DrugBank: 4-Androstenedione (DB01536)

targets (4)

Identification

Name

4-Androstenedione

Accession Number

DB01536 (DB07386, EXPT00569)

Type

small molecule

Groups

illicit, experimental

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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

4-Androstene-3,17-dione

Brand names

Not Available

Brand name mixtures

Not Available

Categories

Not Available

CAS number

63-05-8

Weight

Average: 286.4085
Monoisotopic: 286.193280076

Chemical Formula

C₁₉H₂₆O₂

InChI Key

InChIKey=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

Plain Text

IUPAC Name

(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]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

Plain Text

Mass Spec

show (11.2 KB)

Taxonomy

Kingdom

Not Available

Classes

Steroids and Steroid Derivatives

Substructures

Steroids and Steroid Derivatives
Carbonyl Compounds
Alkanes and Alkenes
Cyclohexenes and Derivatives
Ketones

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.

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

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Melting point

Not Available

Experimental Properties

Property	Value	Source
logS	-3.69 [ADME Research, USCD]	PhysProp

Predicted Properties

Property	Value	Source
water solubility	2.70e-02 g/l	ALOGPS
logP	2.93	ALOGPS
logP	3.93	ChemAxon Molconvert
logS	-4.03	ALOGPS
pKa		ChemAxon Molconvert
hydrogen acceptor count	2	ChemAxon Molconvert
hydrogen donor count	0	ChemAxon Molconvert
polar surface area	34.14	ChemAxon Molconvert
rotatable bond count	0	ChemAxon Molconvert
refractivity	83.61	ChemAxon Molconvert
polarizability	33.20	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D00051
KEGG Compound	C00280
PubChem Compound	6128
PubChem Substance	46508011
ChemSpider	5898
ChEBI	16422
ChEMBL	16422
HET	ASD
Drug Product Database	0

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

1XF0

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Drug	Interaction

Food Interactions

Not Available

Targets
1. Estradiol 17-beta-dehydrogenase 1 Pharmacological action: yes Actions: inducer Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH Organism class: human UniProt ID: P14061 Gene: HSD17B1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 I Pharmacological action: yes Actions: positive allosteric modulator 3beta-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 3beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids Organism class: human UniProt ID: P14060 Gene: HSD3B1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 Pharmacological action: unknown Actions: inducer Conversion of 6-deoxyerythronolide B (6-DEB) to erythronolide B (EB) by the insertion of an oxygen at the 6S position of 6-DEB Organism class: bacterial UniProt ID: Q00441 Gene: eryF Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 Pharmacological action: unknown Actions: inducer Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9alpha,11beta- PGF2 to PGD2. Functions as a bi-directional 3alpha-, 17beta- and 20alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone Organism class: human UniProt ID: P42330 Gene: AKR1C3 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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

Targets

1. Estradiol 17-beta-dehydrogenase 1

Pharmacological action: yes
Actions: inducer

Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH

Organism class: human
UniProt ID: P14061 Link_out

Gene: HSD17B1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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 I

Pharmacological action: yes
Actions: positive allosteric modulator

3beta-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 3beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids

Organism class: human
UniProt ID: P14060 Link_out

Gene: HSD3B1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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

Pharmacological action: unknown
Actions: inducer

Conversion of 6-deoxyerythronolide B (6-DEB) to erythronolide B (EB) by the insertion of an oxygen at the 6S position of 6-DEB

Organism class: bacterial
UniProt ID: Q00441 Link_out

Gene: eryF
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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

Pharmacological action: unknown
Actions: inducer

Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9alpha,11beta- PGF2 to PGD2. Functions as a bi-directional 3alpha-, 17beta- and 20alpha HSD. Can interconvert active androgens, estrogens and progestins with their cognate inactive metabolites. Preferentially transforms androstenedione (4-dione) to testosterone

Organism class: human
UniProt ID: P42330 Link_out

Gene: AKR1C3 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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

Comments

Drug created on June 13, 2005 07:24 / Updated on October 11, 2011 10:58

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.