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Identification
Name4-Androstenedione
Accession NumberDB01536  (DB07386, EXPT00569)
TypeSmall Molecule
GroupsExperimental, 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. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
4-Androstene-3,17-dioneNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number63-05-8
WeightAverage: 286.4085
Monoisotopic: 286.193280076
Chemical FormulaC19H26O2
InChI KeyAEMFNILZOJDQLW-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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • Oxosteroid
  • 17-oxosteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of action4-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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
Pathways
PathwayCategorySMPDB ID
Androgen and Estrogen MetabolismMetabolicSMP00068
Aromatase deficiencyDiseaseSMP00565
17-Beta Hydroxysteroid Dehydrogenase III DeficiencyDiseaseSMP00356
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.9387
CYP450 2D6 substrateNon-inhibitor0.9386
CYP450 2C19 substrateNon-inhibitor0.8138
CYP450 3A4 substrateNon-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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point158 °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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (11.2 KB)
SpectraGC-MSMS/MSMS1D NMR2D NMR
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 ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Estradiol 17-beta-dehydrogenase 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inducer

Components

Name UniProt ID Details
Estradiol 17-beta-dehydrogenase 1 P14061 Details

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
  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

2. 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: positive allosteric modulator

Components

Name UniProt ID Details
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1 P14060 Details

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

3. 6-deoxyerythronolide B hydroxylase

Kind: protein

Organism: Saccharopolyspora erythraea (strain NRRL 23338)

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
6-deoxyerythronolide B hydroxylase Q00441 Details

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
  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

4. Aldo-keto reductase family 1 member C3

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Aldo-keto reductase family 1 member C3 P42330 Details

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
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:15