Identification

Name
Androstenedione
Accession Number
DB01536  (EXPT00569, DB07386)
Type
Small Molecule
Groups
Experimental, Illicit
Description

A delta-4 C19 steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol.

Structure
Thumb
Synonyms
  • 4-Androstene-3,17-dione
  • 4-Androstenedione
Categories
UNII
409J2J96VR
CAS number
63-05-8
Weight
Average: 286.4085
Monoisotopic: 286.193280076
Chemical Formula
C19H26O2
InChI Key
AEMFNILZOJDQLW-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/h11,14-16H,3-10H2,1-2H3/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-6-ene-5,14-dione
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action

4-androstenedione is a 19-carbon steroid hormone produced in the adrenal glands and the gonads as an intermediate step in the biochemical pathway that produces the androgen testosterone and the estrogens estrone and estradiol.

TargetActionsOrganism
AEstradiol 17-beta-dehydrogenase 1
inducer
Human
A3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1
positive allosteric modulator
Human
U6-deoxyerythronolide B hydroxylase
inducer
Saccharopolyspora erythraea (strain NRRL 23338)
UAldo-keto reductase family 1 member C3
inducer
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Androgen and Estrogen MetabolismMetabolic
Aromatase deficiencyDisease
Androgen and Estrogen MetabolismMetabolic
Androstenedione MetabolismMetabolic
17-beta Hydroxysteroid Dehydrogenase III DeficiencyDisease
Aromatase deficiencyDisease
Androgen and Estrogen MetabolismMetabolic
17-beta Hydroxysteroid Dehydrogenase III DeficiencyDisease
Androstenedione MetabolismMetabolic
Androgen and Estrogen MetabolismMetabolic
Androstenedione MetabolismMetabolic
Androstenedione MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limoneneThe risk or severity of adverse effects can be increased when (4R)-limonene is combined with Androstenedione.
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when Androstenedione is combined with 1,10-Phenanthroline.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Androstenedione.
AcemetacinThe risk or severity of adverse effects can be increased when Acemetacin is combined with Androstenedione.
AlclofenacThe risk or severity of adverse effects can be increased when Alclofenac is combined with Androstenedione.
AlclometasoneThe risk or severity of edema formation can be increased when Androstenedione is combined with Alclometasone.
AlfuzosinThe metabolism of Androstenedione can be decreased when combined with Alfuzosin.
AlmasilateThe bioavailability of Androstenedione can be decreased when combined with Almasilate.
AlminoprofenThe risk or severity of adverse effects can be increased when Alminoprofen is combined with Androstenedione.
AloglutamolThe bioavailability of Androstenedione can be decreased when combined with Aloglutamol.
Food Interactions
Not Available

References

Synthesis Reference

Angela M. H. Brodie, Harry J. Brodie, David A. Marsh, "Ester derivatives of 4-hydroxy-4-androstene-3,17-dione and a method for inhibiting estrogen biosynthesis." U.S. Patent US4235893, issued October, 1962.

US4235893
General References
Not Available
External Links
Human Metabolome Database
HMDB0000053
KEGG Drug
D00051
KEGG Compound
C00280
PubChem Compound
6128
PubChem Substance
46508011
ChemSpider
5898
BindingDB
91713
ChEBI
16422
ChEMBL
CHEMBL274826
HET
ASD
Wikipedia
Androstenedione
PDB Entries
1eup / 1qyx / 1xf0 / 2vct / 2vcv / 3cas / 3eqm / 3iw1 / 3nbr / 3nhx
show 13 more

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
PropertyValueSource
melting point (°C)158 °CPhysProp
water solubility57.8 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.75HANSCH,C ET AL. (1995)
logS-3.69ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.027 mg/mLALOGPS
logP2.93ALOGPS
logP3.93ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)19.03ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity83.61 m3·mol-1ChemAxon
Polarizability33.2 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+0.9793
Caco-2 permeable+0.8011
P-glycoprotein substrateSubstrate0.5526
P-glycoprotein inhibitor IInhibitor0.8564
P-glycoprotein inhibitor IINon-inhibitor0.6615
Renal organic cation transporterNon-inhibitor0.6632
CYP450 2C9 substrateNon-substrate0.8548
CYP450 2D6 substrateNon-substrate0.9131
CYP450 3A4 substrateSubstrate0.7193
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9387
CYP450 2D6 inhibitorNon-inhibitor0.9386
CYP450 2C19 inhibitorNon-inhibitor0.8138
CYP450 3A4 inhibitorNon-inhibitor0.8483
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8067
Ames testNon AMES toxic0.9508
CarcinogenicityNon-carcinogens0.9313
BiodegradationNot ready biodegradable0.9343
Rat acute toxicity1.5360 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7599
hERG inhibition (predictor II)Non-inhibitor0.7469
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (11.2 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MSGC-MSsplash10-004l-5910000000-518e1ad38bcc73325b53
GC-MS Spectrum - GC-MSGC-MSsplash10-004l-5910000000-5172e05f9889ee2bfaf4
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-000f-8940000000-f2892fe3b281d44164c8
GC-MS Spectrum - EI-BGC-MSsplash10-007d-1960000000-167f1765b095da9d603b
GC-MS Spectrum - GC-MSGC-MSsplash10-004l-5910000000-518e1ad38bcc73325b53
GC-MS Spectrum - GC-MSGC-MSsplash10-004l-5910000000-5172e05f9889ee2bfaf4
Mass Spectrum (Electron Ionization)MSsplash10-059m-3940000000-9cb32ac21e46afb2829a
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000i-0090000000-36e848ba16b141eef47b
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-052b-9600000000-712954fc35a84c8217de
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-052b-9300000000-f8e9aa16b4b208b69f7b
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-000f-8940000000-e12025ea2b7808c64b9c
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
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-052b-6910000000-b616785c86a92f46158e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-052b-9800000000-73e545a1eb2232d55371
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00kb-5790000000-735473bc44dd70e29259
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00kb-5790000000-114675a4457063901f2b
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

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-4-steroids / 17-oxosteroids / Delta-4-steroids / Cyclohexenones / Organic oxides / Hydrocarbon derivatives
Substituents
Androgen-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 Delta(4)-steroid, 17-oxo steroid, androstanoid (CHEBI:16422) / androstane, C19 steroids (androgens) and derivatives, Androstane and derivatives, Androgens (C00280) / C19 steroids (androgens) and derivatives (LMST02020007)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inducer
General Function
Testosterone dehydrogenase (nad+) activity
Specific Function
Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
Gene Name
HSD17B1
Uniprot ID
P14061
Uniprot Name
Estradiol 17-beta-dehydrogenase 1
Molecular Weight
34949.715 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Positive allosteric modulator
General Function
Steroid delta-isomerase activity
Specific Function
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system pl...
Gene Name
HSD3B1
Uniprot ID
P14060
Uniprot Name
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1
Molecular Weight
42251.25 Da
References
  1. Ishii-Ohba H, Inano H, Tamaoki B: Purification and properties of testicular 3 beta-hydroxy-5-ene-steroid dehydrogenase and 5-ene-4-ene isomerase. J Steroid Biochem. 1986 Oct;25(4):555-60. [PubMed:2945972]
Kind
Protein
Organism
Saccharopolyspora erythraea (strain NRRL 23338)
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen
Specific Function
Catalyzes the NADPH-dependent conversion of 6-deoxyerythronolide B (6-DEB) to erythronolide B (EB) by the insertion of an oxygen at the 6S position of 6-DEB. Requires the participation of a ferredo...
Gene Name
eryF
Uniprot ID
Q00441
Uniprot Name
6-deoxyerythronolide B hydroxylase
Molecular Weight
45098.685 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
Specific Function
Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2....
Gene Name
AKR1C3
Uniprot ID
P42330
Uniprot Name
Aldo-keto reductase family 1 member C3
Molecular Weight
36852.89 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Enzymes

Kind
Protein
Organism
Human
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 June 13, 2005 07:24 / Updated on August 02, 2018 04:37