4-androstenedione

4-Androstenedione
Clinical data


ATC code	none
Legal status
Legal status	Schedule III (US)
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^Y
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 (Jmol)	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

Δ⁴-Androstenedione (abbreviated as Δ⁴-dione), commonly referred to simply as androstenedione, and also known as androst-4-ene-3,17-dione, 4-androstene-3,17-dione or 17-ketotestosterone, is an endogenous androgen steroid hormone and intermediate in the biosynthesis of testosterone from dehydroepiandrosterone (DHEA). In turn, Δ⁴-dione is also a precursor of dihydrotestosterone (DHT), estrogens such as estradiol and estrone, and the neurosteroid 3α-androstanediol.

Δ⁴-Dione is the common precursor of the androgen and estrogen sex hormones.

Δ⁴-Dione can be biosynthesized in one of two ways. The primary pathway involves conversion of 17α-hydroxypregnenolone to DHEA by way of 17,20-lyase, with subsequent conversion of DHEA to Δ⁴-dione via the enzyme 3β-hydroxysteroid dehydrogenase. The secondary pathway involves conversion of 17α-hydroxyprogesterone, most often a precursor to cortisol, to Δ⁴-dione directly by way of 17,20-lyase. Thus, 17,20-lyase is required for the synthesis of Δ⁴-dione, whether immediately or one step removed.

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Wikipedia