Bifluranol

Bifluranol
INN
Drug class	Nonsteroidal estrogen
Routes of administration
Pregnancy category
Bioavailability
Metabolism
Elimination half-life
Excretion
Legal status
CAS Number	34633-34-6
PubChem	71713
DrugBank
ChemSpider	64763
KEGG

Bifluranol (INN , BAN

brand name Prostarex; former developmental code name BX-341) is a 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">{{{last}}},

 J. Elks, 
  
 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. online version, 
  
 Springer, 
  
  
  
 ISBN 978-1-4757-2085-3, 
  
  
  
 Pages: 152,</ref><ref name="IndexNominum2000">, 
  
 Index Nominum 2000: International Drug Directory. online version, 
  
 Taylor & Francis, 
  
  
  
 ISBN 978-3-88763-075-1, 
  
  
  
 Pages: 124–,</ref><ref name="Dekanski1980">, 
 Anti-prostatic activity of bifluranol, a fluorinated bibenzyl., 
 British Journal of Pharmacology, 
 1980,
 Vol. 71(Issue: 1),
 pp. 11–16,
 DOI: 10.1111/j.1476-5381.1980.tb10903.x,
 PMID: 6258683,
 PMC: 2044395,</ref><ref name="PopeGilbert1981">, 
 Bifluranol, a novel fluorinated bibenzyl anti-androgen, its chemistry and disposition in different animal species, 
 Journal of Pharmacy and Pharmacology, 
 1981,
 Vol. 33(Issue: 1),
 pp. 297–301,
 DOI: 10.1111/j.2042-7158.1981.tb13784.x,
 PMID: 6116777,</ref><ref name="BeacockBuck1985">, 
 Bifluranol in the treatment of benign prostatic hyperplasia (BPH), 
 The Prostate, 
 1985,
 Vol. 7(Issue: 4),
 pp. 357–361,
 DOI: 10.1002/pros.2990070403,</ref><ref name="KeaneTimoney1988">, 
 Response of the Benign Hypertrophied Prostate to Treatment with an LHRH Analogue, 
 British Journal of Urology, 
 1988,
 Vol. 62(Issue: 2),
 pp. 163–165,
 DOI: 10.1111/j.1464-410X.1988.tb04299.x,
 PMID: 2457404,</ref> It is a polyfluorinated biphenyl that is related to polybrominated and polychlorinated biphenyls and diethylstilbestrol.<ref name="PopeGilbert1981" /><ref name="AgriculturaMejora1978">, 
  
 3rd World Congress of Animal Feeding. online version, 
  
 Industrias Gráficas España, 
 1978, 
  
  
 ISBN 978-84-7391-022-4,</ref><ref name="AcademicPress1986">, 
  
 Annual Reports in Medicinal Chemistry. online version, 
  
 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">{{{last}}}, 
 M. K. Agarwal, 
  
 Receptor mediated antisteroid action. online version, 
  
 De Gruyter, 
 1987, 
  
  
 ISBN 978-0-89925-374-9,</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 antagonize the action of androgens.<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 gonadal androgen production and systemic androgen levels.<ref name="Dekanski1980" /> Bifluranol has also been found to act as a 17α-hydroxylase/17,20 lyase inhibitor, though with less 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">,

 Inhibition of 17α-hydroxylase/C17-C20 lyase by bifluranol and its analogues, 
 Journal of Steroid Biochemistry, 
 1989,
 Vol. 33(Issue: 6),
 pp. 1191–1195,
 DOI: 10.1016/0022-4731(89)90429-9,
 PMID: 2559252,</ref><ref name="JarmanJohn Smith1998">, 
 Inhibitors of enzymes of androgen biosynthesis: cytochrome P45017α and 5α-steroid reductase, 
 Natural Product Reports, 
 1998,
 Vol. 15(Issue: 5),
 pp. 495,
 DOI: 10.1039/a815495y,</ref><ref name="BarrieHaynes1997">, 
 Biochemistry and pharmacokinetics of potent non-steroidal cytochrome P45017α inhibitors, 
 The Journal of Steroid Biochemistry and Molecular Biology, 
 1997,
 Vol. 60(Issue: 5-6),
 pp. 347–351,
 DOI: 10.1016/S0960-0760(96)00225-7,</ref>

Related drugs include pentafluranol (BX-430) and terfluranol (BX-428), which are also estrogens.<ref name="Polonii1984">{{{last}}},

 Polska Akademia Nauk. Komitet Badania Polonii, 
  
 II Kongres Uczonych Polskiego Pochodzenia: zbiór materiałów. online version, 
  
 Zakład Narodowy im. Ossolińskich, 
 1984, 
  
  
 ISBN 978-83-04-01670-5,</ref>

See also

• Acefluranol
• Paroxypropione
• Metallibure

References

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