5-Androstenedione

5-Androstenedione, also known as androst-5-ene-3,17-dione, is a prohormone of testosterone. The World Anti-Doping Agency prohibits its use in athletes. In the United States, it is a controlled substance.

5-Androstenedione

Clinical data
Other names	Androst-5-ene-3,17-dione; Δ5-Androstenedione; NSC-12873
Routes of administration	Oral
Identifiers
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
CAS Number	571-36-8 Y
PubChem CID	160531
DrugBank	DB01456
ChemSpider	141063
UNII	HEE11L5C3G
ChEBI	CHEBI:83865
ChEMBL	ChEMBL1743203
Chemical and physical data
Formula	C19H26O2
Molar mass	286.415 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@@H](CC=C4CC(=O)CC[C@]34C)[C@@H]1CCC2=O
InChI 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 Y Key:SQGZFRITSMYKRH-QAGGRKNESA-N Y

5-Androstenedione is structurally similar to 4-androstenedione, with the exception of the position of a carbon-carbon double bond.

4-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]

5-Androstenedione is on the World Anti-Doping Agency's list of prohibited substances,^[3] and is therefore banned from use in most major sports.

References

1. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, et al. (January 2011). "DrugBank 3.0: a comprehensive resource for 'omics' research on drugs". Nucleic Acids Research. 39 (Database issue): D1035–D1041. doi:10.1093/nar/gkq1126. PMC 3013709. PMID 21059682.
2. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, et al. (January 2008). "DrugBank: a knowledgebase for drugs, drug actions and drug targets". Nucleic Acids Research. 36 (Database issue): D901–D906. doi:10.1093/nar/gkm958. PMC 2238889. PMID 18048412.
3. "The World Anti-Doping Code: The 2020 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 2019-12-28.

External links

• 5-Androstenedione