Bifluranol (formerly also known as BX-341; traded name Prostarex), a novel fluorinated bibenzyl anti-androgen, is a potent and synthetic nonsteroidal estrogen of the stilbestrol calss related to diethylstilbestrol that has been used as an antiandrogen in the United Kingdom in the treatment of benign prostatic hyperplasia. 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.
Physicochemical Properties
| Molecular Formula | C17H18O2F2 |
| Molecular Weight | 292.32042 |
| Exact Mass | 292.127 |
| CAS # | 34633-34-6 |
| PubChem CID | 12850912 |
| Appearance | White to off-white solid powder |
| Density | 1.221g/cm3 |
| Boiling Point | 361.6ºC at 760mmHg |
| Flash Point | 172.5ºC |
| Index of Refraction | 1.565 |
| LogP | 4.673 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 4 |
| Heavy Atom Count | 21 |
| Complexity | 326 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | CC[C@@H](C1=CC(=C(C=C1)O)F)[C@H](C)C2=CC(=C(C=C2)O)F |
| InChi Key | RDVXUHOSYIBGBT-ZWNOBZJWSA-N |
| InChi Code | 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/t10-,13-/m1/s1 |
| Chemical Name | Phenol, 4,4'-(1-ethyl-2-methyl-1,2-ethanediyl)bis(2-fluoro-, (R*,S*)- |
| Synonyms | BX-341; BX-341; BX-341; traded name Prostarex |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vivo | Diflunol's distribution, absorption, and excretion have all been studied in mice, rats, ferrets, and dogs. Although diflunol is easily absorbed when taken orally, its concentration in blood is lower because of hepatic absorption and bile excretion. Following an intravenous injection of [3H]difluorol in rats (200 μg/kg) and ferrets (60 μg/kg), there was a rapid decrease in 3H blood concentrations within the first two to three hours. In female mice, this decrease was more rapid (18 minutes). compared to males (rats 1.0 hours, ferrets 1.4 hours) (rats, 30 minutes). Following this, the concentration drops below 15 ng bisfluranol equivalent mL-1 (rat) or 1 ng bisfluranol equivalent mL-1 (ferret) after 96 hours, with the rate of decline being much slower (40 hours for rats and 20 hours for ferrets) [1]. |
| References |
[1]. Bifluranol, a novel fluorinated bibenzyl anti-androgen, its chemistry and disposition in different animal species. J Pharm Pharmacol. 1981 May;33(5):297-301. |
| Additional Infomation | (2S,3R)-bifluranol is a 4,4'-pentane-2,3-diylbis(2-fluorophenol) that has (2S,3R)-stereoconfiguration. It is an enantiomer of a (2R,3S)-bifluranol. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~342.09 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.55 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.55 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4209 mL | 17.1045 mL | 34.2091 mL | |
| 5 mM | 0.6842 mL | 3.4209 mL | 6.8418 mL | |
| 10 mM | 0.3421 mL | 1.7105 mL | 3.4209 mL |