11-Ketotestosterone

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11-Ketotestosterone
11-Ketotestosterone.svg
Names
IUPAC name
17-Hydroxyandrost-4-ene-3,11-dione
Other names
11-Ketotestosterone; 11-Oxotestosterone
Identifiers
3D model (JSmol)
ChemSpider
Properties
C19H26O3
Molar mass 302.40794
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[1][2] 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.[3] It is synthesized from 11β-hydroxyandrostenedione and, to a lesser extent, 11-ketoandrostenedione (adrenosterone).[3] 11-Ketoandrostenedione has notably been sold online as an androgen prohormone, usually under the name 11-oxoandrostenedione (11-OXO).[3]

References[edit]

  1. ^ Nelson, Randy F. (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". Ciba Found. Symp. 182: 255–67; discussion 267–70. PMID 7835154. 
  3. ^ a b c Pretorius, Elzette; Arlt, Wiebke; Storbeck, Karl-Heinz (2016). "A new dawn for androgens: Novel lessons from 11-oxygenated C19 steroids". Molecular and Cellular Endocrinology. ISSN 0303-7207. PMID 27519632. doi:10.1016/j.mce.2016.08.014.