11-Ketotestosterone

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-cyclopenta[a]phenanthrene-7,10-dione
Other names
11-Ketotestosterone; 11-Oxotestosterone
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • 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/s1 checkY
    Key: WTPMRQZHJLJSBO-XQALERBDSA-N checkY
  • 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/s1
    Key: WTPMRQZHJLJSBO-XQALERBDBO
  • CC12CCC(=O)C=C1CCC3C2C(=O)CC4(C3CCC4O)C
  • O=C2C[C@]4([C@H]([C@@H]3CC\C1=C\C(=O)CC[C@]1(C)[C@@H]23)CC[C@@H]4O)C
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).
☒N verify (what is checkY☒N ?)

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] 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).[3] 11-Ketoandrostenedione has notably been sold online as an androgen prohormone, usually under the name 11-oxoandrostenedione (11-OXO).[3]

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. ^ a b c 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.