Просмотр кода страницы Английская Википедия:Bifluranol

{{Английская Википедия/Панель перехода}}
{{Short description|Mixture of two compounds}}
{{Drugbox
| Verifiedfields = 
| Watchedfields = 
| verifiedrevid = 
| IUPAC_name = 2-Fluoro-4-[3-(3-fluoro-4-hydroxyphenyl)pentan-2-yl]phenol
| image = Bifluranol.svg
| width = 250px

<!--Clinical data-->
| tradename = Prostarex
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = 
| legal_UK = 
| legal_US = 
| legal_status = 
| routes_of_administration = 
| class = [[Nonsteroidal estrogen]]

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion = 

<!--Identifiers-->
| CAS_number_Ref = 
| CAS_number = 34633-34-6
| CAS_supplemental = 
| ATC_prefix = 
| ATC_suffix = 
| PubChem = 71713
| DrugBank_Ref = 
| DrugBank = 
| ChEBI = 135219
| ChemSpiderID_Ref = 
| ChemSpiderID = 64763
| ChEMBL = 2105524
| UNII = 47602X79JF
| synonyms = BX-341

<!--Chemical data-->
| C=17 | H=18 | F=2 | O=2
| SMILES = CCC(C1=CC(=C(C=C1)O)F)C(C)C2=CC(=C(C=C2)O)F
| StdInChI_Ref = 
| StdInChI = 1S/C17H18F2O2/c1-3-13(12-5-7-17(21)15(19)9-12)10(2)11-4-6-16(20)14(18)8-11/h4-10,13,20-21H,3H2,1-2H3
| StdInChIKey_Ref = 
| StdInChIKey = RDVXUHOSYIBGBT-UHFFFAOYSA-N
}}

'''Bifluranol''' ({{abbrlink|INN|International Nonproprietary Name}}, {{abbrlink|BAN|British Approved Name}}; brand name '''Prostarex'''; former developmental code name '''BX-341''') is a [[synthetic compound|synthetic]] [[nonsteroidal estrogen]] of the [[stilbestrol]] group related to [[diethylstilbestrol]] that has been used as an [[antiandrogen]] in the [[United Kingdom]] in the treatment of [[benign prostatic hyperplasia]].<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=RA1-PA364|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=152}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA124|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=124–}}</ref><ref name="Dekanski1980">{{cite journal | vauthors = Dekanski JB | title = Anti-prostatic activity of bifluranol, a fluorinated bibenzyl | journal = British Journal of Pharmacology | volume = 71 | issue = 1 | pages = 11–16 | year = 1980 | pmid = 6258683 | pmc = 2044395 | doi = 10.1111/j.1476-5381.1980.tb10903.x }}</ref><ref name="PopeGilbert1981">{{cite journal | vauthors = Pope DJ, Gilbert AP, Easter DJ, Chan RP, Turner JC, Gottfried S, Parke DV | title = Bifluranol, a novel fluorinated bibenzyl anti-androgen, its chemistry and disposition in different animal species | journal = The Journal of Pharmacy and Pharmacology | volume = 33 | issue = 5 | pages = 297–301 | date = May 1981 | pmid = 6116777 | doi = 10.1111/j.2042-7158.1981.tb13784.x | s2cid = 40258860 }}</ref><ref name="BeacockBuck1985">{{cite journal| vauthors = Beacock CJ, Buck AC, Roberts EE |title=Bifluranol in the treatment of benign prostatic hyperplasia (BPH)|journal=The Prostate|volume=7|issue=4|year=1985|pages=357–361|issn=0270-4137|doi=10.1002/pros.2990070403|s2cid=71645575}}</ref><ref name="KeaneTimoney1988">{{cite journal | vauthors = Keane PF, Timoney AG, Kiely E, Williams G, Stamp G | title = Response of the benign hypertrophied prostate to treatment with an LHRH analogue | journal = British Journal of Urology | volume = 62 | issue = 2 | pages = 163–165 | date = August 1988 | pmid = 2457404 | doi = 10.1111/j.1464-410X.1988.tb04299.x }}</ref><ref name="AgriculturaMejora1978">{{cite book|author1=Spain. Ministerio de Agricultura|author2=Universidad Complutense de Madrid. Departamento de Genetico y Mejora|title=3rd World Congress of Animal Feeding|url=https://books.google.com/books?id=ZgYFAQAAIAAJ|year=1978|publisher=Industrias Gráficas España|isbn=978-84-7391-022-4|page=532}}</ref><ref name="AcademicPress1986">{{cite book|title=Annual Reports in Medicinal Chemistry|url=https://books.google.com/books?id=qsFCGskRHZQC&pg=PA182|date=16 September 1986|publisher=Academic Press|isbn=978-0-08-058365-5|pages=182–}}</ref> The drug is described as a weak estrogen, and possesses about one-eighth the potency of diethylstilbestrol.<ref name="Dekanski1980" /><ref name="AgriculturaMejora1978" /><ref name="Agarwal1987">{{cite book| vauthors = Agarwal MK |title=Receptor mediated antisteroid action|url=https://books.google.com/books?id=JfNsAAAAMAAJ|year=1987|publisher=De Gruyter|isbn=978-0-89925-374-9|page=330}}</ref>

In spite of the fact that it is widely referred to as an antiandrogen in the literature, bifluranol is actually a pure estrogen and does not significantly bind to the [[androgen receptor]] or directly [[receptor antagonist|antagonize]] the action of [[androgen]]s.<ref name="Dekanski1980" /> It exerts functional antiandrogen effects by binding to and activating the [[estrogen receptor]] in the [[pituitary gland]], consequently suppressing the secretion of [[luteinizing hormone]] (and hence acting as an [[antigonadotropin]]) and thereby reducing [[gonad]]al androgen production and systemic androgen levels.<ref name="Dekanski1980" /> Bifluranol has also been found to act as a [[CYP17A1|17α-hydroxylase/17,20 lyase]] [[enzyme inhibitor|inhibitor]], though with less [[potency (pharmacology)|potency]] than [[ketoconazole]], and this action may contribute to its efficacy in benign prostatic hyperplasia by further helping to lower androgen levels.<ref name="BarrieRowlands1989">{{cite journal | vauthors = Barrie SE, Rowlands MG, Foster AB, Jarman M | title = Inhibition of 17 alpha-hydroxylase/C17-C20 lyase by bifluranol and its analogues | journal = Journal of Steroid Biochemistry | volume = 33 | issue = 6 | pages = 1191–1195 | date = December 1989 | pmid = 2559252 | doi = 10.1016/0022-4731(89)90429-9 }}</ref><ref name="JarmanJohn Smith1998">{{cite journal | vauthors = Jarman M, Smith HJ, Nicholls PJ, Simons C | title = Inhibitors of enzymes of androgen biosynthesis: cytochrome P450(17) alpha and 5 alpha-steroid reductase | journal = Natural Product Reports | volume = 15 | issue = 5 | pages = 495–512 | date = October 1998 | pmid = 9807812 | doi = 10.1039/a815495y }}</ref><ref name="BarrieHaynes1997">{{cite journal | vauthors = Barrie SE, Haynes BP, Potter GA, Chan FC, Goddard PM, Dowsett M, Jarman M | title = Biochemistry and pharmacokinetics of potent non-steroidal cytochrome P450(17alpha) inhibitors | journal = The Journal of Steroid Biochemistry and Molecular Biology | volume = 60 | issue = 5–6 | pages = 347–351 | date = March 1997 | pmid = 9219927 | doi = 10.1016/S0960-0760(96)00225-7 | s2cid = 54340023 }}</ref>

Related drugs include [[pentafluranol]] (BX-430) and [[terfluranol]] (BX-428), which are also estrogens.<ref name="Polonii1984">{{cite book | veditors = Kubiak H, Wróbel J | author = Polska Akademia Nauk. Komitet Badania Polonii|title=II Kongres Uczonych Polskiego Pochodzenia: zbiór materiałów|url=https://books.google.com/books?id=_-VjAAAAIAAJ|year=1984|publisher=Zakład Narodowy im. Ossolińskich|isbn=978-83-04-01670-5|quote=[This explains why the estrogenic activity is minimal in terms of pentafluranol or even bifluranol. Doses which shall apply from 1 to 6 days of pregnancy, are in micrograms per kg of body weight: bifluranol 80, 30 and terfluranol pentafluranol 280 ...]}}</ref>

== See also ==
* [[Acefluranol]]
* [[Paroxypropione]]
* [[Metallibure]]

== References ==
{{Reflist|30em}}

{{Estrogens and antiestrogens}}
{{Androgens and antiandrogens}}
{{Estrogen receptor modulators}}

[[Category:Abandoned drugs]]
[[Category:Antigonadotropins]]
[[Category:CYP17A1 inhibitors]]
[[Category:Enzyme inhibitors]]
[[Category:Fluoroarenes]]
[[Category:Synthetic estrogens]]

{{antineoplastic-drug-stub}}
{{genito-urinary-drug-stub}}
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