Androstendione

Androstenedione
Clinical data


Synonyms	A4; Δ⁴-dione; Androstenedione; Androst-4-ene-3,17-dione; 4-Androstene-3,17-dione; 17-Ketotestosterone; 17-Oxotestosterone
ATC code	None
Legal status
Legal status	US: Schedule III
Pharmacokinetic data
Metabolism	Liver
Identifiers
IUPAC name 4-Androstene-3,17-dione
CAS Number	63-05-8^Y
PubChem CID	6128
IUPHAR/BPS	2860
DrugBank	DB01536^Y
ChemSpider	5898^Y
UNII	409J2J96VR
ChEBI	CHEBI:16422^Y
ChEMBL	CHEMBL274826^Y
ECHA InfoCard	100.000.504
Chemical and physical data
Formula	C₁₉H₂₆O₂
Molar mass	286.4 g/mol
3D model (JSmol)	Interactive image
Melting point	173–174 °C (343–345 °F)
SMILES O=C4/C=C3/CC[C@@H]2[C@H](CC[C@@]1(C(=O)CC[C@H]12)C)[C@@]3(C)CC4
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^Y Key:AEMFNILZOJDQLW-QAGGRKNESA-N^Y

Androstenedione, or 4-androstenedione (abbreviated as A4 or Δ⁴-dione), also known as androst-4-ene-3,17-dione, is an endogenous weak androgen steroid hormone and intermediate in the biosynthesis of testosterone from dehydroepiandrosterone (DHEA) and of estrone. It is closely related to androstenediol (androst-5-ene-3β,17β-diol).

Androstenedione is a precursor of testosterone and other androgens, as well as of estrogens like estrone, in the body. In addition to functioning as an endogenous prohormone, androstenedione also has weak androgenic activity in its own right.

Androstenedione has been found to possess some estrogenic activity, similarly to other DHEA metabolites. However, in contrast to androstenediol, its affinity for the estrogen receptors is very low, with less than 0.01% of the affinity of estradiol for both the ERα and ERβ.

In children aged 6 to 8 years old, there is a rise in androstenedione secretion along with DHEA during adrenarche. This rise in androstenedione and DHEA is hypothesized to play a crucial role for learning social, cultural and ecological skills, such as the development and understanding of sexual attraction. Furthermore, it is thought that androstenedione plays a role in levels of aggression and competition in boys, as a positive correlation between the two were observed, while testosterone levels were below detection.

Androstenedione is the common precursor of the androgen and estrogen sex hormones.

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Wikipedia