Bephenium
目录号 : GC35496
Bephenium是一钩虫感染、蛔虫病治疗驱虫剂；B型乙酰胆碱受体激活剂。
Cas No.:7181-73-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Bephenium is an anthelmintic agent formerly used in the treatment of hookworm infections and ascariasis; B-type AChR activator.
[1]. JAYEWARDENE G, et al. Bephenium hydroxynaphthoate in treatment of ascariasis. Br Med J. 1960 Jul 23;2(5194):268-71. [2]. Charvet CL, et al. Selective effect of the anthelmintic bephenium on Haemonchus contortus levamisole-sensitive acetylcholine receptors. Invert Neurosci. 2012 Jun;12(1):43-51.
| Cas No. | 7181-73-9 | SDF | |
| Canonical SMILES | C[N+](CCOC1=CC=CC=C1)(C)CC2=CC=CC=C2 | ||
| 分子式 | C17H22NO | 分子量 | 256.36 |
| 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 | 3.9008 mL | 19.5038 mL | 39.0076 mL |
| 5 mM | 0.7802 mL | 3.9008 mL | 7.8015 mL |
| 10 mM | 0.3901 mL | 1.9504 mL | 3.9008 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。
Selective effect of the anthelmintic Bephenium on Haemonchus contortus levamisole-sensitive acetylcholine receptors
Invert Neurosci 2012 Jun;12(1):43-51.PMID:22526556DOI:10.1007/s10158-012-0130-0.
Acetylcholine receptors (AChRs) are pentameric ligand-gated ion channels involved in the neurotransmission of both vertebrates and invertebrates. A number of anthelmintic compounds like levamisole and pyrantel target the AChRs of nematodes producing spastic paralysis of the worms. The muscle AChRs of nematode parasites fall into three pharmacological classes that are preferentially activated by the cholinergic agonists levamisole (L-type), nicotine (N-type) and Bephenium (B-type), respectively. Despite a number of studies of the B-type AChR in parasitic species, this receptor remains to be characterized at the molecular level. Recently, we have reconstituted and functionally characterized two distinct L-AChR subtypes of the gastro-intestinal parasitic nematode Haemonchus contortus in the Xenopus laevis oocyte expression system by providing the cRNAs encoding the receptor subunits and three ancillary proteins (Boulin et al. in Br J Pharmacol 164(5):1421-1432, 2011). In the present study, the effect of the Bephenium drug on Hco-L-AChR1 and Hco-L-AChR2 subtypes was examined using the two-microelectrode voltage-clamp technique. We demonstrate that Bephenium selectively activates the Hco-L-AChR1 subtype made of Hco-UNC-29.1, Hco-UNC-38, Hco-UNC-63, Hco-ACR-8 subunits that is more sensitive to levamisole than acetylcholine. Removing the Hco-ACR-8 subunit produced the Hco-L-AChR2 subtype that is more sensitive to pyrantel than acetylcholine and partially activated by levamisole, but which was bephenium-insensitive indicating that the bephenium-binding site involves Hco-ACR-8. Attempts were made to modify the subunit stoichiometry of the Hco-L-AChR1 subtype by injecting five fold more cRNA of individual subunits. Increased Hco-unc-29.1 cRNA produced no functional receptor. Increasing Hco-unc-63, Hco-unc-38 or Hco-acr-8 cRNAs did not affect the pharmacological characteristics of Hco-L-AChR1 but reduced the currents elicited by acetylcholine and the other agonists. Here, we provide the first description of the molecular composition and functional characteristics of any invertebrate bephenium-sensitive receptor.
Activation of Caenorhabditis elegans Levamisole-Sensitive and Mammalian Nicotinic Receptors by the Antiparasitic Bephenium
Mol Pharmacol 2018 Nov;94(5):1270-1279.PMID:30190363DOI:10.1124/mol.118.113357.
Nicotinic acetylcholine receptors (nAChRs) are ligand-gated ion channels involved in neuromuscular transmission. In nematodes, muscle nAChRs are targets of antiparasitic drugs. Bephenium is an anthelmintic compound whose molecular action in the free-living nematode Caenorhabditis elegans, which is a model for anthelmintic drug discovery, is poorly known. We explored the effect of Bephenium on C. elegans locomotion and applied single-channel recordings to identify its molecular target, mechanism of action, and selectivity between mammalian and C. elegans nAChRs. As in parasites, Bephenium paralyzes C. elegans A mutant strain lacking the muscle levamisole-sensitive nAChR (L-AChR) shows full resistance to Bephenium, indicating that this receptor is the target site. Bephenium activates L-AChR channels from larvae muscle cells in the micromolar range. Channel activity is similar to that elicited by levamisole, appearing mainly as isolated brief openings. Our analysis revealed that Bephenium is an agonist of L-AChR and an open-channel blocker at higher concentrations. It also activates mammalian muscle nAChRs. Opening events are significantly briefer than those elicited by ACh and do not appear in activation episodes at a range of concentrations, indicating that it is a very weak agonist of mammalian nAChRs. Recordings in the presence of ACh showed that Bephenium acts as a voltage-dependent channel blocker and a low-affinity agonist. Molecular docking into homology-modeled binding-site interfaces represent the binding mode of Bephenium that explains its partial agonism. Given the great diversity of helminth nAChRs and the overlap of their pharmacological profiles, unraveling the basis of drug receptor-selectivity will be required for rational design of anthelmintic drugs.
Pyrantel Embonate And Bephenium Hydroxynaphthoate In The Treatment Of Hookworm Infection
Kisaengchunghak Chapchi 1975 Jun;13(1):19-30.PMID:12913463DOI:10.3347/kjp.1975.13.1.19.
A total of 100 hookworm infested patients were divided into two groups. One group of 49 received pyrantel embonate in a single oral dose of 10 mg as the base per kg body weight and the other group of 51 a single oral dose of 5.0 gm Bephenium hydroxynaphthoate for a comparison of efficacy on hookworm infestation and other intestinal helminths. Forty-two(85.7%) cases of hookworm treated with pyrantel embonate were cured and there was a 99.9 per cent mean reduction in fecal egg count. Of the 51 patients who received Bephenium hydroxynaphthoate complete cure occurred in 76.5 per cent and the mean reduction in fecal egg count was 91.8 per cent. These results plus the lower incidence of side effects recorded in the pyrnatel group suggest that pyrantel embonate is the more desirable trestment. Pyrantel embonate was highly effective against Ascaris lumbricoides, Trichostrongylus orientalis and both drugs were moderately effective against Trichuris trichiura. During the course of the study measurements of hematology, biochemistry and examinations of urine specimens were carried out. All values were normal throughout the study and no significant difference was observed between pyrantel embonate and Bephenium hydroxynaphthoate treated subjects. Side effects were more common in the Bephenium hydroxynaphthoate treated group.
Evaluation of albendazole, pyrantel, Bephenium, pyrantel-praziquantel and pyrantel-bephenium for single-dose mass treatment of necatoriasis
Ann Trop Med Parasitol 1989 Dec;83(6):625-9.PMID:2619378DOI:10.1080/00034983.1989.11812397.
An effective drug for single-dose mass treatment of necatoriasis was sought by testing three drugs and two drug combinations in Ethiopian immigrants to Israel found to have light infections. The drugs tested sequentially in single-doses were pyrantel pamoate (20 mg kg-1, 81 subjects); Bephenium hydroxynaphthoate (2.5-5 g, 65 subjects); combined pyrantel and Bephenium (25 subjects); combined pyrantel (20 mg kg-1) and praziquantel (40 mg kg-1) (16 subjects); and albendazole (400 mg, 77 subjects). Follow-up under conditions without likelihood of reinfection was by one stool examination. Cure rates with albendazole, pyrantel-bephenium and pyrantel-praziquantel were 84, 80 and 81% respectively; these rates were significantly higher than the 49% found for Bephenium and the 51% for pyrantel (P less than 0.05). Egg reductions in those not cured were pyrantel (22%), Bephenium (6%), pyrantel-bephenium (34%), pyrantel-praziquantel (3%) and albendazole (6%). Albendazole was the most promising single drug treatment; unexpected was the high effectiveness of pyrantel-praziquantel in combination.
A comparative study of the relative efficacy of pyrantel pamoate, Bephenium hydroxynaphthoate and tetrachlorethylene in the treatment of Necator americanus infection in Ceylon
Ann Trop Med Parasitol 1975 Jun;69(2):233-9.PMID:1155990DOI:10.1080/00034983.1975.11687006.
The clearance of hookworm (Necator americanus) ova by a single dose of tetrachlorethylene (T.C.E.) was compared with that produced by single and multiple dose regimes of Bephenium hydroxynaphthoate and pyrantel pamoate. Single doses of Bephenium and pyrantel were inferior to T.C.E. Three daily doses of Bephenium or pyrantel produced effects comparable with a single dose of T.C.E. Because of the low cost and lack of side effects, T.C.E. remains the drug of choice in the treatment of N. americanus in infections; the only disadvantage of T.C.E. is its unnoticed deterioration under tropical conditions.