11-Ketotestosterone

vanc changed 477208815 11-Ketotestosterone.svg skin-invert-image 250 17β-Hydroxyandrost-4-ene-3,11-dione (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 11-Ketotestosterone; 11-Oxotestosterone correct chemspider 4445528 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 WTPMRQZHJLJSBO-XQALERBDBO 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 correct chemspider 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 correct chemspider WTPMRQZHJLJSBO-XQALERBDSA-N correct CAS 564-35-2 correct FDA KF38W1A85U 104796 CC12CCC(=O)C=C1CCC3C2C(=O)CC4(C3CCC4O)C C19H26O3 302.40794 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. Nelson RF An introduction to behavioral endocrinology Sinauer Associates Sunderland, Mass 2005 143 0-87893-617-3 Nagahama Y, Miura T, Kobayashi T Germline Development The Onset of Spermatogenesis in Fish Ciba Foundation Symposium 182 255–67; discussion 267–70 1994 7835154 10.1002/9780470514573.ch14 9780470514573 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. Pretorius E, Arlt W, Storbeck KH A new dawn for androgens: Novel lessons from 11-oxygenated C19 steroids Molecular and Cellular Endocrinology 441 76–85 February 2017 27519632 10.1016/j.mce.2016.08.014 4079662 http://pure-oai.bham.ac.uk/ws/files/30346231/Pretorius_et_al_manuscript.pdf 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 Testosterone 11β-Hydroxytestosterone References 2 Category:Secondary alcohols Category:Androgens Category:Androstanes Category:Hormones of the suprarenal cortex Category:Cyclic ketones Category:Sex hormones Category:Steroid hormones Category:Hydroxy ketones