Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/01/06 18:25:06」(JST)

wiki en

Fluoxymesterone, sold under the brand names Halotestin and Ultandren among others, is a synthetic, orally active androgenic-anabolic steroid (AAS) and a 17α-alkylated derivative of testosterone.^[1]^[2]^[3] While there are legitimate medical uses of fluoxymesterone, it is also abused, leading to the development of analytical techniques by which fluoxymesterone doping can be identified.^{[citation needed]}

Medical uses

Fluoxymesterone is or has been used in the treatment of hypogonadism in males and breast cancer in women.^{[citation needed]}

Pharmacology

Androgenic activity

Fluoxymesterone has a relatively high ratio of androgenic to anabolic activity similarly to testosterone.^{[citation needed]} Like many 17α-alkylated AAS, it has relatively low affinity for the androgen receptor (AR). However, its actions are mediated by the AR, most likely due to its relatively long elimination half-life of approximately 9.2 hours.^[4] It is approximately five times as potent as an AAS as testosterone.^[5] Unlike testosterone, fluoxymesterone has a 100% oral bioavailability, as the methylation of the C17α position of fluoxymesterone inhibits hepatic metabolism by enzymatic oxidation of 17β-hydroxyl, allowing its absorption into the bloodstream for transport around the body.^{[citation needed]}

11β-HSD inhibitor

Fluoxymesterone has been found to act as a potent inhibitor of 11β-hydroxysteroid dehydrogenase type 2 (11β-HSD2) (IC₅₀ = 60–630 nM), with a potency comparable to that of the 11β-HSD2 inhibitor glycyrrhetinic acid.^[6]^[7] This unique action of fluoxymesterone is likely related to its 11β-hydroxyl group.^[6] 11β-HSD2 is responsible for the inactivation of the glucocorticoids cortisol and corticosterone (into cortisone and 11-dehydrocorticosterone, respectively).^[6]^[7] Inhibition of 11β-HSD2 by fluoxymesterone may result in mineralocorticoid receptor overactivation and associated side effects such as hypertension and fluid retention, and has been hypothesized to be involved in the cardiovascular and other adverse effects of fluoxymesterone.^[6]^[7]

Glucocorticoid activity

Unlike other AAS, fluoxymesterone has structural features in common with corticosteroids, including its 9α-fluoro and 11β-hydroxy groups.^[8] In accordance, it has weak (micromolar) but potentially clinically significant affinity for the glucocorticoid receptor.^[9]

Chemistry

Fluoxymesterone is an androstane steroid and a 17α-alkylated derivative of testosterone and is also known as 9α-fluoro-11β-hydroxy-17α-methyltestosterone or as 9α-fluoro-11β-hydroxy-17α-methylandrost-4-en-17β-ol-3-one.^[1]^[2]

Synthesis

Step One: The first step in the synthesis of fluoxymesterone is the microbiological oxidation of commercially available androstenedione (1.11) by Actinomyces; this introduces a hydroxyl group to the 11α-position (1.12), which is then oxidised to a ketone using Jones’ reagent, yielding the 3,11,17-triketone, adrenosterone (1.13). Pyrrolidine then reacts to form an enamine (1.14) by reaction with the 3α-keto group, protecting it from alkylation in a subsequent step. The regioselectivity of pyrrolidine for reaction at the 3α-position occurs inherently in the structure of adrenosterone, due to the position of the sterically bulky methyl groups. In subsequent steps, alkylation of the 17-keto group (1.14) using Grignard reagent, addition of hydride at the 11-position (1.15) and regeneration of the protected 3-keto group yields the starting material (1.16) for the final steps of the fluoxymesterone synthesis. This involves more standard synthetic transformations.

Scheme showing the full synthesis of fluoxymesterone from andrestenedione

StepTwo: The 11α-hydroxyl of the starting material (1.16) is sulfonylated by p-toluenesulfonyl chloride; addition of trimethylamine (base) deprotonates the 11α-carbon, yielding an (E₂) elimination of tosylate (pk_a - 5) to give olefin (1.17). Stereospecificity of reaction between olefin and hypobromous acid (HOBr) in base, N-bromosuccinimide (NBS), is determined by the formation of a bromonium intermediate; the electrophilic bromonium cation approaches the ring’s less sterically hindered α-face and is attacked by the π-electron density of the alkene. The hydroxide ion then attacks from above the ring (β-face) at the 11-carbon, resulting in a structure (1.18) by the stereospecific addition of hydroxyl and bromine across the double bond. Addition of sodium hydroxide results in deprotonation of the 11α-hydroxyl, and the subsequent structure undergoes an intramolecular S_N2 epoxy ring formation. The epoxy ring of the β-epoxide (1.19) is protonated to give an oxironium ion intermediate. In a concerted process, fluoride attacks the ring’s α-face from below, as one of the two oxygen-carbon bonds is broken on the opposite face; hence regenerating the 11α-hydroxyl trans to the fluorine substituent. The resulting structure (1.20) is the androgenic steroid, fluoxymesterone.

Detection in body fluids

Detection of halotestin and other such illegal anabolic steroids in sports is achieved by GS-MS identification of urinary excreted anabolic steroids and their metabolites. In a test for halotestin, a dry residue obtained from a urine sample is dissolved in dimethylformamide and a sulfur trioxide-pyridine complex and is heated with 1% potassium carbonate solution. Halotestin and many of its metabolites contain two polar hydroxyl groups, leading to intermolecular hydrogen bonding that increases their boiling point and reduces volatility. In order to attain a gaseous sample for GC-MS, the products of hydrolysis are extracted, dissolved in methanol and derivatised to form volatile trimethylsilyl (TMS) esters by adding N-methyl-N-trimethylsilyl-trifluoroacetamide (MSTFA) and trimethylsilylimidazole (TMSImi).^[10]

Society and culture

Brand names

Brand names of fluoxymesterone include Android-F, Halotestin, Ora-Testryl, and Ultandren, among others.^[1]^[2]^[3]

Availability

United States

Fluoxymesterone is one of the few AAS that remains available in the United States.^[11] The others (as of December 2016) are testosterone (and esters), methyltestosterone, nandrolone decanoate, oxandrolone, and oxymetholone.^[11]

References

^ ^a ^b ^c J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 568–. ISBN 978-1-4757-2085-3.
^ ^a ^b ^c Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. p. 461. ISBN 978-3-88763-075-1.
^ ^a ^b I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 123–. ISBN 978-94-011-4439-1.
^ Seth Roberts (2009). Anabolic Pharmacology.
^ Dr. K.V. Sastry (2008). Endocrinology and Reproductive Biology. Page 150. ISBN 81-7133-777-5.
^ ^a ^b ^c ^d Fürstenberger C, Vuorinen A, Da Cunha T, Kratschmar DV, Saugy M, Schuster D, Odermatt A (2012). "The anabolic androgenic steroid fluoxymesterone inhibits 11β-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation". Toxicol. Sci. 126 (2): 353–61. doi:10.1093/toxsci/kfs022. PMID 22273746.
^ ^a ^b ^c Joseph JF, Parr MK (2015). "Synthetic androgens as designer supplements". Curr Neuropharmacol. 13 (1): 89–100. doi:10.2174/1570159X13666141210224756. PMC 4462045. PMID 26074745.
^ Kirschbaum J (27 October 1978). Profiles of Drug Substances, Excipients and Related Methodology. Academic Press. pp. 253–. ISBN 978-0-08-086102-9.
^ Mayer M, Rosen F (1975). "Interaction of anabolic steroids with glucocorticoid receptor sites in rat muscle cytosol". Am. J. Physiol. 229 (5): 1381–6. PMID 173192.
^ Schänzer, Willi; Opfermann, Georg; Donike, Manfred (1992-11-01). "17-Epimerization of 17α-methyl anabolic steroids in humans: metabolism and synthesis of 17α-hydroxy-17β-methyl steroids". Steroids. 57 (11): 537–550. doi:10.1016/0039-128X(92)90023-3.
^ ^a ^b "Drugs@FDA: FDA Approved Drug Products" (HTML). United States Food and Drug Administration. Retrieved 17 December 2016.

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 原発性骨髄線維症のマネージメント management of primary myelofibrosis
2. 癌における食欲不振および悪液質の薬理学的マネージメント pharmacologic management of cancer anorexia cachexia
3. 転移性ホルモン受容体陽性乳癌に対する治療アプローチ：内分泌療法 treatment approach to metastatic hormone receptor positive breast cancer endocrine therapy
4. 緩和ケア：悪液質と食欲不振の評価および管理 palliative care assessment and management of anorexia and cachexia
5. 小児および思春期における遺伝性再生不良性貧血 inherited aplastic anemia in children and adolescents

English Journal

Alopecia with endocrine therapies in patients with cancer.

Saggar V, Wu S, Dickler MN, Lacouture ME.Author information School of Medicine, New York University Langone Medical Center, New York, New York, USA;AbstractBACKGROUND: Whereas the frequency of alopecia to cytotoxic chemotherapies has been well described, the incidence of alopecia during endocrine therapies (i.e., anti-estrogens, aromatase inhibitors) has not been investigated. Endocrine agents are widely used in the treatment and prevention of many solid tumors, principally those of the breast and prostate. Adherence to these therapies is suboptimal, in part because of toxicities. We performed a systematic analysis of the literature to ascertain the incidence and risk for alopecia in patients receiving endocrine therapies.
The oncologist.Oncologist.2013;18(10):1126-34. doi: 10.1634/theoncologist.2013-0193. Epub 2013 Sep 13.
BACKGROUND: Whereas the frequency of alopecia to cytotoxic chemotherapies has been well described, the incidence of alopecia during endocrine therapies (i.e., anti-estrogens, aromatase inhibitors) has not been investigated. Endocrine agents are widely used in the treatment and prevention of many sol
PMID 24037977

Mass spectrometric identification and characterization of new fluoxymesterone metabolites in human urine by liquid chromatography time-of-flight tandem mass spectrometry.

Lu J, He G, Wang X, Xu Y, Wu Y, Dong Y, Liu X, He Z, Zhao J, Yuan H.Author information National Anti-Doping Laboratory, China Anti-Doping Agency, ChaoYang District, Beijing, PR China. lujianghai@chinada.cnAbstractIn this study fluoxymesterone urinary profiles were investigated by liquid chromatography quadrupole time-of-flight tandem mass spectrometry (LC-QTOFMS) with accurate mass measurement. Twelve metabolites including the parent drug were detected in two fluoxymesterone positive control urine samples. Three parameters were employed for evaluation of the accuracy of the chemical formulae in positive full scan experiment, which contained error between actual and calculated mass weights of prontonated and isotopic molecules together with abundance match between prontonated and isotopic molecules. The 13 analytes were determined with mass accuracy less than 1.1 ppm and isotopic abundance match more than 94 marks. Based on the ionization, CID fragmentation, the accurate mass of the product ion and comparison of the accurate mass weight and retention time with reference standard, fluoxymesterone and its 12 metabolites containing three unreported ones were detected. The chemical structures of three unreported metabolites were identified as: 9-fluro-17β-ol-17-methyl-11-en-5α-androstan-3-one (F13), 9-fluro-17β-ol-17-methyl-11-en-5β-androstan-3-one (F8) and 9-fluro-17β-ol-17-methyl-5-androstan-3,6,11-trione, and meanwhile a dihydroxylated metabolite (F12), 6,16-dihydroxylated fluoxymesterone, was also detected in human urine, which was previously reported to be available only in equine urine.
Steroids.Steroids.2012 Jul;77(8-9):871-7. doi: 10.1016/j.steroids.2012.04.003. Epub 2012 Apr 13.
In this study fluoxymesterone urinary profiles were investigated by liquid chromatography quadrupole time-of-flight tandem mass spectrometry (LC-QTOFMS) with accurate mass measurement. Twelve metabolites including the parent drug were detected in two fluoxymesterone positive control urine samples. T
PMID 22521423

[Determination of 11 anabolic hormones in fish tissue by multi-function impurity adsorption solid-phase extraction-ultrafast liquid chromatography-tandem mass spectrometry].

Yao S, Zhao Y, Li X, Chen X, Jin M.Author information Ningbo Municipal Center for Disease Control and Prevention, Ningbo Key Laboratory of Poison Research and Control, Ningbo 315010, China. yaoss@nbcdc.org.cnAbstractA method was developed for the determination of 11 anabolic hormones (boldenone, androstenedione, nandrolone, methandrostenolone, methyltestosterone, testosterone, testosterone acetate, trenbolone, testosterone propionate, stanozolol, fluoxymesterone) in fish by multi-function impurity adsorption solid-phase extraction-ultrafast liquid chromatography-tandem mass spectrometry. After the sample was extracted by methanol, the extract was cleaned-up quickly by C18 adsorbent, neutral alumina adsorbent and amino-functionalized nano-adsorbent. The separation was performed on a Shim-Pack XR-ODS II column (100 mm x 2.0 mm, 2.2 microm) using the mobile phases of 0.1% (v/v) formic acid in acetonitrile and 0.1% (v/v) formic acid solution in a gradient elution mode. The identification and quantification were achieved by using electrospray ionization in positive ion mode (ESI+) in multiple reaction monitoring (MRM) mode. The matrix-matched external standard calibration curves were used for quantitative determination. The results showed that the calibration curves were in good linearity for the eleven analytes with the correlation coefficients (r) more than 0.999. The limits of detection (LODs, S/N > 3) for the 11 anabolic hormones were from 0.03 microg/kg to 0.4 microg/kg and the limits of quantification (LOQs, S/N > 10) were from 0.1 microg/kg to 1.5 microg/kg. The average recoveries ranged from 80.9% to 98.1% with the relative standard deviations between 5.2% and 11.5%. The method is simple, rapid, sensitive, accurate and suitable for the quantitative determination and confirmation of the 11 anabolic hormones in fish.
Se pu = Chinese journal of chromatography / Zhongguo hua xue hui.Se Pu.2012 Jun;30(6):572-7.
A method was developed for the determination of 11 anabolic hormones (boldenone, androstenedione, nandrolone, methandrostenolone, methyltestosterone, testosterone, testosterone acetate, trenbolone, testosterone propionate, stanozolol, fluoxymesterone) in fish by multi-function impurity adsorption so
PMID 23016290

Japanese Journal

Characterization and Quantification of Fluoxymesterone Metabolite in Horse Urine by Gas Chromatography/Mass Spectrometry

Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 24(7), 911-914, 2008-07-10
NAID 10025205192

Simultaneous Doping Analysis of Main Urinary Metabolites of Anabolic Steroids in Horse by Ion-trap Gas Chromatography-Tandem Mass Spectrometry

Analytical Sciences 24(9), 1199-1204, 2008
NAID 130004441730

Characterization and Quantification of Fluoxymesterone Metabolite in Horse Urine by Gas Chromatography/Mass Spectrometry

Analytical Sciences 24(7), 911-914, 2008
NAID 130004441681

Related Pictures

Fluoxymesterone / Halotestin profile > Fluoxymesterone - patient information, description, dosage and directions. Fluoxymesterone Genesis | Halotestin Tablets Fluoxymesterone(Halotestin) - Shenzhen RuiJin Pharmaceutical Co.,Ltd - ecplaza.net Halotestin La Pharma, oral anabolic steroid Halotestin (Fluoxymesterone) - Anabolic.org Halotestin - fluoxymesterone - steroizi.ro

★リンクテーブル★

リンク元	「フルオキシメステロン」

「フルオキシメステロン」

Fluoxymesterone
Clinical data
Trade names	Halotestin, Ora-Testryl, Ultandren, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682690
Pregnancy; category	X;
Routes of; administration	Oral
ATC code	G03BA01 (WHO)
Legal status
Legal status	CA: Schedule IV; US: Schedule III;
Pharmacokinetic data
Bioavailability	100% Oral
Metabolism	Hepatic
Biological half-life	9.5 hours
Excretion	urine
Identifiers
	IUPAC name 9-fluoro-11,17-dihydroxy-10,13,17-trimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one;
Synonyms	Androfluorene; NSC-12165; 9α-Fluoro-11β-hydroxy-17α-methyltestosterone
CAS Number	76-43-7
PubChem (CID)	6446
IUPHAR/BPS	2861
DrugBank	DB01185
ChemSpider	6205
UNII	9JU12S4YFY
KEGG	D00327
ChEBI	CHEBI:5120
ChEMBL	CHEMBL1445
ECHA InfoCard	100.000.875
Chemical and physical data
Formula	C20H29FO3
Molar mass	336.441 g/mol
3D model (Jmol)	Interactive image
	SMILES O=C4\C=C3/[C@]([C@@]2(F)[C@@H](O)C[C@]1([C@@H](CC[C@@]1(O)C)[C@@H]2CC3)C)(C)CC4 ;
	InChI InChI=1S/C20H29FO3/c1-17-8-6-13(22)10-12(17)4-5-15-14-7-9-19(3,24)18(14,2)11-16(23)20(15,17)21/h10,14-16,23-24H,4-9,11H2,1-3H3/t14-,15-,16-,17-,18-,19-,20-/m0/s1 ; Key:YLRFCQOZQXIBAB-RBZZARIASA-N ;
(verify)

　　[★]

英: fluoxymesterone
商: ハロテスチン

[Elks2014-1] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 568–. ISBN 978-1-4757-2085-3.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. p. 461. ISBN 978-3-88763-075-1.

[MortonHall2012-3] I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 123–. ISBN 978-94-011-4439-1.

[4] Seth Roberts (2009). Anabolic Pharmacology.

[5] Dr. K.V. Sastry (2008). Endocrinology and Reproductive Biology. Page 150. ISBN 81-7133-777-5.

[pmid22273746-6] Fürstenberger C, Vuorinen A, Da Cunha T, Kratschmar DV, Saugy M, Schuster D, Odermatt A (2012). "The anabolic androgenic steroid fluoxymesterone inhibits 11β-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation". Toxicol. Sci. 126 (2): 353–61. doi:10.1093/toxsci/kfs022. PMID 22273746.

[pmid26074745-7] Joseph JF, Parr MK (2015). "Synthetic androgens as designer supplements". Curr Neuropharmacol. 13 (1): 89–100. doi:10.2174/1570159X13666141210224756. PMC 4462045. PMID 26074745.

[Kirschbaum1978-8] Kirschbaum J (27 October 1978). Profiles of Drug Substances, Excipients and Related Methodology. Academic Press. pp. 253–. ISBN 978-0-08-086102-9.

[pmid173192-9] Mayer M, Rosen F (1975). "Interaction of anabolic steroids with glucocorticoid receptor sites in rat muscle cytosol". Am. J. Physiol. 229 (5): 1381–6. PMID 173192.

[10] Schänzer, Willi; Opfermann, Georg; Donike, Manfred (1992-11-01). "17-Epimerization of 17α-methyl anabolic steroids in humans: metabolism and synthesis of 17α-hydroxy-17β-methyl steroids". Steroids. 57 (11): 537–550. doi:10.1016/0039-128X(92)90023-3.

[Drugs.40FDA-11] "Drugs@FDA: FDA Approved Drug Products" (HTML). United States Food and Drug Administration. Retrieved 17 December 2016.

v t e Steroid hormone metabolism modulators

HMGCR	Inhibitors: Atorvastatin Cerivastatin Fluvastatin Lovastatin Mevastatin Pitavastatin Pravastatin Rosuvastatin Simvastatin

FPS	Inhibitors: Alendronic acid Clodronic acid Etidronic acid Ibandronic acid Incadronic acid Pamidronic acid Risedronic acid Tiludronic acid Zoledronic acid

24-DHCR24	20,25-Diazacholesterol Clomifene Triparanol

20,22-Desmolase (P450scc)	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 Δ⁴-Abiraterone Abiraterone Abiraterone acetate Amphenone Bifluranol Bifonazole Canrenone CFG-920 Clotrimazole Cyanoketone Cyproterone acetate Danazol Econazole Flutamide Galeterone Gestrinone Isoconazole Ketoconazole L-39 Levoketoconazole Liarozole LY-207,320 MDL-27,302 Miconazole Mifepristone Nilutamide Orteronel Pioglitazone Prochloraz Rosiglitazone Seviteronel Spironolactone Stanozolol SU-9055 SU-10603 TGF-β Tioconazole Troglitazone VN/87-1 YM116

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

3β-HSD	Inhibitors: 4-MA Δ⁴-Abiraterone Abiraterone Abiraterone acetate Azastene Cyanoketone Cyproterone acetate Danazol Epostane Genistein Gestrinone Medrogestone Medroxyprogesterone acetate Metyrapone Norethisterone Oxymetholone Pioglitazone Rosiglitazone Trilostane Troglitazone

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

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

11β-Hydroxylase	Inhibitors: Δ⁴-Abiraterone Abiraterone Abiraterone acetate Aminoglutethimide Canrenone Etomidate Fadrozole FETO Ketoconazole Levoketoconazole Metomidate Metyrapol Metyrapone Mitotane Potassium canrenoate Spironolactone Trilostane

18-Hydroxylase	Inhibitors: 18-Ethynylprogesterone (18-ethinylprogesterone) 18-Vinylprogesterone Aminoglutethimide Canrenone FAD286 Fadrozole Ketoconazole LCI699 Metyrapone Mespirenone Potassium canrenoate Spironolactone

17β-HSD	Inhibitors: Danazol Simvastatin

5α-Reductase	Inhibitors: 22-Oxime Δ⁴-Abiraterone Abiraterone Abiraterone acetate 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 Gestodene Izonsteride L-39 Lapisteride Oxendolone Saw palmetto TFM-4AS-1 Turosteride Vitamin B6 Zinc

Aromatase	Inhibitors: 4-AT 4-Cyclohexylaniline 4'-Hydroxynorendoxifen 4-Hydroxytestosterone 5α-DHNET 20α-Dihydroprogesterone Abyssinone II Aminoglutethimide Anastrozole Ascorbic acid (vitamin C) Atamestane ATD Bifonazole CGP-45,688 CGS-47,645 Chalconoids (e.g., isoliquiritigenin) Clotrimazole Corynesidone A Coumestrol 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)

SST/EST	4′OH-CB79 6-Hydroxyflavone 2,6-Dichloro-4-nitrophenol (DCNP) Equol Galangin Genistein Parabens (e.g., butylparaben) Pentachlorophenol (PCP) Triclosan

STS	AHBS Danazol Estrone-3-O-sulfamate (EMATE) Irosustat (STX64, 667 Coumate, BN-83495) KW-2581 SR-16157 STX213 STX681 STX1938

27-Hydroxylase	Inhibitors: Anastrozole Bicalutamide Dexmedetomidine Fadrozole Posaconazole Ravuconazole

Others	Inhibitors: Inhibit estradiol degradation: Cimetidine

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

匿名

検索

案内

案内

fluoxymesterone