4-Hydroxytestosterone

4-Hydroxytestosterone
Names


IUPAC name 4,17-Dihydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
Other names 4,17β-Dihydroxy-4-androstene-3-one; (17β)-4,17-dihydroxyandrost-4-en-3-one
Identifiers
CAS Number	2141-17-5^N
ChemSpider	141138^Y
DrugBank	DB01485^Y
Jmol interactive 3D	Image
PubChem	160615
UNII	912GOZ167T^N
InChI InChI=1S/C19H28O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,16,21-22H,3-10H2,1-2H3/t11-,12-,13-,16-,18+,19-/m0/s1^Y Key: BQOIJSIMMIDHMO-FBPKJDBXSA-N^Y InChI=1/C19H28O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,16,21-22H,3-10H2,1-2H3/t11-,12-,13-,16-,18+,19-/m0/s1 Key: BQOIJSIMMIDHMO-FBPKJDBXBD
SMILES O=C4C(\O)=C2/[C@]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)(C)CC4
Properties
Chemical formula	C₁₉H₂₈O₃
Molar mass	304.42 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

4-Hydroxytestosterone (4-OHT), also known as 4,17β-dihydroxy-4-androstene-3-one, is an anabolic steroid. It was first patented by G.D. Searle & Company in 1955 and is testosterone with a hydroxy group at the four position. 4-OHT has moderate anabolic, mild androgenic, and anti-aromatase properties and is similar to the steroid clostebol.

References

Anabolic steroids (A14)

Androstane (carbon 19 present)	Adrenosterone Androisoxazole Bolasterone (Myagen) Bolazine Boldione Boldenone undecylenate (Equipoise) 4-Chlordehydromethyltestosterone (Turinabol) 4-Hydroxytestosterone Calusterone Clostebol Danazol Desoxymethyltestosterone (Madol) DHT Drostanolone (Masteron) Enestebol Epitiostanol Fluoxymesterone (Halotestin) Formebolone Furazabol (Miotolan) Hydroxystenozole Mebolazine Mesabolone Mestanolone Mesterolone (Proviron) Metandienone (methandrostenolone) Methandriol Metenolone Methenolone enanthate (Primobolan) Methasterone (Superdrol) Methyltestosterone Methyldiazirinol Oxandrolone (Anavar) Oxymetholone (Anadrol) Oxymesterone Prostanozol Quinbolone (Anabolicum Vister) Roxibolone Silandrone Stanozolol (Strombafort Winstrol) Stenbolone Testosterone`s (Sustamed Sustanon) 1-Testosterone Thiomesterone

Estrene (carbon 19 absent)	Bolenol Ethyldienolone Ethylestrenol Mibolerone (Cheque Drops) Metribolone (R1881) Nandrolone (Deca Durabolin) Norboletone (Genabol) Norclostebol Norethandrolone Normethandrone (methylestrenolone) Oxabolone cipionate Propetandrol Tetrahydrogestrinone (The Clear) Trenbolone (Fina) Trestolone

Prohormones	1-Androstenediol 1,4-Androstadienedione 4-Androstenediol 4-Androstenedione 19-Norandrostenediol 19-Norandrostenedione DHEA

Androgenics

Receptor
(ligands)

Agonists	4-Chlordehydromethyltestosterone 4-Hydroxytestosterone 5α-Androst-1-ene-3,17-dione 7β-Hydroxyepiandrosterone 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 Δ¹-Androstenediol Δ¹-Testosterone Δ^1,4-Androstenedione Δ⁴-Androstenediol Δ⁴-Androstenedione Δ^4-Tibolone Δ⁴-Androstenediol Δ⁴-Androstenedione Adrenosterone Androisoxazole Androstanolone Bolandiol Bolasterone Bolazine Boldenone Boldione Bolenol Bolmantalate Calusterone Cl-4AS-1 Clostebol Cloxotestosterone Cortexolone 17α-propionate Danazol Desogestrel Desoxymethyltestosterone DHEA DHEA sulfate Dihydrotestosterone Drostanolone Enestebol Epitiostanol Ethisterone Ethyldienolone Ethylestrenol Fluoxymesterone Formebolone Furazabol Hexabolan Hydroxystenozole Levonorgestrel Mebolazine Medroxyprogesterone acetate 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 Norboletone Norclostebol Norethandrolone Norethisterone Norgestrel Oxabolone Oxabolone cypionate Oxandrolone Oxendolone Oxymesterone Oxymetholone Penmesterol Propetandrol Quinbolone Quingestanol acetate Roxibolone Silandrone Stanozolol Stenbolone Stenbolone acetate Testolactone Testosterone Testosterone acetate Testosterone capropate Testosterone cypionate Testosterone decanoate Testosterone enanthate Testosterone isocaproate Testosterone ketolaurate Testosterone nicotinate Testosterone phenylpropionate Testosterone propionate Testosterone undecanoate Tetrahydrogestrinone Thiomesterone Tibolone Tiomesterone Trenboloneca Trenbolone acetate Trestolone

Mixed (SARMs)	AC-262,356 Andarine BMS-564,929 Enobosarm (ostarine) LGD-2226 LGD-3303 LGD-4033 RAD140 S-23 S-40503 TFM-4AS-1

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone Abiraterone Abiraterone acetate Apalutamide AZD-3514 Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S) Benorterone Bicalutamide BMS-641,988 BOMT Canrenoic acid Canrenone Chlormadinone acetate Cimetidine Cioteronel Clometerone Cyproterone Cyproterone acetate Delanterone DDT (via metabolite p,p’-DDE) Dieldrin Dienogest Drospirenone Endosulfan Enzalutamide EPI-001 Epitestosterone Fenarimol Flutamide Galeterone Guggulsterone Hydroxyflutamide Inocoterone Ketoconazole Lavender oil Linuron Megestrol acetate Mespirenone Methiocarb Metogest Mifepristone Nilutamide Nomegestrol Nordinone Norgestimate ODM-201 ONC1-13B ORM-15341 Osaterone Oxendolone PF-998425 Potassium canrenoate Prochloraz Procymidone R-2956 Rosterolone RU-58642 RU-58841 Spironolactone Topilutamide (fluridil) Topterone Valproic acid Vinclozolin VT-464 Zanoterone

Enzyme

Modulators	See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 17β-HSD, 5α-reductase, and aromatase).

Others

Precursors/prohormones	Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone Pregnenolone sulfate 17-Hydroxypregnenolone Progesterone 17-Hydroxyprogesterone 11-Deoxycortisol (cortodoxone) DHEA DHEA sulfate Δ⁵-Androstenediol Δ⁴-Androstenedione

Indirect	Antigonadotropins (e.g., estrogens, progestogens, prolactin) GnRH agonists (e,g, GnRH, leuprorelin) GnRH antagonists (e.g., cetrorelix) Gonadotropins (e.g., FSH, hCG, LH) Kisspeptin Plasma proteins (ABP, albumin, SHBG)

See also: Estrogenics • Glucocorticoids • Mineralocorticoids • Progestogenics

Steroid hormone metabolism modulators

20,22-Desmolase	Inhibitors: 22-ABC 3,3′-Dimethoxybenzidine 3-Methoxybenzidine Aminoglutethimide Canrenone Cyanoketone Danazol Etomidate Ketoconazole Mitotane Spironolactone Trilostane

17α-Hydroxylase, 17,20-Lyase	Inhibitors: 22-ABC 22-Oxime Abiraterone Abiraterone acetate Bifonazole Canrenone CFG-920 Clotrimazole Cyanoketone Cyproterone acetate Danazol Econazole Galeterone Gestrinone Isoconazole Ketoconazole L-39 Liarozole LY-207,320 MDL-27,302 Miconazole Mifepristone Orteronel Pioglitazone Prochloraz Rosiglitazone Spironolactone Stanozolol SU-10,603 TGF-β Tioconazole Troglitazone VN/87-1 VT-464 YM116

3α-HSD	Inhibitors: Coumestrol Daidzein Genistein Indomethacin Medroxyprogesterone acetate Inducers: Fluoxetine Fluvoxamine Mirtazapine Paroxetine Sertraline Venlafaxine

3β-HSD	Inhibitors: 4-MA Abiraterone Abiraterone acetate Azastene Cyanoketone Cyproterone acetate Danazol Epostane Genistein Gestrinone Metyrapone Norethisterone Oxymetholone Pioglitazone Rosiglitazone Trilostane Troglitazone

11β-HSD	Inhibitors: 18α-Glycyrrhizic acid ABT-384 Acetoxolone Carbenoxolone Enoxolone (glycyrrhetinic acid) Epigallocatechin gallate Glycyrrhizin (glycyrrhizic acid)

21-Hydroxylase	Inhibitors: Aminoglutethimide Amphenone B Bifonazole Canrenone Clotrimazole Diazepam Econazole Genistein Isoconazole Ketoconazole Metyrapone Miconazole Midazolam Spironolactone Tioconazole

11β-Hydroxylase	Inhibitors: Abiraterone Abiraterone acetate Aminoglutethimide Canrenone Etomidate Fadrozole FETO Ketoconazole Metomidate Metyrapone Mitotane Potassium canrenoate Spironolactone Trilostane

18-Hydroxylase	Inhibitors: Aminoglutethimide Canrenone FAD286 Fadrozole Ketoconazole LCI699 Metyrapone Mespirenone Potassium canrenoate Spironolactone

17β-HSD	Inhibitors: Danazol Simvastatin

5α-Reductase	Inhibitors: 22-Oxime Alfatradiol Azelaic acid β-Sitosterol Bexlosteride Chlormadinone acetate Cl-4AS-1 Dutasteride Epitestosterone Epristeride Fatty acids (α-linolenic acid, linoleic acid, γ-linolenic acid, monolinolein, oleic acid) Finasteride Ganoderic acid Izonsteride L-39 Lapisteride Saw palmetto TFM-4AS-1 Turosteride Vitamin B6 Zinc

Aromatase	Inhibitors: 4-AT 4-Cyclohexylaniline 4-Hydroxytestosterone 5α-DHNET Abyssinone II Aminoglutethimide Anastrozole Ascorbic acid (vitamin C) Atamestane ATD Bifonazole CGP-45,688 CGS-47,645 Chalconoids (e.g., isoliquiritigenin) Corynesidone A Clotrimazole DHT Difeconazole Econazole Ellagitannins Endosulfan Exemestane Fadrozole Fatty acids (e.g., conjugated linoleic acid, linoleic acid, linolenic acid, palmitic acid) Fenarimol Finrozole Flavonoids (e.g., 7-hydroxyflavone, 7-hydroxyflavanone, 7,8-DHF, acacetin, apigenin, baicalein, biochanin A, chrysin, EGCG, gossypetin, hesperetin, liquiritigenin, myricetin, naringenin, pinocembrin, rotenone, quercetin, sakuranetin, tectochrysin) Formestane Imazalil Isoconazole Ketoconazole Letrozole Liarozole Melatonin MEN-11066 Miconazole Minamestane Nimorazole NKS01 Norendoxifen ORG-33,201 Penconazole Phenytoin Prochloraz PGE2 (dinoprostone) Plomestane Prochloraz Propioconazole Pyridoglutethimide Quinolinoids (e.g., berberine, casimiroin, triptoquinone A, XHN22, XHN26, XHN27) Resorcylic acid lactones (e.g., zearalenone) Rogletimide Stilbenoids (e.g., resveratrol) Talarozole Terpenoids (e.g., dehydroabietic acid, (–)-dehydrololiolide, retinol (vitamin A), Δ⁹-THC, tretinoin) Testolactone Tioconazole Triadimefon Triadimenol Troglitazone Valproic acid Vorozole Xanthones (e.g., garcinone D, garcinone E, α-mangostin, γ-mangostin, monodictyochrome A, monodictyochrome B) YM-511 Zinc Inducers: Atrazine Flavonoids (e.g., genistein, quercetin)

27-Hydroxylase	Inhibitors: Anastrozole Bicalutamide Dexmedetomidine Fadrozole Posaconazole Ravuconazole

See also: Androgenics • Estrogenics • Glucocorticoidics • Mineralocorticoidics • Progestogenics

This article is issued from Wikipedia - version of the Thursday, December 31, 2015. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.