5-Androstenedione

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5-Androstenedione
5-Androstenedione.svg
Clinical data
Other namesAndrost-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
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC19H26O2
Molar mass286.415 g·mol−1
3D model (JSmol)
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 checkY
  • Key:SQGZFRITSMYKRH-QAGGRKNESA-N checkY

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 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, 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.
  2. ^ 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.
  3. ^ "The World Anti-Doping Code: The 2020 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 2019-12-28.

External links[]


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