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Journal articles on the topic 'Phenothiazines'

Author: Grafiati

Published: 4 June 2021

Last updated: 9 February 2022

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1

Durst, R., P. Rosca-Rebaudengo, and D. Admon. "Phenothiazine-Associated Supraventricular Tachycardia." Australian & New Zealand Journal of Psychiatry 28, no. 2 (June 1994): 333–36. http://dx.doi.org/10.1080/00048679409075649.

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Psychotropic medications, mainly phenothiazines, are known to be associated with cardiac insult. The case report presented here describes nearly fatal arrhythmia (sustained supraventricular tachycardia) consequent to phenothiazine treatment. The authors aim to alert psychiatrists to the possible adverse, and even fatal, effects of phenothiazines.

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2

Dixit, Yogesh, Rahul Dixit, Naveen Gautam, and D. C. Gautam. "Synthesis of Bioactive Fluorinated 10H-Phenothiazines and their Sulfone Derivatives." E-Journal of Chemistry 5, s1 (2008): 1063–68. http://dx.doi.org/10.1155/2008/809419.

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The present communication deals with the synthesis of a series of fluorinated 10H-phenothiazines. 10H-phenothiazines is prepared by Smiles rearrangement of substituted 2-foramido-2´-nitrodiphenylsulfide. Substituted 2-foramido-2´-nitrodiphenylsulfide were obtained by the reaction of 2-amino-3-fluorobenzenethiol witho-halonitrobenzenes followed by formylation and 1-nitro/1-halo-10H-phenothiazines have been prepared by the reaction of substituted 2-aminobenzenethiols with reactiveo-halonitrobenzene containing a nitro group or halogen atom ato-position to the reactive halogen atom directly yielded 1-nitro/1-halo-10H-phenothiazines in situ. 10H-phenothiazine sulfone derivatives have been synthesized by the oxidation of 10H-phenothiazines by 30% hydrogen peroxide in glacial acetic acid. The structure of the synthesized compounds has been characterized by spectroscopic data and elemental analysis. Antimicrobial studies of the synthesized compounds have also been included.

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3

Khadieva, Alena I., Vladimir V. Gorbachuk, and Ivan I. Stoikov. "Oligomerization of phenothiazin-5-ium tetraiodide in the presence of bases." Butlerov Communications 62, no. 6 (June 30, 2020): 34–39. http://dx.doi.org/10.37952/roi-jbc-01/20-62-6-34.

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Methylene blue and its structural analogs (phenothiazine derivatives) are well known photodynamically and photochemically active agents, which are used in modern medicine, biology, and industry due to their low toxicity, high absorption in the therapeutic window region (600-660 nm). Methylene blue being one of the most studied phenothiazine derivative is employed as an antibacterial agent and also as an antidote to cyanide, carbon monoxide and hydrogen sulfide. Phenothiazin-5-ium tetraiodide is one of the most convenient precursors for the synthesis of structural analogues of methylene blue among the variety of modern synthetic approaches. Nucleophilic addition of aromatic and aliphatic amines to phenothiazin-5-ium tetraiodide can be used to obtain a wide range of 3,7-phenothiazine-5-ium derivatives. The specificities of addition reactions of dialkylamines and aromatic amines to phenothiazin-5-ium tetraiodide are low yields and formation of difficultly separable mixtures of products. It was found that reactions of phenathiazin-5-ium tetraiodide with amines containing secondary and tertiary amino groups lead to oligomerization of phenathiazin-5-ium tetraiodide (3,10-positions). Basicity of tertiary amino group is crucial in oligomerization of phenathiazin-5-ium tetraiodide. It is shown, that triethylamine use as a base allows to synthesize of oligo(3,10)phenothiazines with high yields. According to 1Н, 13C NMR, IR spectroscopy data and MALDI mass-spectrometry data, thereaction product is a mixture of oligomers, consisting mainly of three to four units.

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4

Chan, Ying Ying, Yong Mei Ong, and Kim Lee Chua. "Synergistic Interaction between Phenothiazines and Antimicrobial Agents against Burkholderia pseudomallei." Antimicrobial Agents and Chemotherapy 51, no. 2 (December 4, 2006): 623–30. http://dx.doi.org/10.1128/aac.01033-06.

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ABSTRACT The gram-negative soil bacillus Burkholderia pseudomallei is the causative agent of melioidosis, a severe and potentially fatal septicemic disease that is endemic to Southeast Asia and northern Australia. Its intrinsic resistance to many antibiotics is attributed mainly to the presence of several drug efflux pumps, and therefore, inhibitors of such pumps are expected to restore the activities of many clinically important antimicrobial agents that are the substrates of these pumps. The phenothiazine antipsychotic and antihistaminic drugs prochlorperazine, chlorpromazine, and promazine have a synergistic interaction with a wide spectrum of antimicrobial agents, thereby enhancing their antimicrobial potency against B. pseudomallei. Antimicrobial agents that interacted synergistically with the phenothiazines include streptomycin, erythromycin, oleandomycin, spectinomycin, levofloxacin, azithromycin, and amoxicillin-clavulanic acid. The MICs of these antibiotics were reduced as much as 8,000-fold in the presence of the phenothiazines. Antimicrobial agents which did not interact synergistically with the phenothiazines include gentamicin, amoxicillin, and ampicillin. Omeprazole, a proton pump inhibitor, provided an augmentation of antimicrobial activities similar to that of the phenothiazines, suggesting that the phenothiazines might have interfered with the proton gradient at the inner membrane. B. pseudomallei cells accumulated more erythromycin in the presence of the phenothiazines, an effect similar to that of carbonyl cyanide m-chlorophenylhydrazone, a proton gradient uncoupler. In the presence of the phenothiazines, a much reduced concentration of erythromycin (0.06× MIC) also protected human lung epithelial cells and macrophage cells from B. pseudomallei infection and attenuated its cytotoxicity.

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5

Young, Allan, and Robert Kehoe. "Two Cases of Agranulocytosis on Addition of a Butyrophenone to a Long-Standing Course of Phenothiazine Treatment." British Journal of Psychiatry 154, no. 5 (May 1989): 710–12. http://dx.doi.org/10.1192/bjp.154.5.710.

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Two cases of agranulocytosis occurring after addition of a butyrophenone to a course of phenothiazine treatment are reported and possible mechanisms for this interaction are discussed. Agranulocytosis is a well-documented adverse effect of phenothiazine administration (Vincent, 1986). Important factors are the total amount of drug given and the duration of administration. Agranulocytosis usually occurs within the first three months of therapy (Pisciotta, 1971; Marcus & Mulvihill, 1978) and the relationship with the cumulative dose has been emphasised (Ananth et al, 1973). Agranulocytosis following prolonged administration has been rarely reported (Denber, 1970, Pisciotta, 1978). We report two cases where agranulocytosis developed in patients with a long previous exposure to phenothiazines, treated for the first time with a combination of phenothiazines and a butyrophenone.

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6

Wu, San, Wei-Ye Hu, and Song-Lin Zhang. "Potassium carbonate-mediated tandem C–S and C–N coupling reaction for the synthesis of phenothiazines under transition-metal-free and ligand-free conditions." RSC Advances 6, no. 29 (2016): 24257–60. http://dx.doi.org/10.1039/c6ra01295g.

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A potassium carbonate-mediated tandem coupling reaction for the synthesis of phenothiazines is described. This protocol affords an efficient approach for the construction of phenothiazine derivatives without the need for addition of transition-metal catalyst or ligand.

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7

Schmidt, Maximilian, Mathias Hermann, Fabian Otteny, and Birgit Esser. "Calix[n]phenothiazines: Optoelectronic and Structural Properties and Host–Guest Chemistry." Organic Materials 02, no. 03 (July 2020): 235–39. http://dx.doi.org/10.1055/s-0040-1714295.

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Calixarenes are of interest as receptors for ions and small molecules and as organic materials. Exchanging the arene units through heteroaromatics allows changing their optoelectronic and host–guest properties. We herein present calix[n]phenothiazines (n = 3, 4) as novel macrocycles, accessible in two-step syntheses. The phenothiazine units show reversible redox events and emissive properties, and N-hexyl-substituted calix[3]phenothiazine binds to both ammonium ions and a bisimidazole as neutral guests.

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8

Parkash, Ram, Hari Om Gupta, and Jatinder Dutt. "Chronopotentiometric studies of certain biologically important compounds at tubular graphite electrode." Collection of Czechoslovak Chemical Communications 56, no. 9 (1991): 1833–37. http://dx.doi.org/10.1135/cccc19911833.

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The chronopotentiometric studies of certain phenothiazines in hydrodynamic systems at a solution flow-through tubular graphite electrode were carried out in sulfuric acid of different concentrations. A well-defined single wave (involving 2 electrons) in 0.1M H2SO4 and two waves (involving 1 electron each) in 2.0M H2SO4 were observed. Phenothiazines are oxidized trough the formation of a monocation radical by the elimination of one electron from the lone pair of N-atom. The monocation radical is stable in sulfuric acid of a moderate concentration and is unstable in neutral or less acidic solutions. The cation radical undergoes instantaneous hydrolysis yielding sulfoxide, thus presenting an overall two-electron oxidation of the phenothiazine derivatives. The suitability of the chronopotentiometric technique for their determination was established.

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9

&NA;. "Phenothiazines." Reactions Weekly &NA;, no. 428 (November 1992): 11. http://dx.doi.org/10.2165/00128415-199204280-00055.

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10

Steinbrecher, Kurt, C. A. Brunner, J. M. Newton, R. T. Newton, M. L. Robinette, A. Santiago, H. S. Scroggins, U. Sics, and E. J. Wojtowicz. "Thin Layer Chromatographic Identification of Phenothiazine Derivative Drugs: Interlaboratory Study." Journal of AOAC INTERNATIONAL 69, no. 6 (November 1, 1986): 1030–34. http://dx.doi.org/10.1093/jaoac/69.6.1030.

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Abstract A thin layer chromatographic method for the identification of phenothiazine derivative drugs was studied collaboratively by 8 laboratories. Twenty phenothiazine drugs were examined by each collaborator. The identification scheme depends on the color of the sprayed spots and the Rf values relative to the Rf of chlorpromazine (RCHL) in 4 solvent systems. In 98.13% of the cases, a correct identification could be made; the remaining drugs were reduced to a choice between pairs of phenothiazines. With respect to chlorpromazine, the data showed a significant decrease in variability of RCHL values compared with Rf values in the 4 solvent systems.

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11

Khelwati, Hilla, Adam W. Franz, Zhou Zhou, Werner R. Thiel, and Thomas J. J. Müller. "Triazolyl Conjugated (Oligo)Phenothiazines Building Blocks for Hybrid Materials—Synthesis and Electronic Properties." Molecules 26, no. 10 (May 15, 2021): 2950. http://dx.doi.org/10.3390/molecules26102950.

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The Cu-catalyzed alkyne-azide 1,3-dipolar cycloaddition variant provides a highly efficient entry to conjugated triazolyl-substituted (oligo)phenothiazine organosilicon derivatives with luminescence and reversible redox characteristics. Furthermore, by in-situ co-condensation synthesis several representative mesoporous MCM-41 type silica hybrid materials with embedded (oligo)phenothiazines are prepared and characterized with respect to their structural and electronic properties. The hybrid materials also can be oxidized to covalently bound embedded radical cations, which are identified by their UV/Vis absorption signature and EPR signals.

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12

&NA;. "Phenothiazines/butyrophenones." Reactions Weekly &NA;, no. 309 (July 1990): 7. http://dx.doi.org/10.2165/00128415-199003090-00029.

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13

&NA;. "Phenothiazines/haloperidol." Reactions Weekly &NA;, no. 354 (June 1991): 11. http://dx.doi.org/10.2165/00128415-199103540-00051.

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14

Kafafy, Hany, Hongwei Wu, Ming Peng, Hsienwei Hu, Kai Yan, Reda M. El-Shishtawy, and Dechun Zou. "Steric and Solvent Effect in Dye-Sensitized Solar Cells Utilizing Phenothiazine-Based Dyes." International Journal of Photoenergy 2014 (2014): 1–9. http://dx.doi.org/10.1155/2014/548914.

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Three phenothiazine-based dyes have been prepared and utilized as dye-sensitized solar cells (DSSCs). The effects of dye-adsorption solvent on the performances of dye-sensitized solar cells based on phenothiazine dyes were investigated in this study. The highest conversion efficiency of 3.78% was obtained using ethanol (EtOH) and 2.53% for tetrahydrofuran (THF), respectively, as dye-adsorption solvents. Cell performance using EtOH as a dye-adsorption solvent showed relatively higher performance than that using THF. Electrochemical and photochemical tests of phenothiazine dyes in solution and adsorbed on the TiO2surface showed less dye loading and coverage on the TiO2surface during adsorption in the case of THF, which decreased the solar cell performance of the DSSC using THF as adsorption solvent compared with using EtOH as adsorption solvent. Meanwhile, the steric effect of phenothiazine-based (PT1–3) dyes was also investigated. Dye with longer and branched aliphatic chain in the order ofPT1,PT2, andPT3showed an increased resistance of the recombination reaction and electron lifetime, thereby increasingVocand enhancing the overall cell performance because of the sterically hindered conformation of the phenothiazines.

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15

Alexandrovsky, V. N., S. S. Petrikov, and M. V. Kareva. "Acute poisoning with phenothiazine neuroleptics. Phenothiazine coma." Toxicological Review, no. 3 (July 18, 2021): 16–27. http://dx.doi.org/10.36946/0869-7922-2021-29-3-16-27.

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The article summarizes the authors' long-term experience in the diagnosis and treatment of acute poisoning with phenothiazine derivatives and presents data on the epidemiology of the effects of phenothiazines on the central nervous system. The original classification of acute phenothiazine intoxication confirmed by electrophysiological studies of the brain is given. The involvement of deep brain structures in the pathogenesis of acute phenothiazine coma has been confirmed. Based on studies of visual evoked potentials, the absence of inhibition of deep brain structures despite a pronounced comatose state is shown. In some cases, repeated light stimulation provoked hypersynchronization of evoked potentials and the appearance of convulsive manifestations in the clinic, which was regarded as a state of parabiosis (according to N.E. Vvedensky). Emergency treatment measures for phenothiazine poisoning associated with accelerated detoxification of the body mainly using active methods such as peritoneal dialysis, intestinal lavage with constant monitoring of respiratory function and the cardiovascular system, are presented. The materials of the article will help doctors of intensive care and toxicology departments to improve the quality of diagnosis and treatment of these pathologies.

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16

Bailey, Andrew M., Ian T. Paulsen, and Laura J. V. Piddock. "RamA Confers Multidrug Resistance in Salmonella enterica via Increased Expression of acrB, Which Is Inhibited by Chlorpromazine." Antimicrobial Agents and Chemotherapy 52, no. 10 (August 11, 2008): 3604–11. http://dx.doi.org/10.1128/aac.00661-08.

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ABSTRACT Salmonella enterica serovar Typhimurium SL1344, in which efflux pump genes (acrB, acrD, acrF, tolC) or regulatory genes thereof (marA, soxS, ramA) were inactivated, was grown in the presence of 240 antimicrobial and nonantimicrobial agents in the Biolog Phenotype MicroArray. Mutants lacking tolC, acrB, and ramA grew significantly worse than other mutants in the presence of 48 agents (some of which have not previously been identified as substrates of AcrAB-TolC) and particularly poorly in the presence of phenothiazines, which are human antipsychotics. MIC testing revealed that the phenothiazine chlorpromazine had antimicrobial activity and synergized with common antibiotics against different Salmonella serovars and SL1344. Chlorpromazine increased the intracellular accumulation of ethidium bromide, which was ablated in mutants lacking acrB, suggesting an interaction with AcrB. High-level but not low-level overexpression of ramA increased the expression of acrB; conferred resistance to chloramphenicol, tetracycline, nalidixic acid, and triclosan and organic solvent tolerance; and increased the amount of ethidium bromide accumulated. Chlorpromazine induced the modest overproduction of ramA but repressed acrB. These data suggest that phenothiazines are not efflux pump inhibitors but influence gene expression, including that of acrB, which confers the synergy with antimicrobials observed.

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17

Poła, Andrzej, Anna Palko-Łabuz, and Kamila Środa-Pomianek. "Theoretical Study of 2-(Trifluoromethyl)phenothiazine Derivatives with Two Hydroxyl Groups in the Side Chain-DFT and QTAIM Computations." Molecules 26, no. 17 (August 29, 2021): 5242. http://dx.doi.org/10.3390/molecules26175242.

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Phenothiazines are known as synthetic antipsychotic drugs that exhibit a wide range of biological effects. Their properties result from the structure and variability of substituents in the heterocyclic system. It is known that different quantum chemical properties have a significant impact on drug behavior in the biological systems. Thus, due to the diversity in the chemical structure of phenothiazines as well as other drugs containing heterocyclic systems, quantum chemical calculations provide valuable methods in predicting their activity. In our study, DFT computations were applied to show some thermochemical parameters (bond dissociation enthalpy—BDE, ionization potential—IP, proton dissociation enthalpy—PDE, proton affinity—PA, and electrontransfer enthalpy—ETE) describing the process of releasing the hydrogen/proton from the hydroxyl group in the side chain of four 2-(trifluoromethyl)phenothiazine (TFMP) derivatives and fluphenazine (FLU). Additional theoretical analysis was carried out based on QTAIM theory. The results allowed theoretical determination of the ability of compounds to scavenge free radicals. In addition, the intramolecular hydrogen bond (H-bond) between the H-atom of the hydroxyl group and the N-atom located in the side chain of the investigated compounds has been identified and characterized.

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18

Tarapdar, Abed, James K. S. Norris, Oliver Sampson, Galina Mukamolova, and James T. Hodgkinson. "The design and synthesis of an antibacterial phenothiazine–siderophore conjugate." Beilstein Journal of Organic Chemistry 14 (October 16, 2018): 2646–50. http://dx.doi.org/10.3762/bjoc.14.242.

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Siderophore–antibiotic conjugates consist of an antibiotic covalently linked by a tether to a siderophore. Such conjugates can demonstrate enhanced uptake and internalisation to the bacterial cell resulting in significantly reduced MIC values and extended spectrum of activity. Phenothiazines are a class of small molecules that have been identified as a potential treatment for multidrug resistant tuberculosis and latent TB. Herein we report the design and synthesis of the first phenothiazine–siderophore conjugate. A convergent synthetic route was developed whereby the functionalised phenothiazine component was prepared in four steps and the siderophore component also prepared in four steps. In M. smegmatis the functionalised phenothiazine demonstrated an equipotent MIC value in direct comparison to the parent phenothiazine from which it was derived. The final conjugate was synthesised by amide bond formation between the two components and global deprotection of the PMB protecting groups to unmask the catechol iron chelating groups of the siderophore. The synthesis is readily amenable to the preparation of analogues whereby the siderophore component of the conjugate can be modified. The route will be used to prepare a library of siderophore–phenothiazine conjugates for full biological evaluation of much needed new antibacterial agents.

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19

Wu, Yan-Chen, Shuai-Shuai Jiang, Ren-Jie Song, and Jin-Heng Li. "A metal- and oxidizing-reagent-free anodic para-selective amination of anilines with phenothiazines." Chemical Communications 55, no. 30 (2019): 4371–74. http://dx.doi.org/10.1039/c9cc01332f.

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20

Edwards, Rod, Una Stephenson, and Tom Flewett. "Clonazepam in Acute Mania: A Double Blind Trial." Australian & New Zealand Journal of Psychiatry 25, no. 2 (June 1991): 238–42. http://dx.doi.org/10.3109/00048679109077740.

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In a double-blind trial involving acutely manic patients, clonazepam was compared to placebo, both groups receiving chlorpromazine as needed. The group receiving clonazepam showed significantly more improvement in their manic but not their psychotic symptoms compared to the placebo group. This effect was not primarily related to the sedative effects of clonazepam. Clonazepam tended to reduce the need for phenothiazine medication. Side effects related to sedation were more common to the clonazepam group. These findings are the first to indicate that clonazepam may have a specific antimanic effect over and above that of phenothiazines alone.

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21

Środa-Pomianek, Kamila, Krystyna Michalak, Anna Palko-Łabuz, Anna Uryga, Piotr Świątek, Michał Majkowski, and Olga Wesołowska. "The Combined Use of Phenothiazines and Statins Strongly Affects Doxorubicin-Resistance, Apoptosis, and Cox-2 Activity in Colon Cancer Cells." International Journal of Molecular Sciences 20, no. 4 (February 22, 2019): 955. http://dx.doi.org/10.3390/ijms20040955.

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Since none of the multidrug resistance (MDR) modulators tested so far found their way into clinic, a novel approach to overcome the MDR of cancer cells has been proposed. The combined use of two MDR modulators of dissimilar mechanisms of action was suggested to benefit from the synergy between them. The effect of three phenothiazine derivatives that were used as single agents and in combination with simvastatin on cell growth, apoptosis induction, activity, and expression of cyclooxygenase-2 (COX-2) in doxorubicin-resistant colon cancer cells (LoVo/Dx) was investigated. Treatment of LoVo/Dx cells by phenothiazine derivatives combined with simvastatin resulted in an increase of doxorubicin cytotoxicity and its intracellular accumulation as compared to the treatment with phenothiazine derivatives that were used as single agents. Similarly, LoVo/Dx cells treated with two-component mixture of modulators showed the reduced expression of ABCB1 (P-glycoprotein) transporter and COX-2 enzyme, both on mRNA and protein level. Reduced expression of anti-apoptotic Bcl-2 protein and increased expression of pro-apoptotic Bax were also detected. Additionally, COX-2 activity was diminished, and caspase-3 activity was increased to a higher extent by phenothiazine derivative:simvastatin mixtures than by phenothiazine derivatives themselves. Therefore, the introduction of simvastatin strengthened the anti-MDR, anti-inflammatory, and pro-apoptotic properties of phenothiazines in LoVo/Dx cells.

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22

&NA;. "Carbamazepine/haloperidol/phenothiazines." Reactions Weekly &NA;, no. 1268 (September 2009): 12. http://dx.doi.org/10.2165/00128415-200912680-00036.

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23

&NA;. "Phenothiazines/tricyclic antidepressants." Reactions Weekly &NA;, no. 1236 (January 2009): 28. http://dx.doi.org/10.2165/00128415-200912360-00079.

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24

Birkett, D. Peter. "Phenothiazines in Dementia." Journal of the American Geriatrics Society 38, no. 12 (December 1990): 1380. http://dx.doi.org/10.1111/j.1532-5415.1990.tb03465.x.

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25

Kiselyuk, Alice, Suzette Farber-Katz, Tom Cohen, Seung-Hee Lee, Ifat Geron, Behrad Azimi, Susanne Heynen-Genel, et al. "Phenothiazine Neuroleptics Signal to the Human Insulin Promoter as Revealed by a Novel High-Throughput Screen." Journal of Biomolecular Screening 15, no. 6 (June 14, 2010): 663–70. http://dx.doi.org/10.1177/1087057110372257.

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A number of diabetogenic stimuli interact to influence insulin promoter activity, making it an attractive target for both mechanistic studies and therapeutic interventions. High-throughput screening (HTS) for insulin promoter modulators has the potential to reveal novel inputs into the control of that central element of the pancreatic β-cell. A cell line from human islets in which the expression of insulin and other β-cell-restricted genes are modulated by an inducible form of the bHLH transcription factor E47 was developed. This cell line, T6PNE, was adapted for HTS by transduction with a vector expressing green fluorescent protein under the control of the human insulin promoter. The resulting cell line was screened against a library of known drugs for those that increase insulin promoter activity. Members of the phenothiazine class of neuroleptics increased insulin gene expression upon short-term exposure. Chronic treatment, however, resulted in suppression of insulin promoter activity, consistent with the effect of phenothiazines observed clinically to induce diabetes in chronically treated patients. In addition to providing insights into previously unrecognized targets and mechanisms of action of phenothiazines, the novel cell line described here provides a broadly applicable platform for mining new molecular drug targets and central regulators of β-cell differentiated function.

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26

Youssef, Adel F., Salwa R. El-Shabouri, Fardous A. Mohamed, and Abdel Maboud I. Rageh. "Colorimetric Determination of Certain Phenothiazine Drugs by Using Morpholine and Iodine-Potassium Iodide Reagents." Journal of AOAC INTERNATIONAL 69, no. 3 (May 1, 1986): 513–18. http://dx.doi.org/10.1093/jaoac/69.3.513.

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Abstract A colorimetric method was developed for the quantitative estimation of 11 phenothiazine drugs. The method is based on the interaction of unsulfoxidized drug with morpholine and iodine-potassium iodide reagents. The interaction for all studied phenothiazine drugs yields a blue product with 2 absorption maxima: one in the range of 620-640 nm with lower molar absorptivity and the other in the range of 662-690 nm with higher molar absorptivity. The color was stable for at least 10 h. The reproducibility and recovery of the method were excellent. The method was applied successfully to the analysis of various commercially available phenothiazines in different dosage forms. The results were comparable to those obtained by official procedures. The suitability of the method for detection and estimation of promethazine excreted in urine has been suggested by preliminary experiments. Reaction products have been isolated and identified.

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27

Rabkin, Marshall. "Rapid Microchemical Identification of Four Phenothiazine Antiemetics with Gold Bromide and Iodine-Potassium Iodide Reagents: Collaborative Study." Journal of AOAC INTERNATIONAL 68, no. 3 (May 1, 1985): 527–29. http://dx.doi.org/10.1093/jaoac/68.3.527.

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Abstract A microchemical method was developed for the rapid identification of 4 phenothiazine antiemetics. Perphenazine, promethazine, thiethylperazine, and triflupromazine were positively identified and differentiated with the aid of a gold bromide reagent and an iodine-potassium iodide reagent. Only promethazine and triflupromazine yielded microcrystalline derivatives with gold bromide; only perphenazine and thiethylperazine reacted with iodine-potassium iodide. For each pair of positive reactions, the crystalline products were morphologically distinguishable under a microscope. The 2 tests were collaboratively studied by 7 independent laboratories and found to be simple, rapid, and effective for identifying the phenothiazines of interest. The method has been adopted official first action

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28

Shinmen, Natsuko, Xiao-Pen Lee, Takeshi Kumazawa, Chika Hasegawa, Yasuhiro Ishiwata, Keizo Sato, Hiroshi Seno, and Osamu Suzuki. "Simultaneous Determination of Some Phenothiazine Derivatives in Human Blood by Headspace Solid-Phase Microextraction and Gas Chromatography with Nitrogen-Phosphorus Detection." Journal of AOAC INTERNATIONAL 91, no. 6 (November 1, 2008): 1354–62. http://dx.doi.org/10.1093/jaoac/91.6.1354.

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Abstract Chlorpromazine, levomepromazine, promazine, triflupromazine, and trimeprazine were simultaneously determined in human whole blood and plasma by combining headspace solid-phase microextraction and gas chromatography with nitrogenphosphorus detection. Extraction efficiency for the phenothiazine derivatives was 0.0130.117 for both sample types. Regression equations were linear [correlation coefficient (r) 0.99510.9999] within the range 2.5200 ng/0.5 mL for triflupromazine and trimeprazine, and 6.3200 ng/0.5 mL for chlorpromazine, levomepromazine, and promazine. The limit of detection for each compound was 0.23.9 ng/0.5 mL whole blood and plasma. Intraday and interday coefficients of variation for all phenothiazines in both human samples were commonly <15 and 20, respectively. We also report the determination of levomepromazine in human plasma after oral administration.

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29

JAIN, M., S. K. GUPTA, V. SARASWAT, and R. R. GUPTA. "ChemInform Abstract: Phenothiazines. Part 19. Synthesis of Phenothiazines via Smiles Rearrangement." ChemInform 26, no. 7 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199507175.

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30

Lal, Manohar, and H. S. Mahal. "Reactions of thiyl radicals with phenothiazines and other antioxidants in aqueous solutions. A pulse radiolysis study." Canadian Journal of Chemistry 68, no. 8 (August 1, 1990): 1376–82. http://dx.doi.org/10.1139/v90-211.

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Reaction rate constants of thiyl radicals with phenothiazines, promethazine (PMZ), chlorpromazine (CPZ), prochlorperazine (PPZ), trimeperazine tarterate (TPZ), and other antioxidants, e.g., ascorbic acid and 2,2-azinobis(3-ethyl benzthiazoline-6 sulphonate) (ABTS) have been estimated using pulse radiolysis technique. In general they are quite high (108–109 M−1 s−1). The k values for cysteine, cysteamine, mercaptoethanol, and mercaptopropionic acid with similar structures and molecular weights are more or less similar for PMZ, CPZ, and PPZ.Rate constants are lower in value for [Formula: see text] radicals of phenothiazines showing that they are dependent upon the structure and the molecular weight of the compound.Rate constants are the same whether the thiyl radicals are generated from thiols or their corresponding disulphides. The k values for chlorine-containing phenothiazines, chlorpromazine, and prochlorperazine are higher than those of promothazine Keywords: pulse radiolysis, thiyl radicals, phenothiazines, ABTS, ascorbic acid.

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31

Chignell, C. F., A. G. Motten, and G. R. Buettner. "Photoinduced free radicals from chlorpromazine and related phenothiazines: relationship to phenothiazine-induced photosensitization." Environmental Health Perspectives 64 (December 1985): 103–10. http://dx.doi.org/10.1289/ehp.8564103.

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32

&NA;. "Butyrophenones see Phenothiazines/butyrophenones." Reactions Weekly &NA;, no. 309 (July 1990): 4. http://dx.doi.org/10.2165/00128415-199003090-00011.

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33

Motohashi, Noboru, Masami Kawase, Kazue Satoh, and Hiroshi Sakagami. "Cytotoxic Potential of Phenothiazines." Current Drug Targets 7, no. 9 (September 1, 2006): 1055–66. http://dx.doi.org/10.2174/138945006778226624.

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34

&NA;. "Haloperidol see Phenothiazines/haloperidol." Reactions Weekly &NA;, no. 354 (June 1991): 9. http://dx.doi.org/10.2165/00128415-199103540-00035.

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35

Motohashi, Noboru, Sitaraghav R. Gollapudi, Jahangir Emrani, and Kesava R. Bhattiprolu. "Antitumor Properties of Phenothiazines." Cancer Investigation 9, no. 3 (January 1991): 305–19. http://dx.doi.org/10.3109/07357909109021328.

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36

Hamer, David. "Phenothiazines and community care." International Psychiatry 8, no. 4 (November 2011): 101–2. http://dx.doi.org/10.1192/s1749367600002812.

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37

Bhopal, Jaswant Singh. "Comment: Phenothiazines and Hirsutism." DICP 24, no. 11 (November 1990): 1124. http://dx.doi.org/10.1177/106002809002401131.

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38

Warman, A. J., T. S. Rito, N. E. Fisher, D. M. Moss, N. G. Berry, P. M. O'Neill, S. A. Ward, and G. A. Biagini. "Antitubercular pharmacodynamics of phenothiazines." Journal of Antimicrobial Chemotherapy 68, no. 4 (December 9, 2012): 869–80. http://dx.doi.org/10.1093/jac/dks483.

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39

Bigal, Marcelo E. "Phenothiazines in Migraine Treatment." Current Pain and Headache Reports 14, no. 4 (May 19, 2010): 253–55. http://dx.doi.org/10.1007/s11916-010-0116-8.

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40

CZARNY, ANNA, EWA ZACZYŃSKA, MAŁGORZATA JELEŃ, MICHAŁ ZIMECKI, KRYSTIAN PLUTA, BEATA MORAK-MŁODAWSKA, JOLANTA ARTYM, and MAJA KOCIĘBA. "Antimicrobial Properties of Substituted quino[3,2-b]benzo[1,4]thiazines." Polish Journal of Microbiology 63, no. 3 (2014): 335–39. http://dx.doi.org/10.33073/pjm-2014-044.

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Our previous studies demonstrated that among phenothiazines several derivatives could be found showing strong antiproliferative actions and the property of inhibiting inducible tumor necrosis factor alpha (TNF a) production in human blood cultures. The aim of this investigation was to determine potential antimicrobial actions of forty four new phenothiazine derivatives with the quinobenzothiazine structure. The compounds showed differential antibacterial and antifungal activities against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Candida albicans depending on the compound structures, concentrations and bacterial strains. More specifically, 6-(1-methyl- 2-piperidylethyl) quinobenzothiazine displayed strongest actions against S. aureus and E. coli whereas 6-methanesulfonylaminobutyl-9-methylthioquinobenzothiazine exhibited the most universal antimicrobial properties. The correlation between antimicrobial activity and the chemical structure of quinobenzothiazines was discussed.

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Otręba, Michał, Johanna Johansson Sjölander, Morten Grøtli, and Per Sunnerhagen. "A Small Molecule Targeting Human MEK1/2 Enhances ERK and p38 Phosphorylation under Oxidative Stress or with Phenothiazines." Life 11, no. 4 (March 31, 2021): 297. http://dx.doi.org/10.3390/life11040297.

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Small molecules are routinely used to inhibit protein kinases, but modulators capable of enhancing kinase activity are rare. We have previously shown that the small molecule INR119, designed as an inhibitor of MEK1/2, will enhance the activity of its fission yeast homologue, Wis1, under oxidative stress. To investigate the generality of these findings, we now study the effect of INR119 in human cells under similar conditions. Cells of the established breast cancer line MCF-7 were exposed to H2O2 or phenothiazines, alone or combined with INR119. In line with the previous results in fission yeast, the phosphorylation of the MAPKs ERK and p38 increased substantially more with the combination treatment than by H2O2 or phenothiazines, whereas INR119 alone did not affect phosphorylation. We also measured the mRNA levels of TP53 and BAX, known to be affected by ERK and p38 activity. Similarly, the combination of INR119 and phenothiazines increased both mRNAs to higher levels than for phenothiazines alone. In conclusion, the mechanism of action of INR119 on its target protein kinase may be conserved between yeast and humans.

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Hipkiss, Jayne B., A. Skinner, and C. J. Branford White. "Biochemical and ultrastructural investigation of the effect of Stelazine (trifluoperazine) on Hymenolepis diminuta (Cestoda)." Parasitology 94, no. 1 (February 1987): 135–49. http://dx.doi.org/10.1017/s003118200005352x.

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SUMMARYThe effects of the phenothiazine, Stelazine, on Hymenolepis diminuta were investigated. The cestode was incubated for 10 min at 37 °C with 1 mM trifluoperazine, in the presence and absence of Ca2+. Assay of brush border enzymes showed that drug treatment lowered the activities of alkaline phosphatase, Ca2+-ATP'ase, 5′-nucleotidase and type 1 phosphodiesterase. This occurred in parallel with a significant reduction in tegumental protein. Under these conditions gross changes in ultrastructural appearance and cellular organization were observed. There was a lack of ordered microtriches and the distal cytoplasm was absent. Glycogen granules were scattered throughout the cytoplasm within the subtegumental layer. The connective tissue also appeared to be in some disarray. The effects of Stelazine appeared to be dependent on time and were significantly increased when Ca2+ was included in the incubation medium. Incubation with the less hydrophobic phenothiazine trifluoperazine sulphoxide had minimal effect on the integrity of the cestode. The results reported here support the premise that certain phenothiazines may be considered as potential cestocidal agents.

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Buene, Audun Formo, Mats Christensen, and Bård Helge Hoff. "Effect of Auxiliary Donors on 3,8-Phenothiazine Dyes for Dye-Sensitized Solar Cells." Molecules 24, no. 24 (December 7, 2019): 4485. http://dx.doi.org/10.3390/molecules24244485.

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Phenothiazines are one of the more common dye scaffolds for dye-sensitized solar cells. However, these sensitizers are exclusively based on a 3,7-substitution pattern. Herein, we have synthesized and characterized novel 3,8-substituted phenothiazine dyes in order to evaluate the effect of auxiliary donor groups on the performance of this new dye class. The power conversion efficiency increased by 7%–10% upon insertion of an auxiliary donor in position 8 of the phenothiazine, but the structure of the auxiliary donor (phenyl, naphthyl, pyrene) had a low impact when electrodes were stained with chenodeoxycholic acid (CDCA) additive. In the absence of CDCA, the highest power conversion efficiency was seen for the phenyl-based sensitizer attributed to a higher quality dye-monolayer. By comparing the novel dyes to their previously reported 3,7- analogues, only subtle differences were seen in photophysical, electrochemical, and performance measurements. The most notable difference between the two geometries is a lowering of the oxidation potentials of the 3,8-dyes by 40–50 mV compared to the 3,7-analogues. The best auxiliary donor for the 3,8-phenothiazine dyes was found to be pyrenyl, with the best device delivering a power conversion efficiency of 6.23% (99 mW cm−2, 10 eq. CDCA, JSC = 10.20 mA cm−2, VOC = 791 mV, and FF = 0.765).

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Puzanowska-Tarasiewicz, Helena, Joanna Karpińska, and Ludmiła Kuźmicka. "Analytical Applications of Reactions of Iron(III) and Hexacyanoferrate(III) with 2,10-Disubstituted Phenothiazines." International Journal of Analytical Chemistry 2009 (2009): 1–8. http://dx.doi.org/10.1155/2009/302696.

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The presented review is devoted to analytical applications of reactions of Fe(III) and with 2,10-disubstituted phenothiazines (PT). It was found that iron(III) and hexacyanoferrate(III) ions in acidic media easily oxidized PT with the formation of colored oxidation products. This property has been exploited for spectrophotometric determination of iron(III) ions and phenothiazines. Some flow-injection procedures of the determination of PT based on the oxidation reaction by means of the above-mentioned oxidants have been proposed. In the presented review, the application of 2,10-disubstituted phenothiazines as indicators in complexometric titration of iron(III) as well as procedures of PT determination based on generation of ternary compound in the system Fe(III)-- PT was also described.

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45

Choo, Hea-Young P., Yunsuk O. Shin, and Jongsei Park. "Study of the Metabolism of Phenothiazines: Determination of N-Demethylated Phenothiazines in Urine." Journal of Analytical Toxicology 14, no. 2 (March 1, 1990): 116–19. http://dx.doi.org/10.1093/jat/14.2.116.

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46

Jayarama, M. Violet D'Souza, H. S. Yathirajan, and Rangaswamy. "Interaction of phenothiazines with nitroso-R salt and extractive spectrophotometric determination of phenothiazine drugs." Talanta 33, no. 4 (April 1986): 352–54. http://dx.doi.org/10.1016/0039-9140(86)80087-x.

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Chamoun-Emanuelli, Ana M., Eve-Isabelle Pecheur, Rudo L. Simeon, Da Huang, Paul S. Cremer, and Zhilei Chen. "Phenothiazines Inhibit Hepatitis C Virus Entry, Likely by Increasing the Fluidity of Cholesterol-Rich Membranes." Antimicrobial Agents and Chemotherapy 57, no. 6 (March 25, 2013): 2571–81. http://dx.doi.org/10.1128/aac.02593-12.

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ABSTRACTDespite recent progress in the development of direct-acting antiviral agents against hepatitis C virus (HCV), more effective therapies are still urgently needed. We and others previously identified three phenothiazine compounds as potent HCV entry inhibitors. In this study, we show that phenothiazines inhibit HCV entry at the step of virus-host cell fusion, by intercalating into cholesterol-rich domains of the target membrane and increasing membrane fluidity. Perturbation of the alignment/packing of cholesterol in lipid membranes likely increases the energy barrier needed for virus-host fusion. A screening assay based on the ability of molecules to selectively increase the fluidity of cholesterol-rich membranes was subsequently developed. One compound that emerged from the library screen, topotecan, is able to very potently inhibit the fusion of liposomes with cell culture-derived HCV (HCVcc). These results yield new insights into HCV infection and provide a platform for the identification of new HCV inhibitors.

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Scott, Rolene, Geoffrey T. Cunningham, Jenny M. Puddle, Jeremy D. Klinger, and Robert J. Jacobs. "Ocular side effects of phenothiazines." Clinical and Experimental Optometry 74, no. 1 (January 1991): 11–14. http://dx.doi.org/10.1111/j.1444-0938.1991.tb04601.x.

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Kristiansen, Jette E., and Ida Mortensen. "Antibacterial Effect of Four Phenothiazines." Pharmacology & Toxicology 60, no. 2 (February 1987): 100–103. http://dx.doi.org/10.1111/j.1600-0773.1987.tb01504.x.

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50

Brock, C. P., P. J. DeLaLuz, M. Golinski, M. A. Lloyd, T. C. Vanaman, and D. S. Watt. "Planarity of nitro-substituted phenothiazines." Acta Crystallographica Section B Structural Science 52, no. 4 (August 1, 1996): 713–19. http://dx.doi.org/10.1107/s0108768196000201.

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The structures of three nitro-substituted phenothiazines [1,3,4-trifluoro-2-nitrophenothiazine, 10-(4-chlorobutyl)-1,3,4-trifluoro-2-nitrophenothiazine and 10-(4-chlorobutyl)-3-nitrophenothiazine] have been determined. The first of these red compounds forms infinite stacks in the solid state, in which donor and acceptor regions of the approximately planar molecules alternate. The molecules of the other two compounds, which have folded, or `butterfly', conformations in the solid state, do not form stacks, presumably because the bulky chlorobutyl substituents cannot be accommodated. The very dark color of solid 3-nitrophenothiazine suggests the presence of extended molecular stacks, but crystals suitable for a structure determination could not be obtained.

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