Bifluranol (BX341)
(Synonyms: BX341) 目录号 : GC31577
Bifluranol (BX341) (BX341) 是一种抗雄激素。
Cas No.:34633-34-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Animal experiment: | Mice, Rats, Dogs and Ferrets[1]Swiss albino mice (24-28 g, males age 4 weeks, females age 6 weeks; pregnant mice mated at 6 weeks, used at day 18 of pregnancy) and Wistar albino rats (200 g males age 6 weeks, females age 8 weeks; 350 g males age 10 weeks) are fed Dixon's mouse and rat diet and have free access to water. Albino ferrets (0.7-2.6 kg, age 9-15 months) are fed raw meat, bread and milk. Male beagles (10.8-12.3 kg, age 10-14 years) are fed Spratt's complete dog diet. [3H]Bifluranol administration is by intragastric intubation, in propylene glycol (mouse 0.1 ml, rat 0.1-0.2 mL, ferret 0.1-0.4 mL and dog 1 mL), except for the dog 96 h excretion study when the drug is absorbed onto starch and given in a gelatin capsule. Bifluranol is given intravenously in propylene glycol-0.9% NaCl (saline) (1 : 1 v/v) (0.1-0.2 mL), via a tail vein in mice and rats and the jugular vein in ferrets (under ether anaesthesia). [3H]Bifluranol (2 mg/kg, 1.1 mCi) is administered orally or intravenously to male, female and pregnant mice. After various time intervals they are killed under ether anaesthesia by immersion in solid CO2-hexane (-70°C). The tail, limbs and ears are removed. The animals shaved, embedded and frozen in 5 % aq. acacia wax. The animal blocks are cut using a Slee whole-body freezing microtome to obtain lateral sections (30 pm) which are exposed to X-ray film at 4°C and the auto-radiograms examined after 1,3 or 6 months. [3H]Bifluranol is adrninistered orally or intravenously to rats (200 μg/kg, 0.86-1.0 mCi) , ferrets (60 μg/kg, 5.0-10.6 mCi) and orally only to dogs (50 μg/kg, 70-76 mCi) . Blood samples (10-100 μL) are taken for radioactivity determination at time intervals up to 96 h (rat and ferret) or 6 h (dog). |
References: [1]. Pope DJ, et al. Bifluranol, a novel fluorinated bibenzyl anti-androgen, its chemistry and disposition in different animal species. J Pharm Pharmacol. 1981 May;33(5):297-301. | |
Bifluranol (BX341) is an anti-androgen.
The absorption, distribution and excretion of Bifluranol have been studied in mouse, rat, ferret and dog; Bifluranol is readily absorbed following oral administration, but blood concentrations of Bifluranol are low due to hepatic uptake and biliary excretion. After intravenous administration of [3H]Bifluranol to rats (200 μg/kg) and ferrets (60 μg/kg) the blood concentrations of 3H decreases rapidly for the first 2 to 3 h, with the decrease being more rapid in females ( 18 min for rat, 30 min for ferret) than males (1.0 h for rat, 1.4 h for ferret). This is followed by a much slower decline (40 h for rat, 20 h for ferret) to concentrations at 96 h of less than 15 ng Bifluranol equivalents mL-1 (rat) or 1 ng Bifluranol equivalents mL-1 (ferret)[1].
[1]. Pope DJ, et al. Bifluranol, a novel fluorinated bibenzyl anti-androgen, its chemistry and disposition in different animal species. J Pharm Pharmacol. 1981 May;33(5):297-301.
| Cas No. | 34633-34-6 | SDF | |
| 别名 | BX341 | ||
| Canonical SMILES | C[C@H](C1=CC(F)=C(O)C=C1)[C@H](C2=CC(F)=C(O)C=C2)CC | ||
| 分子式 | C17H18F2O2 | 分子量 | 292.32 |
| 溶解度 | Soluble in DMSO | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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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 |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
The metabolism of bifluranol by rat, dog and ferret
The synthesis of monohydroxy- and dihydroxy-bifluranol, and of glucuronide and sulphate conjugates of bifluranol are described. Bifluranol administered orally to rats, ferrets and dogs at a dosage of 50 to 200 microgram kg-1 is mostly excreted in the faeces as unchanged bifluranol and bifluranol monosulphate, disulphate and monoglucuronide. The bifluranol is well absorbed and is mostly excreted in the bile, as six different conjugates, including a glucuronide sulphate found in all 3 species, and a glucuronide phosphate found only in ferret and dog bile. Hydroxylation of the aromatic rings occurs in the rat, to an extent of about 8% of the dose, but was not detected in ferret or dog.
Anti-prostatic activity of bifluranol, a fluorinated bibenzyl
1 Endocrine and anti-fertility studies were carried out on a fluorinated bibenzyl, bifluranol, in rats and mice. 2 A potent anti-prostatic activity of bifluranol was shown to be comparable to diethylstilboestrol (DES). In contrast, its oestrogenic potency by the oral route was about eight times less than that of DES. 3 In comparative short and long-term anti-androgenic and fertility studies in rats and in studies on sexual potency and reproductive performance in male mice, bifluranol given orally was shown to produce fully reversible suppression of accessory sexual structures without impairment of spermatogenesis and fertility. In contrast, DES administered in the same dose reduced spermatogenesis as well as accessory sexual glands. 4 Bifluranol lowered serum luteinising hormone (LH) levels without affecting follicle stimulating hormone (FSH). Under similar conditions DES reduces both LH and FSH levels. Since bifluranol does not antagonize androgen-induced stimulation of the prostate in castrated rats, its anti-prostatic effect is interpreted as a negative, hormonostatic feedback activity, mediated through a selective inhibition of LH secretion.
Inhibition of 17 alpha-hydroxylase/C17-C20 lyase by bifluranol and its analogues
A simple assay for the measurement of the activities of both 17 alpha-hydroxylase and C17-C20 lyase is described. No extraction procedures are required. The separation of substrate and products is achieved using HPLC which allows the collection of the components of interest and the monitoring of the recovery of various steroids. Using this assay, bifluranol (known to show anti-prostatic activity in vivo) and some analogues were tested for inhibitory activity towards these enzyme activities. Each compound was active, although less potent than ketoconazole, and this activity may contribute towards the in vivo action.
Enantioselective installation of adjacent tertiary benzylic stereocentres using lithiation-borylation-protodeboronation methodology. Application to the synthesis of bifluranol and fluorohexestrol
1,2-Diaryl ethanes bearing 1,2-stereogenic centres show interesting biological activity but their stereocontrolled synthesis has not been reported forcing a reliance of methods involving diastereomer and enantiomer separation. We have found that this class of molecules can be prepared with very high stereocontrol using lithiation-borylation methodology. The reaction of an enantioenriched benzylic lithiated carbamate with an enantioenriched benzylic secondary pinacol boronic ester gave a tertiary boronic ester with complete diastereo- and enantiocontrol. It was essential to use MgBr2/MeOH after formation of the boronate complex, both to promote the 1,2-migration and to trap any lithiated carbamate/benzylic anion that formed from fragmentation of the ate complex, anions that would otherwise racemise and re-form the boronate complex eroding both er and dr of the product. When the benzylic lithiated carbamate and benzylic secondary pinacol boronic ester were too hindered, boronate complex did not even form. In these cases, it was found that the use of the less hindered neopentyl boronic esters enabled successful homologation to take place even for the most hindered reaction partners, with high stereocontrol and without the need for additives. Protodeboronation of the product boronic esters with TBAF gave the target 1,2-diaryl ethanes bearing 1,2-stereogenic centres. The methodology was applied to the stereocontrolled synthesis of bifluranol and fluorohexestrol in just 7 and 5 steps, respectively.
Bifluranol, a novel fluorinated bibenzyl anti-androgen, its chemistry and disposition in different animal species
The synthesis of bifluranol, a new fluorinated bibenzyl anti-androgen, and of 3H-labelled bifluranol is described. The absorption, distribution and excretion of bifluranol has been studied in mouse, rat, ferret and dog; it is readily absorbed following oral administration, but blood concentrations of the drug are low due to hepatic uptake and biliary excretion. Enterohepatic re-circulation occurs, but the drug is excreted primarily in the faeces and only small amounts appear in urine. This pattern of disposition and excretion is similar to that reported elsewhere for the bibenzyl, hexoestrol, and for the stilbene, diethylstilboestrol.