formation can be increased when 5-androstenedione is combined with Ciclesonide.
ClobetasolThe risk or severity of edema formation can be increased when 5-androstenedione is combined with Clobetasol.
Clocortolone acetateThe risk or severity of edema formation can be increased when 5-androstenedione is combined with Clocortolone acetate.
CloprednolThe risk or severity of edema formation can be increased when 5-androstenedione is combined with Cloprednol.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0062415
KEGG Compound
C20252
PubChem Compound
160531
PubChem Substance
46507159
ChemSpider
141063
ChEBI
83865
ChEMBL
CHEMBL1743203
Wikipedia
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 Solubility0.0366 mg/mLALOGPS
logP3.21ALOGPS
logP3.57ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)16.23ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.63 m3·mol-1ChemAxon
Polarizability33.23 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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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 androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Androstane steroids
Direct Parent
Androgens and derivatives
Alternative Parents
3-oxo delta-5-steroids / 17-oxosteroids / Delta-5-steroids / Cyclic ketones / Organic oxides / Hydrocarbon derivatives
Substituents
Androgen-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
17-oxo steroid, androstanoid, 3-oxo Delta(5)-steroid (CHEBI:83865)

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Sevrioukova IF, Poulos TL: Structure and mechanism of the complex between cytochrome P4503A4 and ritonavir. Proc Natl Acad Sci U S A. 2010 Oct 26;107(43):18422-7. doi: 10.1073/pnas.1010693107. Epub 2010 Oct 11. [PubMed:20937904]

Drug created on July 31, 2007 07:09 / Updated on November 02, 2019 00:50