Bifluranol

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.[1][2][3][4][5][6] It is a polyfluorinated biphenyl that is related to polybrominated and polychlorinated biphenyls and diethylstilbestrol.[4][7][8] The drug is described as a weak estrogen, and possesses about one-eighth the potency of diethylstilbestrol.[3][7][9]

Bifluranol
Clinical data
Trade namesProstarex
Other namesBX-341
Drug classNonsteroidal estrogen
Identifiers
IUPAC name
  • 2-Fluoro-4-[3-(3-fluoro-4-hydroxyphenyl)pentan-2-yl]phenol
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
Chemical and physical data
FormulaC17H18F2O2
Molar mass292.326 g·mol−1
3D model (JSmol)
SMILES
  • CCC(C1=CC(=C(C=C1)O)F)C(C)C2=CC(=C(C=C2)O)F
InChI
  • InChI=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
  • Key:RDVXUHOSYIBGBT-UHFFFAOYSA-N

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.[3] 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.[3] 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.[10][11][12]

Related drugs include pentafluranol (BX-430) and terfluranol (BX-428), which are also estrogens.[13]

See also

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 152. ISBN 978-1-4757-2085-3.
  2. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 124–. ISBN 978-3-88763-075-1.
  3. Dekanski JB (1980). "Anti-prostatic activity of bifluranol, a fluorinated bibenzyl". British Journal of Pharmacology. 71 (1): 11–6. doi:10.1111/j.1476-5381.1980.tb10903.x. PMC 2044395. PMID 6258683.
  4. Pope DJ, Gilbert AP, Easter DJ, Chan RP, Turner JC, Gottfried S, Parke DV (May 1981). "Bifluranol, a novel fluorinated bibenzyl anti-androgen, its chemistry and disposition in different animal species". The Journal of Pharmacy and Pharmacology. 33 (5): 297–301. doi:10.1111/j.2042-7158.1981.tb13784.x. PMID 6116777. S2CID 40258860.
  5. Beacock, C. J. M.; Buck, A. C.; Roberts, E. E. (1985). "Bifluranol in the treatment of benign prostatic hyperplasia (BPH)". The Prostate. 7 (4): 357–361. doi:10.1002/pros.2990070403. ISSN 0270-4137. S2CID 71645575.
  6. Keane PF, Timoney AG, Kiely E, Williams G, Stamp G (August 1988). "Response of the benign hypertrophied prostate to treatment with an LHRH analogue". British Journal of Urology. 62 (2): 163–5. doi:10.1111/j.1464-410X.1988.tb04299.x. PMID 2457404.
  7. Spain. Ministerio de Agricultura; Universidad Complutense de Madrid. Departamento de Genetico y Mejora (1978). 3rd World Congress of Animal Feeding. Industrias Gráficas España. p. 532. ISBN 978-84-7391-022-4.
  8. Annual Reports in Medicinal Chemistry. Academic Press. 16 September 1986. pp. 182–. ISBN 978-0-08-058365-5.
  9. Agarwal MK (1987). Receptor mediated antisteroid action. De Gruyter. p. 330. ISBN 978-0-89925-374-9.
  10. Barrie SE, Rowlands MG, Foster AB, Jarman M (December 1989). "Inhibition of 17 alpha-hydroxylase/C17-C20 lyase by bifluranol and its analogues". Journal of Steroid Biochemistry. 33 (6): 1191–5. doi:10.1016/0022-4731(89)90429-9. PMID 2559252.
  11. Jarman M, Smith HJ, Nicholls PJ, Simons C (October 1998). "Inhibitors of enzymes of androgen biosynthesis: cytochrome P450(17) alpha and 5 alpha-steroid reductase". Natural Product Reports. 15 (5): 495–512. doi:10.1039/a815495y. PMID 9807812.
  12. Barrie SE, Haynes BP, Potter GA, Chan FC, Goddard PM, Dowsett M, Jarman M (March 1997). "Biochemistry and pharmacokinetics of potent non-steroidal cytochrome P450(17alpha) inhibitors". The Journal of Steroid Biochemistry and Molecular Biology. 60 (5–6): 347–51. doi:10.1016/S0960-0760(96)00225-7. PMID 9219927. S2CID 54340023.
  13. Polska Akademia Nauk. Komitet Badania Polonii (1984). Kubiak H, Wróbel J (eds.). II Kongres Uczonych Polskiego Pochodzenia: zbiór materiałów. Zakład Narodowy im. Ossolińskich. ISBN 978-83-04-01670-5. [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 ...]
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