15-Sep News Our Top Choice Compound: C5H8O2

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Review of zonisamide development in Japan

Zonisamide is a benzisoxazole-based compound first synthesized in the early 1970s by the research laboratories of Dainippon Pharmaceutical Company in Osaka, Japan. Identified as an anticonvulsant during exploratory research, zonisamide has since been characterized as having broad-spectrum antiepitepsy and neuroprotective effects. Early clinical studies in Japan demonstrated that zonisamide has a long elimination half-life and is well tolerated; Phase II and III clinical trials established the drug’s efficacy and safety for the treatment of partial and generalized seizures. In 1989, zonisamide was approved and marketed in Japan under the trade name of Excegran(R). Data from postmarketing surveillance studies and clinical observations over 10 years of use have continued to support zonisamide’s efficacy and safety, identified its usefulness as monotherapy, and characterized its effectiveness for various seizure types and epilepsy syndromes. (C) 2004 Published by Elsevier Ltd on behalf of BEA Trading Ltd.

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Reference:
Benzisoxazole – Wikipedia,
,Benzisoxazole – an overview | ScienceDirect Topics

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1,2-benzisoxazole phosphorodiamidates as novel anticancer prodrugs requiring bioreductive activation

Several 1,2-benzisoxazole phosphorodiamidates have been designed as prodrugs of phosphoramide mustard requiring bioreductive activation. Enzymatic reduction of 1,2-benziosoxazole moiety is expected to result in the formation of imine intermediate due to the cleavage of the N-O bond. The imine should then be spontaneously hydrolyzed to a ketone metabolite, thereby facilitating base-catalyzed beta-elimination of cytotoxic phosphoramide mustard. As expected, the proposed prodrugs 4, 9, and 12 were at least 3-5-fold more potent cytotoxins than control compounds 5 and 15, which lack in the phosphoramide mustard group. Upon incubation with phenobarb-induced rat liver S-9 fraction, compounds 4, 9, and 12 underwent extensive NADPH-dependent metabolism with concomitant generation of alkylating activity under both hypoxic and oxic conditions. Corresponding ketone metabolites were detected for 9 and 15. NADPH-dependent bioreduction of 15 to its ketone metabolite 16 was located in the microsomal fraction and inhibited by SKF-525A and pCMBA. Compared with phenobarb-induced rat liver microsomal fraction, incubation of 15 with rat or human P450 reductase microsomes showed moderate generation of 16. Microsomal cytochrome P450 and/or P450 reductase appear to be involved in the reductive metabolism of 1,2-benzisoxazole moiety under hypoxic as well as oxic conditions.

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The reaction of [2,1]benzisoxazole-4,7-quinones 1 and naphth[2,3-c]isoxazole-4,9-quinone 4 with phosphines leads to phosphoranylideneaminoquinones 2 and 5, respectively, in good to excellent yields.

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A quantitative structure-reactivity relationship (QSRR) study of the decarboxylation rates of 6-nitrobenzisoxazole-3-carboxylic acid (Kemp, D. S.; Paul, K. G. J. Am. Chem. Sec. 1975, 97, 7305). employing the CODESSA program correlates the effect of 24 solvents with theoretical descriptors to provide a straightforward interpretation of these solvent effects in terms of molecular parameters.

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Benzisoxazole – Wikipedia,
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3 Sep 2021 News More research is needed about C5H8O2

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The absorption, metabolism, and excretion of the novel antipsychotic risperidone was studied in three healthy male subjects. One week after a single oral dose of 1 mg [C-14]risperidone, 70% of the administered radioactivity was recovered in the urine and 14% in the feces. Unchanged rispeddone was mainly excreted in the urine and accounted for 30, 11, and 4% of the administered dose in the poor, intermediate, and extensive metabolizer of debrisoquine, respectively. Alicyclic hydroxylation at the 9-position of the tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one moiety was the main metabolic pathway. The active metabolite 9-hydroxy-risperidone accounted for 8, 22, and 32% of the administered dose in the urine of the poor, intermediate, and extensive metabolizer, respectively. Oxidative N-dealkylation st the piperidine nitrogen, whether or not in combination with the 9-hydroxylation, accounted for 10-13% of the dose. In methanolic extracts of feces, risperidone, and benzisoxazole-opened risperidone and hydroxylated metabolites were detected. 9-Hydroxy-risperidone was by far the main plasma metabolite. The sum of risperidone and 9-hydroxy-risperidone accounted for the largest part of the plasma radioactivity in the three subjects. Although the debrisoquine-type genetic polymorphism plays a distinct role in the metabolism of risperidone, the pharmacokinetics of the active fraction (is. risperidone plus 9-hydroxy-risperidone) remained similar among the three subjects.

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Sep 2021 News Interesting scientific research on C5H8O2

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We tested the morphogenetic and cell elongating activity of 1,2-benzisoxazole-3-one, a compound similar to 1,2-benzisoxazole-3-acetic acid but lacking the lateral carbon chain. For comparison, we tested also the activity of indole-2,3-dione, having the same indolic ring as indole-3-acetic acid but no lateral carbon chain. The tests were made on the regeneration of tomato (Lycopersicon esculentum Miller var. Alice) from cotyledons and on pea (Pisum sativum L. var. Alaska) stem elongation. We found that 1,2-benzisoxazole-3-one retains part of the high shoot inducing activity of 1,2-benzisoxazole-3-acetic acid, while indole-2,3-dione is inactive. Both compounds have no effect on root induction or cell elongation. It seems therefore that the activity of 1,2-benzisoxazole-3-acetic acid is partly related to the structure of its ring, and that also in this respect 1,2-benzisoxazole-3-acetic acid differs from other auxin-like compounds.

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A series of heterocyclic quinones based on benzofuran, benzothiophene, indazole and benzisoxazole has been synthesized, and evaluated for their ability to function as substrates for recombinant human NAD(P)H:quinone oxidoreductase (NQO1), a two-electron reductase upregulated in tumor cells. Overall, the quinones are excellent substrates for NQO1, approaching the reduction rates observed for menadione. (C) 2013 Elsevier Ltd. All rights reserved.

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A series of 3-(2-thienyl)- and 3-(1-imidazolyl)-1,2-benzisoxazoles as well as some isomeric benzoxazoles were synthesized and tested in vitro for their inhibitory effect on arachidonic acid-induced human platelet aggregation. The most active compound (7-methoxy-3-(2-thienyl)-1,2-benzisoxazole 5c) was nearly 20-30-fold more potent than acetylsalicylic acid in inhibiting platelet aggregation. Structure-activity relationships within the series are briefly discussed.

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Objectives: Zonisamide (ZnS) is a new generation antiepileptic agent used in the treatment of epilepsy patients with partial and generalized seizures. In this study, we aim to investigate the safety and efficacy of ZnS in the treatment of patients with refractory epilepsy who were being followed. Methods: Forty-five refractory epilepsy patients who received ZnS treatment were included in this study. Patients who received ZnS treatment for less than six months were excluded. Age, sex, types of seizures, examination findings, magnetic resonance imaging and electroencephalography findings, concurrent use of non-ZnS antiepileptic drugs, decrease in the seizure frequency and side effects of the drug were recorded. Results: Thirty-nine patients, whose mean age was 34.3 +/- 9.3 years, were evaluated. Complex partial seizures (CPS) and generalized tonic-clonic seizure (GTCS) were observed in 74.4% of the patients, whereas 10.3% had GTCS alone, 7.7% had CPS alone, 5.2% had GTCS and myoclonia and 2.6% of them had absence and myoclonia. In the follow-up, treatment was observed to be discontinued in 19 of the 39 patients due to drug side effects, or where there was an increase, or no change, in seizure frequency. Twenty patients responded to treatment. Seizure frequency was decreased by 25% in one patient; 50% in five patients, and 75% in seven patients. Three patients were seizure-free. Although there was no change in seizure frequency, seizure duration was shortened in four patients. Treatment-responsive patients were using ZnS at doses that ranged from 100 to 400 mg/day for 7 to 80 months. Conclusion: ZnS is a safe, tolerable and effective option for the additional treatment of refractory epilepsy patients at our center.

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New Advances in Chemical Research in 2021. Enzyme inhibitors cause a decrease in the reaction rate of an enzyme-catalyzed reaction by binding to a specific portion of an enzyme and thus slowing or preventing a reaction from occurring. 3721-95-7, Name is Cyclobutanecarboxylic acid, SMILES is O=C(C1CCC1)O, in an article , author is MANNENS, G, once mentioned of 3721-95-7, HPLC of Formula: https://www.ambeed.com/products/3721-95-7.html.

The absorption, metabolism, and excretion of the novel antipsychotic risperidone was studied in three healthy male subjects. One week after a single oral dose of 1 mg [C-14]risperidone, 70% of the administered radioactivity was recovered in the urine and 14% in the feces. Unchanged rispeddone was mainly excreted in the urine and accounted for 30, 11, and 4% of the administered dose in the poor, intermediate, and extensive metabolizer of debrisoquine, respectively. Alicyclic hydroxylation at the 9-position of the tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-one moiety was the main metabolic pathway. The active metabolite 9-hydroxy-risperidone accounted for 8, 22, and 32% of the administered dose in the urine of the poor, intermediate, and extensive metabolizer, respectively. Oxidative N-dealkylation st the piperidine nitrogen, whether or not in combination with the 9-hydroxylation, accounted for 10-13% of the dose. In methanolic extracts of feces, risperidone, and benzisoxazole-opened risperidone and hydroxylated metabolites were detected. 9-Hydroxy-risperidone was by far the main plasma metabolite. The sum of risperidone and 9-hydroxy-risperidone accounted for the largest part of the plasma radioactivity in the three subjects. Although the debrisoquine-type genetic polymorphism plays a distinct role in the metabolism of risperidone, the pharmacokinetics of the active fraction (is. risperidone plus 9-hydroxy-risperidone) remained similar among the three subjects.

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Reference:
Benzisoxazole – Wikipedia,
,Benzisoxazole – an overview | ScienceDirect Topics