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Bifluranol

April 15, 2024

Bifluranol (INNTooltip International Nonproprietary Name, BANTooltip British Approved Name; 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][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
  • 2-Fluoro-4-[3-(3-fluoro-4-hydroxyphenyl)pentan-2-yl]phenol
CAS Number
  • 34633-34-6
PubChem CID
  • 71713
ChemSpider
  • 64763
UNII
  • 47602X79JF
ChEBI
  • CHEBI:135219
ChEMBL
  • ChEMBL2105524
Chemical and physical data
FormulaC17H18F2O2
Molar mass292.326 g·mol−1
3D model (JSmol)
  • Interactive image
  • CCC(C1=CC(=C(C=C1)O)F)C(C)C2=CC(=C(C=C2)O)F
  • 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 edit

References edit

  1. ^ Elks J (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. ^ a b c d Dekanski JB (1980). "Anti-prostatic activity of bifluranol, a fluorinated bibenzyl". British Journal of Pharmacology. 71 (1): 11–16. 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 CJ, Buck AC, Roberts EE (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): 163–165. doi:10.1111/j.1464-410X.1988.tb04299.x. PMID 2457404.
  7. ^ a b 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): 1191–1195. 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): 347–351. 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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April 15, 2024
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Bifluranol INNTooltip International Nonproprietary Name BANTooltip British Approved Name 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 7 8 The drug is described as a weak estrogen and possesses about one eighth the potency of diethylstilbestrol 3 7 9 BifluranolClinical dataTrade namesProstarexOther namesBX 341Drug classNonsteroidal estrogenIdentifiersIUPAC name 2 Fluoro 4 3 3 fluoro 4 hydroxyphenyl pentan 2 yl phenolCAS Number34633 34 6PubChem CID71713ChemSpider64763UNII47602X79JFChEBICHEBI 135219ChEMBLChEMBL2105524Chemical and physical dataFormulaC 17H 18F 2O 2Molar mass292 326 g mol 13D model JSmol Interactive imageSMILES CCC C1 CC C C C1 O F C C C2 CC C C C2 O FInChI 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 2H3Key RDVXUHOSYIBGBT UHFFFAOYSA NIn 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 17a 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 editAcefluranol Paroxypropione MetallibureReferences edit Elks J 14 November 2014 The Dictionary of Drugs Chemical Data Chemical Data Structures and Bibliographies Springer p 152 ISBN 978 1 4757 2085 3 Index Nominum 2000 International Drug Directory Taylor amp Francis January 2000 pp 124 ISBN 978 3 88763 075 1 a b c d Dekanski JB 1980 Anti prostatic activity of bifluranol a fluorinated bibenzyl British Journal of Pharmacology 71 1 11 16 doi 10 1111 j 1476 5381 1980 tb10903 x PMC 2044395 PMID 6258683 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 Beacock CJ Buck AC Roberts EE 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 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 2 163 165 doi 10 1111 j 1464 410X 1988 tb04299 x PMID 2457404 a b Spain Ministerio de Agricultura Universidad Complutense de Madrid Departamento de Genetico y Mejora 1978 3rd World Congress of Animal Feeding Industrias Graficas Espana p 532 ISBN 978 84 7391 022 4 Annual Reports in Medicinal Chemistry Academic Press 16 September 1986 pp 182 ISBN 978 0 08 058365 5 Agarwal MK 1987 Receptor mediated antisteroid action De Gruyter p 330 ISBN 978 0 89925 374 9 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 1195 doi 10 1016 0022 4731 89 90429 9 PMID 2559252 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 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 6 347 351 doi 10 1016 S0960 0760 96 00225 7 PMID 9219927 S2CID 54340023 Polska Akademia Nauk Komitet Badania Polonii 1984 Kubiak H Wrobel J eds II Kongres Uczonych Polskiego Pochodzenia zbior materialow Zaklad Narodowy im Ossolinskich 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 nbsp This antineoplastic or immunomodulatory drug article is a stub You can help Wikipedia by expanding it vte nbsp This drug article relating to the genito urinary system is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Bifluranol amp oldid 1190647968, wikipedia, wiki, book, books, library,

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