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.
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| IUPAC name
17β-Hydroxyandrost-4-ene-3,11-dione
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| 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
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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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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
editReferences
edit- ^ Nelson RF (2005). An introduction to behavioral endocrinology. Sunderland, Mass: Sinauer Associates. p. 143. ISBN 0-87893-617-3.
- ^ 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.
- ^ 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.