5-Androstenedione

5-Androstenedion
Names
	IUPAC name (8R,9S,10R,13S,14S)-10,13-Dimethyl-2,4,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
	Systematic IUPAC name Androst-5-ene-3,17-dione
	Other names 5-Androsten-3,17-dione; NSC 12873; Δ5-Androstene-3,17-dione
Identifiers
CAS Number	571-36-8
ChemSpider	141063
DrugBank	DB01456
Jmol 3D model	Interactive image
PubChem	160531
	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/h3,14-16H,4-11H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1 Key: SQGZFRITSMYKRH-QAGGRKNESA-N ; InChI=1/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/h3,14-16H,4-11H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1 Key: SQGZFRITSMYKRH-QAGGRKNEBS ;
	SMILES C[C@]12CC[C@H]3[C@@H](CC=C4CC(=O)CC[C@]34C)[C@@H]1CCC2=O ;
Properties
Chemical formula	C19H26O2
Molar mass	286.42 g·mol−1
Vapor pressure	{{{value}}}
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Δ⁵-Androstenedione is a prohormone of testosterone. The World Anti-Doping Agency prohibits its use in athletes. In the United States, it is a controlled substance.

Δ⁵-Androstenedione is structurally similar to Δ⁴-androstenedione, with the exception of the position of a carbon-carbon double bond. Δ⁴-Androstenedione is naturally produced in the body by the adrenal glands and gonads. In addition to testosterone, it is also a precursor of estrone and estradiol.^[1]^[2]

References

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