From Wikipedia, the free encyclopedia
Chemical compound
5-Androstenedione
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Other names | Androst-5-ene-3,17-dione; Δ5-Androstenedione; NSC-12873 |
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Routes of administration |
Oral |
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(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
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CAS Number | |
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PubChem
CID | |
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DrugBank | |
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ChemSpider | |
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UNII | |
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ChEBI | |
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ChEMBL | |
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Formula | C19H26O2 |
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Molar mass | 286.415 g·mol−1 |
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3D model (
JSmol) | |
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C[C@]12CC[C@H]3[C@@H](CC=C4CC(=O)CC[C@]34C)[C@@H]1CCC2=O
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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 YKey:SQGZFRITSMYKRH-QAGGRKNESA-N Y
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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
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^ 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.
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^
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.
-
^
"The World Anti-Doping Code: The 2020 Prohibited List" (PDF).
World Anti-Doping Agency. Retrieved 2019-12-28.
External links
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ARTooltip Androgen receptor | Agonists | |
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SARMsTooltip Selective androgen receptor modulator | |
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Antagonists | |
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GPRC6A | |
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CARTooltip Constitutive androstane receptor | |
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PXRTooltip Pregnane X receptor | |
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