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
	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[edit]

^ Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS (2011). "DrugBank 3.0: a comprehensive resource for omics research on drugs". Nucleic Acids Res. 39 (Database issue): D1035–41. doi:10.1093/nar/gkq1126. PMC 3013709. PMID 21059682.
^ Wishart, David S.; Knox, Craig; Guo, An Chi; Cheng, Dean; Shrivastava, Savita; Tzur, Dan; Gautam, Bijaya; Hassanali, Murtaza (2008). "DrugBank: a knowledgebase for drugs, drug actions and drug targets". Nucleic Acids Research. 36 (Database issue): D901–6. doi:10.1093/nar/gkm958. PMC 2238889. PMID 18048412.

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