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| {{Drugbox | | {{Short description|Overview of the drug Bifluranol}} |
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| | IUPAC_name = 2-Fluoro-4-[3-(3-fluoro-4-hydroxyphenyl)pentan-2-yl]phenol
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| | image = Bifluranol.svg
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| | width = 250px
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| <!--Clinical data-->
| | '''Bifluranol''' is a [[nonsteroidal antiandrogen]] (NSAA) that was developed for the treatment of [[prostate cancer]]. It is a member of the [[flutamide]] family of drugs, which are known for their ability to block the effects of [[androgens]] like [[testosterone]] in the body. |
| | tradename = Prostarex
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| | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| | pregnancy_US = <!-- A / B / C / D / X -->
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| | pregnancy_category =
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| | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
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| | legal_CA =
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| | legal_UK =
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| | legal_US =
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| | legal_status =
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| | routes_of_administration =
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| | class = [[Nonsteroidal estrogen]]
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| <!--Pharmacokinetic data-->
| | ==Mechanism of Action== |
| | bioavailability =
| | Bifluranol works by inhibiting the action of androgens at the [[androgen receptor]]s. Androgens are male sex hormones that play a key role in the development and maintenance of male characteristics. In conditions like prostate cancer, androgens can promote the growth of cancer cells. By blocking these hormones, Bifluranol helps to slow down or stop the growth of cancer cells. |
| | protein_bound =
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| | metabolism =
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| <!--Identifiers-->
| | ==Chemical Structure== |
| | CAS_number_Ref =
| | Bifluranol is chemically related to other nonsteroidal antiandrogens. Its structure allows it to bind to androgen receptors, preventing natural androgens from exerting their effects. This binding is competitive, meaning Bifluranol competes with natural androgens for receptor sites. |
| | CAS_number = 34633-34-6
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| | CAS_supplemental =
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| | ATC_prefix =
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| | ATC_suffix =
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| | PubChem = 71713
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| | DrugBank_Ref =
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| | DrugBank =
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| | ChemSpiderID_Ref =
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| | ChemSpiderID = 64763
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| | ChEMBL = 2105524
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| | UNII = 47602X79JF
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| | synonyms = BX-341
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| <!--Chemical data-->
| | ==Uses== |
| | C=17 | H=18 | F=2 | O=2
| | Bifluranol is primarily used in the treatment of [[prostate cancer]]. It may be used alone or in combination with other treatments such as [[surgery]], [[radiation therapy]], or other [[hormonal therapies]]. |
| | molecular_weight = 292.320 g/mol
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| | SMILES = CCC(C1=CC(=C(C=C1)O)F)C(C)C2=CC(=C(C=C2)O)F
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| | StdInChI_Ref =
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| | 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
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| | StdInChIKey_Ref =
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| | StdInChIKey = RDVXUHOSYIBGBT-UHFFFAOYSA-N
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| }}
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| '''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|author=J. Elks|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 | first1=J.B. | last1=Dekanski | title=Anti-prostatic activity of bifluranol, a fluorinated bibenzyl. | journal=British Journal of Pharmacology | year=1980 | volume=71 | issue=1 | pages=11–16 | issn=0007-1188 | doi=10.1111/j.1476-5381.1980.tb10903.x | pmid=6258683 |pmc=2044395 }}</ref><ref name="PopeGilbert1981">{{cite journal | first1=D. J. | last1=Pope | title=Bifluranol, a novel fluorinated bibenzyl anti-androgen, its chemistry and disposition in different animal species | last2=Gilbert | first2=A. P. | last3=Easter | first3=D. J. | last4=Chan | first4=R. P. | last5=Turner | first5=J. C. | last6=Gottfried | first6=S. | last7=Parke | first7=D. V. | journal=Journal of Pharmacy and Pharmacology | year=1981 | volume=33 | issue=1 | pages=297–301 | issn=0022-3573 | doi=10.1111/j.2042-7158.1981.tb13784.x | pmid=6116777}}</ref><ref name="BeacockBuck1985">{{cite journal|last1=Beacock|first1=C. J. M.|last2=Buck|first2=A. C.|last3=Roberts|first3=E. E.|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}}</ref><ref name="KeaneTimoney1988">{{cite journal | first1=P. F. | last1=Keane | title=Response of the Benign Hypertrophied Prostate to Treatment with an LHRH Analogue | last2=Timoney | first2=A. G. | last3=Kiely | first3=E. | last4=Williams | first4=Gordon | last5=Stamp | first5=G. | journal=British Journal of Urology | year=1988 | volume=62 | issue=2 | pages=163–165 | issn=0007-1331 | doi=10.1111/j.1464-410X.1988.tb04299.x | pmid=2457404}}</ref> It is a poly[[fluorine|fluorinated]] [[biphenyl]] that is related to [[polybrominated biphenyl|polybrominated]] and [[polychlorinated biphenyl]]s and [[diethylstilbestrol]].<ref name="PopeGilbert1981" /><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|author=M. K. Agarwal|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>
| | ==Side Effects== |
| | As with other antiandrogens, Bifluranol can cause a range of side effects. Common side effects include: |
| | * [[Gynecomastia]] (enlargement of breast tissue in men) |
| | * [[Hot flashes]] |
| | * [[Decreased libido]] |
| | * [[Fatigue]] |
| | * [[Nausea]] |
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| 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 | first1=S.E. | last1=Barrie | title=Inhibition of 17α-hydroxylase/C17-C20 lyase by bifluranol and its analogues | last2=Rowlands | first2=M.G. | last3=Foster | first3=A.B. | last4=Jarman | first4=M. | journal=Journal of Steroid Biochemistry | year=1989 | volume=33 | issue=6 | pages=1191–1195 | issn=0022-4731 | doi=10.1016/0022-4731(89)90429-9 | pmid=2559252}}</ref><ref name="JarmanJohn Smith1998">{{cite journal | first1=Michael | last1=Jarman | title=Inhibitors of enzymes of androgen biosynthesis: cytochrome P450<sub>17α</sub> and 5α-steroid reductase | last2=John Smith | first2=H. | last3=J. Nicholls | first3=Paul | last4=Simons | first4=Claire | journal=Natural Product Reports | year=1998 | volume=15 | issue=5 | pages=495 | issn=0265-0568 | doi=10.1039/a815495y}}</ref><ref name="BarrieHaynes1997">{{cite journal | first1=S.E. | last1=Barrie | title=Biochemistry and pharmacokinetics of potent non-steroidal cytochrome P450<sub>17α</sub> inhibitors | last2=Haynes | first2=B.P. | last3=Potter | first3=G.A. | last4=Chan | first4=F.C.Y. | last5=Goddard | first5=P.M. | last6=Dowsett | first6=M. | last7=Jarman | first7=M. | journal=The Journal of Steroid Biochemistry and Molecular Biology | year=1997 | volume=60 | issue=5-6 | pages=347–351 | issn=0960-0760 | doi=10.1016/S0960-0760(96)00225-7}}</ref>
| | ==Pharmacokinetics== |
| | The pharmacokinetics of Bifluranol involve its absorption, distribution, metabolism, and excretion. It is typically administered orally and is absorbed through the gastrointestinal tract. The drug is metabolized in the liver and excreted primarily through the urine. |
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| Related drugs include [[pentafluranol]] (BX-430) and [[terfluranol]] (BX-428), which are also estrogens.<ref name="Polonii1984">{{cite book|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> | | ==Related Pages== |
| | * [[Prostate cancer]] |
| | * [[Androgen receptor]] |
| | * [[Nonsteroidal antiandrogen]] |
| | * [[Flutamide]] |
| | * [[Hormonal therapy (oncology)]] |
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| ==See also==
| | [[Category:Nonsteroidal antiandrogens]] |
| * [[Acefluranol]]
| | [[Category:Prostate cancer treatments]] |
| * [[Paroxypropione]]
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| * [[Metallibure]]
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| ==References==
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| {{Reflist|30em}}
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| {{Estrogens and antiestrogens}}
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| {{Androgens and antiandrogens}}
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| {{Estrogen receptor modulators}}
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| [[Category:Abandoned drugs]] | |
| [[Category:Antigonadotropins]] | |
| [[Category:CYP17A1 inhibitors]]
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| [[Category:Enzyme inhibitors]]
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| [[Category:Fluoroarenes]]
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| [[Category:Synthetic estrogens]]
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| {{antineoplastic-drug-stub}}
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| {{genito-urinary-drug-stub}}
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| {{dictionary-stub1}}
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| <gallery>
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| File:Bifluranol.svg|Bifluranol
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| </gallery>
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Bifluranol is a nonsteroidal antiandrogen (NSAA) that was developed for the treatment of prostate cancer. It is a member of the flutamide family of drugs, which are known for their ability to block the effects of androgens like testosterone in the body.
Mechanism of Action[edit]
Bifluranol works by inhibiting the action of androgens at the androgen receptors. Androgens are male sex hormones that play a key role in the development and maintenance of male characteristics. In conditions like prostate cancer, androgens can promote the growth of cancer cells. By blocking these hormones, Bifluranol helps to slow down or stop the growth of cancer cells.
Chemical Structure[edit]
Bifluranol is chemically related to other nonsteroidal antiandrogens. Its structure allows it to bind to androgen receptors, preventing natural androgens from exerting their effects. This binding is competitive, meaning Bifluranol competes with natural androgens for receptor sites.
Bifluranol is primarily used in the treatment of prostate cancer. It may be used alone or in combination with other treatments such as surgery, radiation therapy, or other hormonal therapies.
Side Effects[edit]
As with other antiandrogens, Bifluranol can cause a range of side effects. Common side effects include:
Pharmacokinetics[edit]
The pharmacokinetics of Bifluranol involve its absorption, distribution, metabolism, and excretion. It is typically administered orally and is absorbed through the gastrointestinal tract. The drug is metabolized in the liver and excreted primarily through the urine.
Related Pages[edit]
