Frentizole
(Synonyms: 夫仑替唑) 目录号 : GC36076
Frentizole (Frentizol) is a novel inhibitor of amyloid beta peptide (Abeta) binding alcohol dehydrogenase (ABAD) interaction with IC50 of 200 μM. Frentizole is a nontoxic antiviral and immunosuppressive agent used clinically in rheumatoid arthritis and systemic lupus erythematosus.
Cas No.:26130-02-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
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- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Frentizole (Frentizol) is a novel inhibitor of amyloid beta peptide (Abeta) binding alcohol dehydrogenase (ABAD) interaction with IC50 of 200 μM. Frentizole is a nontoxic antiviral and immunosuppressive agent used clinically in rheumatoid arthritis and systemic lupus erythematosus.
[1] Xie Y, et al. Bioorg Med Chem Lett. 2006 Sep 1;16(17):4657-60.
| Cas No. | 26130-02-9 | SDF | |
| 别名 | 夫仑替唑 | ||
| Canonical SMILES | O=C(NC1=CC=CC=C1)NC2=NC3=CC=C(OC)C=C3S2 | ||
| 分子式 | C15H13N3O2S | 分子量 | 299.35 |
| 溶解度 | DMSO: ≥ 3 mg/mL (10.02 mM) | 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 | 3.3406 mL | 16.7029 mL | 33.4057 mL |
| 5 mM | 0.6681 mL | 3.3406 mL | 6.6811 mL |
| 10 mM | 0.3341 mL | 1.6703 mL | 3.3406 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。
Frentizole therapy in systemic lupus erythematosus
Arthritis Rheum 1980 Dec;23(12):1376-80.PMID:7006612DOI:10.1002/art.1780231208.
Seven corticosteroid dependent patients with active systemic lupus erythematosus (SLE) were given Frentizole in order to assess its effect on their clinical manifestations. Three patients exhibited slight clinical improvement, 2 patients did not change, and 2 deteriorated. Five of the 7 patients developed subclinical and reversible liver damage related to Frentizole. This study, although preliminary and uncontrolled, suggests that Frentizole is of limited value in the management of patients with SLE.
Frentizole therapy of active systemic lupus erythematosus
Arthritis Rheum 1980 Dec;23(12):1381-7.PMID:7006613DOI:10.1002/art.1780231209.
Frentizole is a benzimidazoleurea that has immunosuppressive properties in mice. Eleven steroid-treated patients with active systemic lupus erythematosus received Frentizole (150-350 mg/day) in combination with stable or decreasing doses of prednisone in an open label trial. Nine patients completed at least one 21- to 75-day course of therapy with this drug. Clinical parameters of disease improved in 8 of these 9 patients. Mean DNA binding decreased by 28%, mean CH50 increased by 20%, and mean absolute lymphocyte and T cell counts decreased by 25-26%. Granulocytopenia was not observed. Three patients developed reversible hepatic toxicity. Clinical and serologic improvement was noted in 3 patients who accepted a second 90-day course of Frentizole therapy.
Synthesis and Biological Importance of 2-(thio)ureabenzothiazoles
Molecules 2022 Sep 19;27(18):6104.PMID:36144837DOI:10.3390/molecules27186104.
The (thio)urea and benzothiazole (BT) derivatives have been shown to have a broad spectrum of biological activities. These groups, when bonded, result in the 2-(thio)ureabenzothizoles (TBT and UBT), which could favor the physicochemical and biological properties. UBTs and TBTs are compounds of great importance in medicinal chemistry. For instance, Frentizole is a UBT derivative used for the treatment of rheumatoid arthritis and systemic lupus erythematosus. The UBTs Bentaluron and Bethabenthiazuron are commercial fungicides used as wood preservatives and herbicides in winter corn crops. On these bases, we prepared this bibliography review, which covers chemical aspects of UBTs and TBTs as potential therapeutic agents as well as their studies on the mechanisms of a variety of pharmacological activities. This work covers synthetic methodologies from 1935 to nowadays, highlighting the most recent approaches to afford UBTs and TBTs with a variety of substituents as illustrated in 42 schemes and 13 figures and concluded with 187 references. In addition, this interesting review is designed on chemical reactions of 2-aminobenzothiazoles (2ABTs) with (thio)phosgenes, iso(thio)cyanates, 1,1'-(thio)carbonyldiimidazoles [(T)CDI]s, (thio)carbamoyl chlorides, and carbon disulfide. This topic will provide information of utility for medicinal chemists dedicated to the design and synthesis of this class of compounds to be tested with respect to their biological activities and be proposed as new pharmacophores.
Frentizole, a novel immunosuppressive, and azathioprine: their comparative effects on host resistance to Pseudomonas aeruginosa, Candida albicans, herpes simplex virus, and influenza (Ann Arbor) virus
Infect Immun 1977 Jan;15(1):145-8.PMID:188761DOI:10.1128/iai.15.1.145-148.1977.
Frentizole, 1-(6-methoxy-2-benzothiazolyl)-3-phenyl urea, a new immunosuppressive agent, and azathioprine were administered subcutaneously at predetermined immunosuppressive dose levels of azathioprine and up to 50 times an immunosuppressive dose level of Frentizole. After 10 days of treatment at these dose levels, the experimental groups were inoculated intraperitoneally with Pseudomonas aeruginosa or herpes simplex virus, inoculated intraveneously with Candida albicans, or infected by aerosol with Ann Arbor influenza virus. The results of these series of experiments indicate that Frentizole, even at super immunosuppressive doses, does not predispose the hose (mice) to Pseudomonas aeruginosa, Candida albicans, herpes simplex virus, or Ann Arbor influenza virus.
Synthesis and evaluation of frentizole-based indolyl thiourea analogues as MAO/ABAD inhibitors for Alzheimer's disease treatment
Bioorg Med Chem 2017 Feb 1;25(3):1143-1152.PMID:28082069DOI:10.1016/j.bmc.2016.12.029.
Alzheimer's disease (AD) is a neurodegenerative disorder associated with an excessive accumulation of amyloid-beta peptide (Aβ). Based on the multifactorial nature of AD, preparation of multi-target-directed ligands presents a viable option to address more pathological events at one time. A novel class of asymmetrical disubstituted indolyl thioureas have been designed and synthesized to interact with monoamine oxidase (MAO) and/or amyloid-binding alcohol dehydrogenase (ABAD). The design combines the features of known MAO inhibitors scaffolds (e.g. rasagiline or ladostigil) and a Frentizole moiety with potential to interact with ABAD. Evaluation against MAO identified several compounds that inhibited in the low to moderate micromolar range. The most promising compound (19) inhibited human MAO-A and MAO-B with IC50 values of 6.34μM and 0.30μM, respectively. ABAD activity evaluation did not show any highly potent compound, but the compound series allowed identification of structural features to assist the future development of ABAD inhibitors. Finally, several of the compounds were found to be potent inhibitors of horseradish peroxidase (HRP), preventing the use of the Amplex™ Red assay to detect hydrogen peroxide produced by MAO, highlighting the need for serious precautions when using an enzyme-coupled assay.