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11-Ketotestosterone

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11-Ketotestosterone
Names
IUPAC name 17β-Hydroxyandrost-4-ene-3,11-dione
Systematic IUPAC name (1S,3aS,3bS,9aR,9bS,11aS)-1-Hydroxy-9a,11a-dimethyl-2,3,3a,3b,4,5,8,9,9a,9b,11,11a-dodecahydro-1H-cyclopentaphenanthrene-7,10-dione
Other names 11-Ketotestosterone; 11-Oxotestosterone
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C19H26O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-14,16-17,22H,3-8,10H2,1-2H3/t13-,14-,16-,17+,18-,19-/m0/s1Key: WTPMRQZHJLJSBO-XQALERBDSA-N
  • InChI=1/C19H26O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-14,16-17,22H,3-8,10H2,1-2H3/t13-,14-,16-,17+,18-,19-/m0/s1Key: WTPMRQZHJLJSBO-XQALERBDBO
SMILES
  • CC12CCC(=O)C=C1CCC3C2C(=O)CC4(C3CCC4O)C
  • O=C2C4((3CC\C1=C\C(=O)CC1(C)23)CC4O)C
Properties
Chemical formula C19H26O3
Molar mass 302.40794
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

11-Ketotestosterone (11-KT) is an oxidized form of testosterone that contains a keto group at the C11 position. It is related to adrenosterone, an androgen found in trace quantities in humans. In fish, 11-ketotestosterone functions as the endogenous androgenic sex hormone. In midshipman fish, 11-ketotestosterone is not present in females or Type II Males — Type II Males reach sexual maturation later, are less territorial, and have higher testosterone than Type I Males.

In mammals, 11-ketotestosterone has similar potency to testosterone as an androgen, and has been identified as an important adrenal androgen. However, unlike testosterone, it is very weakly anabolic and mostly prevents muscle breakdown as opposed to promoting muscle growth. It is synthesized from 11β-hydroxyandrostenedione and, to a lesser extent, 11-ketoandrostenedione (adrenosterone). 11-Ketoandrostenedione has notably been sold online as an androgen prohormone, usually under the name 11-oxoandrostenedione (11-OXO).

See also

References

  1. Nelson RF (2005). An introduction to behavioral endocrinology. Sunderland, Mass: Sinauer Associates. p. 143. ISBN 0-87893-617-3.
  2. Nagahama Y, Miura T, Kobayashi T (1994). "The Onset of Spermatogenesis in Fish". Germline Development. Ciba Foundation Symposium. Vol. 182. pp. 255–67, discussion 267–70. doi:10.1002/9780470514573.ch14. ISBN 9780470514573. PMID 7835154.
  3. ^ Pretorius E, Arlt W, Storbeck KH (February 2017). "A new dawn for androgens: Novel lessons from 11-oxygenated C19 steroids" (PDF). Molecular and Cellular Endocrinology. 441: 76–85. doi:10.1016/j.mce.2016.08.014. PMID 27519632. S2CID 4079662.
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