11-Ketotestosterone

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| Verifiedfields = changed

| verifiedrevid = 477208815

| ImageFile = 11-Ketotestosterone.svg

| ImageSize = 250

| IUPACName = 17β-Hydroxyandrost-4-ene-3,11-dione

| SystematicName = (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

| OtherNames = 11-Ketotestosterone; 11-Oxotestosterone

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4445528

| 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

| InChIKey = WTPMRQZHJLJSBO-XQALERBDBO

| SMILES1 = 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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = WTPMRQZHJLJSBO-XQALERBDSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 564-35-2

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = KF38W1A85U

| PubChem = 104796

| SMILES = CC12CCC(=O)C=C1CCC3C2C(=O)CC4(C3CCC4O)C

}}

| Section2 = {{Chembox Properties

| Formula = C₁₉H₂₆O₃

| MolarMass = 302.40794

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| Section3 = {{Chembox Hazards

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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.{{cite book | vauthors = Nelson RF | title = An introduction to behavioral endocrinology | publisher = Sinauer Associates | location = Sunderland, Mass | year = 2005 | pages = 143 | isbn = 0-87893-617-3 }}{{cite book |vauthors=Nagahama Y, Miura T, Kobayashi T | title = Germline Development | chapter = The Onset of Spermatogenesis in Fish | series = Ciba Foundation Symposium | volume = 182 | pages = 255–67; discussion 267–70 | year = 1994 | pmid = 7835154 | doi = 10.1002/9780470514573.ch14 | isbn = 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.{{cite journal | vauthors = Pretorius E, Arlt W, Storbeck KH | title = A new dawn for androgens: Novel lessons from 11-oxygenated C19 steroids | journal = Molecular and Cellular Endocrinology | volume = 441 | pages = 76–85 | date = February 2017 | pmid = 27519632 | doi = 10.1016/j.mce.2016.08.014 | s2cid = 4079662 | url = 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).