Frentizole

CAS# 26130-02-9

Frentizole

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Chemical structure

Frentizole

3D structure

Chemical Properties of Frentizole

Cas No. 26130-02-9 SDF Download SDF
PubChem ID 33334 Appearance Powder
Formula C15H13N3O2S M.Wt 299.35
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : ≥ 3 mg/mL (10.02 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 1-(6-methoxy-1,3-benzothiazol-2-yl)-3-phenylurea
SMILES COC1=CC2=C(C=C1)N=C(S2)NC(=O)NC3=CC=CC=C3
Standard InChIKey JHBWYQRKOUBPCA-UHFFFAOYSA-N
Standard InChI InChI=1S/C15H13N3O2S/c1-20-11-7-8-12-13(9-11)21-15(17-12)18-14(19)16-10-5-3-2-4-6-10/h2-9H,1H3,(H2,16,17,18,19)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Frentizole

DescriptionFrentizole, an FDA-approved immunosuppressive drug, is a novel inhibitor of the Aβ-ABAD interaction. IC50 value: Target: Aβ-ABAD interaction

References:
[1]. I I Scheetz ME, D G Carlson, and M R Schinitsky 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. Infec [2]. Hatfield SM, Hartley LW, Schmidtke JR. The immunomodulatory action of frentizole, a novel immunosuppressive agent. Immunopharmacology. 1982 Dec;5(2):169-79. [3]. Xie, Yuli; Deng, Shixian; Chen, Zhenzhang et al. Identification of small-molecule inhibitors of the Aβ-ABAD interaction. Bioorganic & Medicinal Chemistry Letters (2006), 16(17), 4657-4660.

Frentizole Dilution Calculator

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Preparing Stock Solutions of Frentizole

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.3406 mL 16.7029 mL 33.4057 mL 66.8114 mL 83.5143 mL
5 mM 0.6681 mL 3.3406 mL 6.6811 mL 13.3623 mL 16.7029 mL
10 mM 0.3341 mL 1.6703 mL 3.3406 mL 6.6811 mL 8.3514 mL
50 mM 0.0668 mL 0.3341 mL 0.6681 mL 1.3362 mL 1.6703 mL
100 mM 0.0334 mL 0.167 mL 0.3341 mL 0.6681 mL 0.8351 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Frentizole

Frentizole, an FDA-approved immunosuppressive drug, as a novel inhibitor of the Aβ-ABAD interaction.

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References on Frentizole

Synthesis and evaluation of frentizole-based indolyl thiourea analogues as MAO/ABAD inhibitors for Alzheimer's disease treatment.[Pubmed:28082069]

Bioorg Med Chem. 2017 Feb 1;25(3):1143-1152.

Alzheimer's disease (AD) is a neurodegenerative disorder associated with an excessive accumulation of amyloid-beta peptide (Abeta). 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 6.34muM and 0.30muM, 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.

Prolonged lifespans in female NZB/NZW mice treated with the experimental immunoregulatory drug frentizole.[Pubmed:6982717]

Arthritis Rheum. 1982 Nov;25(11):1291-7.

Autoimmune female New Zealand Black/New Zealand White mice were treated with Frentizole, an experimental immunosuppressive drug. Three groups of "young," 8-week-old mice received high-dose Frentizole (80-84 mg/kg/day), low-dose Frentizole (8 mg/kg/day), or no drug (controls); these mice were followed until spontaneous death. Three groups of "old," 24-week-old mice with established lupus-like disease were treated with high or low doses of Frentizole. Old control mice received no drug. After 12 weeks of therapy, surviving old mice were killed. Beneficial therapeutic response was achieved when high-dose treatment was started at an early age; antiDNA values were suppressed, and longevity was prolonged significantly. Frentizole did not arrest the progression of renal disease in old mice. Glomerulonephritis and vasculitis were the most common causes of death in young and old animals. Twenty-nine percent of young, high-dose-treated mice died with neoplasms. Large glomerular deposits of IgG, IgM, and C3 were present in renal tissue from treated and control mice. Peripheral lymphocyte counts and mitogenic responses of spleen cells were not changed by treatment. The efficacy of Frentizole in a murine model of lupus supports its usefulness as an immunoregulatory drug.

The immunomodulatory action of frentizole, a novel immunosuppressive agent.[Pubmed:7161058]

Immunopharmacology. 1982 Dec;5(2):169-79.

The in vitro effects of Frentizole and methylprednisolone on human PBL were examined. Both drugs exhibited differential effects on lymphocyte subpopulations. Frentizole was more effective in suppressing human lymphocytes responding to Con A and PWM, than it was in cells activated by PHA, specific antigen, or alloantigen. Methylprednisolone, on the other hand, was more inhibitory for cells stimulated by PHA, specific antigen, or alloantigen. These data suggest that Frentizole has a preferential effect on the cytotoxic/suppressor subpopulation of human T lymphocytes while methylprednisolone appears to preferentially affect the helper/inducer subset. Differences in potency between the two drugs were also observed. Methylprednisolone was better able to maintain its inhibitory effects during longer periods of culture than Frentizole. Both agents were less effective if their addition to the culture was delayed 24-48 hrs and neither drug was very effective in overcoming the adjuvant action of poly A:U on mitogenically activated human PBL.

Comparative effects of azathioprine, cyclophosphamide and frentizole on cellular immunity in mice.[Pubmed:6978364]

J Immunopharmacol. 1981;3(2):133-70.

This report extends previous observations on the immunosuppressive properties of cyclophosphamide (CPA), azathioprine and Frentizole (15) to include murine models of cellular immunity. Systemic and local graft vs host reactions (GVHR) were most effectively suppressed by CPA. In contrast to Frentizole, both CPA and azathioprine were found to inhibit the proliferation of parental T-cells in a systemic GVHR. However, CPA was the only agent capable of inhibiting the proliferation of T-cells following contact sensitization with oxazolone. Mice pretreated with a high dose of CPA or Frentizole prior to inoculation with the murine sarcoma virus exhibited accelerated tumor growth. However, there was no accelerated growth of murine sarcoma virus induced tumors or an SaI spindle cell fibrosarcoma during rather prolonged therapy with immunosuppressive doses of CPA, azathioprine or Frentizole. Normal mice treated with CPA showed a more drastic reduction in lymphoid elements of the spleen and thymus than mice treated with azathioprine or Frentizole. Studies on the mitogenic responsiveness of spleen cells obtained from normal mice after an eight day course of therapy suggested that CPA has some selectivity of action on B-cells and azathioprine on T-cells.

Description

Frentizole, an FDA-approved immunosuppressive drug, is a novel inhibitor of the Aβ-ABAD interaction.

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