Nitazoxanide
M. Lindsay Grayson, Sara E. Cosgrove, Suzanne M. Crowe, M. Lindsay Grayson, William Hope, James S. McCarthy, John Mills, Johan W. Mouton, David L. Paterson in Kucers’ The Use of Antibiotics, 2017
Nitazoxanide is a nitrothiazolyl–salicylamide derivative and belongs to the thiazolide class. The chemical structure is 2-acetyloxy-N-(5-nitro-2-thiazolyl) benzamide, and the molecular formula is C12H9N3O5S (Figure 186.1). The molecular weight is 307.28 g/mol. The benzamide structure resembles niclosamide, a drug used to treat tapeworm infections, whereas the nitrothiazolyl ring shares homology with the nitroimidazole drugs metronidazole and tinidazole (see Chapter 99, Metronidazole, and Chapter 100, Tinidazole). Nitazoxanide was first described in 1975 by Jean Francois Rossignol at the Pasteur Institute in Paris, France, and originally was developed as a veterinary anthelmintic. Initial human studies in the 1980s revealed its efficacy in treating human tapeworm infections (Rossignol and Maisonneuve, 1984). Subsequent in vitro and clinical studies have demonstrated an unusually broad antimicrobial spectrum that transcends taxonomic classes, with activity against protozoan parasites, helminths, anaerobic bacteria, mycobacteria, and viruses. A series of controlled trials conducted by Romark Laboratories established the efficacy of nitazoxanide for the treatment of giardiasis and cryptosporidiosis in immunocompetent patients, leading to approval in the United States for the treatment of Cryptosporidium species and also Giardia infections. The drug is also approved in many Latin American and Asian countries for the treatment of a range of intestinal helminths.
Psychopharmacology EMIs
Michael Reilly, Bangaru Raju in Extended Matching Items for the MRCPsych Part 1, 2018
Each option may be used once, more than once or not at all.For each of the following statements about adverse effects of antipsychotics, choose the drug above that is most likely to be implicated.A common side-effect of this thienobenzodiazepine atypical antipsychotic is weight gain.This dibenzothiazepine atypical antipsychotic is not associated with any significant increase in serum prolactin levels.This substituted benzamide antipsychotic is thought to have a dose-dependant action at presynaptic dopamine sites.This diphenylbutylpiperidine is the longest-acting per oral administered antipsychotic.
Pharmacology
Bhaskar Punukollu, Michael Phelan, Anish Unadkat in MRCPsych Part 1 In a Box, 2019
Classification of antipsychoticsTypicals: Phenothiazines – chlorpromazine (aliphatic side chains), thioridazine (piperidine), trifluoperazine (piperazine), fluphenazine. Thioxanthenes – flupenthixol, zuclopenthixol. Butyrophenones – haloperidol, droperidol. Diphenylbutylpiperidines – pimozide. Substituted benzamides – sulpiride.Atypicals: Dibenzodiazepines – clozapine. Thienobenzodiazepine – olanzapine. Dibenzothiazepine – quetiapine. Benzisoxoles – risperidone. Imidazolidinedione – sertindole.
Preparation and evaluation of polyphenol derivatives as potent antifouling agents: addition of a side chain affects the biological activity of polyphenols
Published in Biofouling, 2022
Xuan Wang, Xiaohui Jiang, Liangmin Yu
N-(2,3,4-Trihydroxy-5-benzamidemethylbenzyl)benzamide (b4): white solid, yield: 93.54%, m.p. 187.3 ∼ 191.2 °C. IR (KBr) ν: 702.69, 1100.09, 1329.12, 1444.35, 1487.92, 1554.15, 1633.15, 2933.88, 3062.36, 3383.95 cm−1; 1H NMR (DMSO, 600 MHz) δ: 4.31 (d, 2H, CH2), 4.32 (d, 2H, CH2), 6.54 (s, 1H, PhH), 7.45 (t, J = 6.00 Hz, 4H, PhH), 7.53 (m, 2H, PhH), 7.86 (t, 4H, PhH), 8.35 (s, 1H, OH), 9.08 (t, J = 6.00 Hz, 2H, NH), 9.12 (s, 2H, OH); 13C NMR (DMSO, 150 MHz) δ: 36.69, 39.11, 117.08, 117.11, 119.28, 127.76, 127.79, 127.88, 128.56, 128.75, 128.83, 131.65, 131.93, 132.02, 133.20, 134.20, 134.45, 134.60, 143.63, 145.01, 167.58, 167.87. HRMS: m/z 415.1267 ([M + Na]+, calculated for C22H20N2O5Na: 415.3947).
Zinc binding groups for histone deacetylase inhibitors
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2018
Lei Zhang, Jian Zhang, Qixiao Jiang, Li Zhang, Weiguo Song
The most significant feature of benzamide as ZBG in HDACIs is class I selectivity or individual HDAC isoform selectivity. Side effects of HDACIs are supposed to be reduced with the improvement of selectivity. The highly selective HDACIs could also serve as probe molecules in the diagnosis and pathogenetic research of diseases involving only a specific isoform of HDACs. The major disadvantage of benzamide derivatives is relatively compromised therapeutic benefits in clinical trials, which might explain the fact that, none of the benzamide HDACIs has been approved by the US FDA yet. Although high selectivity implies safety in clinical application, the exposed amino group in the benzamide structure could potentially induce in vivo toxicity41. Furthermore, tumour cells are more likely to develop drug resistance against highly selective inhibitors, which might compromise the therapeutic effects of benzamide HDACIs in long-term therapies42.
Development and characterisation of levosulpiride-loaded suppositories with improved bioavailability in vivo
Published in Pharmaceutical Development and Technology, 2019
Gul Majid Khan
Levosulpiride is a derivative of benzamide group which is potentially used for the treatment of depression and psychiatric problems. It selectively blocks D2 receptors in submucosal and myoenteric plexus (Kim et al. 2016a; Fotaki et al. 2005). Levosulpiride enhances gastric evacuation and digestive signs in patients with functional dyspepsia and diabetic gastroparesis. Moreover, it has been successfully investigated for the treatment of premature ejaculation (Greco et al. 2002; Hussain et al. 2010). Beside all the related efficacy of levosulpiride, its poorly water solubility and low permeability (BCS Class IV drug) is a big challenge in developing various formulations, including oral and injectable formulations, for its therapeutic use (Ibrahim et al. 2013). Furthermore, because of its low pKa, various excipients are required for the development of injectable formulations, which sometimes results in severe pain to the patient leading to discomfort, after injection.