11-Ketotestosterone

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11-Ketotestosterone

IUPAC name 17-Hydroxyandrost-4-ene-3,11-dione
Other names 11-Ketotestosterone; 11-Oxotestosterone
Identifiers
CAS number	53187-98-7
PubChem	104796
ChemSpider	4445528^Y
Jmol-3D images	Image 1 Image 2
SMILES 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
InChI 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^Y Key: WTPMRQZHJLJSBO-XQALERBDSA-N^Y 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
Properties
Molecular formula	C₁₉H₂₆O₃
Molar mass	302.40794
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

11-Ketotestosterone is an oxidized form of testosterone that contains a keto group at position-11. 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]

References

^ Nelson, Randy F. (2005). An introduction to behavioral endocrinology. Sunderland, Mass: Sinauer Associates. pp. 143. ISBN 0-87893-617-3.
^ Nagahama Y, Miura T, Kobayashi T (1994). "The onset of spermatogenesis in fish". Ciba Found. Symp. 182: 255–67; discussion 267–70. PMID 7835154.

Androgenics

Receptor

AR (A, B)

Agonists:
1-Androstenediol
1-Testosterone
1,4-Androstenedione
4-Androstenediol
4-Chlordehydromethyltestosterone
4-Hydroxytestosterone
5-Androstenediol
5α-Androst-1-ene-3,17-dione
11-Ketotestosterone
17-((1-Oxoheptyl)oxy)androstan-3-one
17-((1-Oxopentyl)oxy)androstan-3-one
17-(1-Oxopropoxy)androstan-3-one
17β-Hydroxyandrost-2-ene-2-carbonitrile
19-Norandrostenediol
19-Norandrostenedione
19-Norandrosterone
19-Nordehydrotestosterone
Adrenosterone
Androisoxazole
Androstanolone
Bolandiol
Bolasterone
Bolazine
Boldenone
Boldione
Bolenol
Bolmantalate
Calusterone
Clostebol
Cloxotestosterone
Danazol
Desogestrel
Desoxymethyltestosterone
DHT
Drostanolone
Enestebol
Epitiostanol
Ethisterone
Ethyldienolone
Ethylestrenol
Fluoxymesterone
Formebolone
Furazabol
Hexabolan
Hydroxystenozole
Levonorgestrel
Mebolazine
Mepitiostane
Mesabolone
Mestanolone
Mesterolone
Metandienone/Methandrostenolone
Metenolone
Metenolone acetate
Metenolone enanthate
Methandriol
Methandriol propionate
Methasterone
Methylestrenolone
Methyltestosterone
Metribolone
Mibolerone
Nandrolone
Nandrolone caproate
Nandrolone cypionate
Nandrolone cyclohexane carboxylate
Nandrolone cyclohexylpropionate
Nandrolone cyclotate
Nandrolone decanoate
Nandrolone furylpropionate
Nandrolone hexyloxyphenylpropionate
Nandrolone hydrogen succinate
Nandrolone laurate
Nandrolone phenylpropionate
Nandrolone propionate
Nandrolone undecyclate
Norbolethone
Norclostebol
Norethandrolone
Norethisterone
Norgestrel
Oxabolone
Oxabolone cypionate
Oxandrolone
Oxendolone
Oxymesterone
Oxymetholone
Penmesterol
Propetandrol
Quinbolone
Roxibolone
Silandrone
Stanozolol
Stenbolone
Stenbolone acetate
Testolactone
Testosterone
Testosterone enanthate
Testosterone ketolaurate
Testosterone nicotinate
Testosterone propionate
Testosterone undecanoate
THG
Thiomesterone
Tibolone
Tiomesterone
Trenbolone
Trenbolone acetate
Trestolone

Note: Anabolic steroids, including those that are only weakly virilizing (or even anti-virilizing (e.g., oxandrolone)), are included here (since their anabolic effects are nonetheless mediated via activation of the androgen receptor).

Antagonists:
ARN-509
Benorterone
Bicalutamide
BMS-641,988
BOMT
Canrenoic acid
Canrenone
Chlormadinone
Chlormadinone acetate
Cioteronel
Cyproterone
Cyproterone acetate
Delanterone
Dienogest
Estradiol
Flutamide
Galeterone
Hydroxyflutamide
Hydroxyprogesterone caproate
Inocoterone
MDV3100
Medroxyprogesterone
Medroxyprogesterone acetate
Megestrol
Megestrol acetate
Metogest
Nilutamide
Nomegestrol
Nordinone
Norgestimate
Osaterone
Oxendolone
Potassium canrenoate
Progesterone
R2956
Rosterolone
Spironolactone
Topterone
Zanoterone

Enzyme
(inhibitors)

20,22-Desmolase	22-ABC 3,3′-Dimethoxybenzidine 3-Methoxybenzidine Aminoglutethimide Cyanoketone Danazol Etomidate Trilostane

17α-Hydroxylase, 17,20-Lyase	22-ABC 22-Oxime Abiraterone Bifonazole Clotrimazole Cyanoketone Cyproterone Danazol Desogestrel Econazole Galeterone Gestrinone Isoconazole Ketoconazole L-39 Levonorgestrel Liarozole LY-207,320 MDL-27,302 Miconazole Mifepristone Norethisterone Orteronel Pioglitazone Rosiglitazone Spironolactone Stanozolol SU-10,603 Tioconazole TGF-β Troglitazone VN/87-1 YM116

3β-HSD (I, II)	4-MA Azastene Cyanoketone Danazol Desogestrel Epostane Genistein Gestrinone Levonorgestrel Medroxyprogesterone Medroxyprogesterone acetate Metyrapone Norethisterone Oxymetholone Pioglitazone Rosiglitazone Trilostane Troglitazone

17β-HSD (I-XIV)	Danazol Simvastatin

5α-Reductase (I, II)	22-Oxime Alfatradiol Azelaic acid β-Sitosterol Bexlosteride Dutasteride Epristeride Finasteride Izonsteride L-39 Lapisteride Polyunsaturated fatty acids (α-linolenic acid, linoleic acid, γ-linolenic acid, oleic acid) Turosteride Vitamin B6 Zinc

Aromatase	1,4,6-Androstatriene-3,17-dione 4-Androstene-3,6,17-trione 4-Cyclohexylaniline 4-Hydroxytestosterone 5α-DHNET Abyssinone II Aminoglutethimide Anastrozole Ascorbic acid (Vitamin C) Atamestane Bifonazole CGP-45,688 CGS-47,645 Clotrimazole DHT Difeconazole Econazole Exemestane Fadrozole Fenarimol Finrozole Formestane Imazalil Isoconazole Ketoconazole Letrozole Liarozole MEN-11066 Miconazole Minamestane Nimorazole NKS01 Norethindrone ORG-33,201 Penconazole Plomestane Prochloraz Propioconazole Pyridoglutethimide Rogletimide Rotenone Talarozole Testolactone Tioconazole Triadimefon Triadimenol Troglitazone Vorozole YM511 Zinc Note: 21-Hydroxylase inhibitors may also affect androgen levels as they prevent metabolism of androgen steroid precursors.

Other

Precursors	Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone 17-Hydroxypregnenolone Progesterone 17-Hydroxyprogesterone Cortodoxone DHEA DHEA sulfate Androstenediol Androstenedione

Indirect	Estrogens/Antiestrogens (see here) GnRH agonists/antagonists (see here) Gonadotropins (see here) Plasma proteins (SHBG, ABP, Albumin) Progestogens/Antiprogestins (see here) Prolactin

Procedures	Adrenalectomy Hypophysectomy Oophorectomy Orchiectomy

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Wikipedia on Answers.com This article is licensed under the Creative Commons Attribution/Share-Alike License. It uses material from the Wikipedia article 11-Ketotestosterone. Read