5-Androstenedione

5-Androstenedione
Clinical data
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;
Synonyms	Androst-5-ene-3,17-dione; Δ5-Androstenedione; NSC-12873
CAS Number	571-36-8 ;
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
3D model (Jmol)	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 ; Key:SQGZFRITSMYKRH-QAGGRKNESA-N ;

5-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.

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]

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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Clinical data

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
Synonyms	Androst-5-ene-3,17-dione; Δ⁵-Androstenedione; NSC-12873
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
3D model (Jmol)	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