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Journal articles on the topic 'Ethenzamide'

Author: Grafiati

Published: 24 April 2022

Last updated: 30 July 2025

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1

&NA;. "Ethenzamide." Reactions Weekly &NA;, no. 669 (1997): 8. http://dx.doi.org/10.2165/00128415-199706690-00023.

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2

&NA;. "Apronalide/ethenzamide." Reactions Weekly &NA;, no. 940 (2003): 6. http://dx.doi.org/10.2165/00128415-200309400-00016.

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3

Niedziejko-Ćwiertnia, Paulina, Anna Karolina Drabczyk, Damian Kułaga, et al. "Environmentally Friendly Green O-Alkylation Reaction for Ethenzamide Synthesis." Applied Sciences 15, no. 3 (2025): 1342. https://doi.org/10.3390/app15031342.

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Ethenzamide (2-ethoxybenzamide), besides acetylsalicylic acid, is one of the mostly used salicylic acid derivatives in pharmaceuticals. It has analgesic and anti-inflammatory effects that originate from the inhibition of cyclooxygenase (COX-1) activity, thus blocking prostaglandin synthesis. In this work, efficient and eco-friendly methods were developed for the synthesis of ethenzamide via the O-alkylation reaction of salicylamide. The reactions were carried out under conventional conditions in a solvent-free system using variant solvents and different phase transfer catalysts (PTC) in the pr

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4

Hsu, Yung-Tai, and Chie-Shaan Su. "Application of Box–Behnken Design to Investigate the Effect of Process Parameters on the Microparticle Production of Ethenzamide through the Rapid Expansion of the Supercritical Solutions Process." Pharmaceutics 12, no. 1 (2020): 42. http://dx.doi.org/10.3390/pharmaceutics12010042.

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In this study, the rapid expansion of the supercritical solutions (RESS) process was used to produce microparticles of a commonly used anti-inflammatory drug, ethenzamide. The effects of process parameters in RESS including the extraction temperature, pre-expansion temperature, and post-expansion temperature were investigated using the Box–Behnken design. According to the results of the analysis of variance (ANOVA), the effect of pre-expansion temperature is the most significant parameter on the mean size of RESS-produced ethenzamide. A higher pre-expansion temperature benefits the production

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5

&NA;. "Caffeine/ethenzamide/paracetamol overdose." Reactions Weekly &NA;, no. 497 (1994): 5. http://dx.doi.org/10.2165/00128415-199404970-00013.

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6

Aoki, S., A. Okamoto, K. Danjo, H. Sunada, and A. Otuka. "Compatibility of Ibuprofen and Ethenzamide." Drug Development and Industrial Pharmacy 23, no. 6 (1997): 561–65. http://dx.doi.org/10.3109/03639049709149820.

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7

Khatioda, Rajiv, Basanta Saikia, Pranab Jyoti Das, and Bipul Sarma. "Solubility and in vitro drug permeation behavior of ethenzamide cocrystals regulated in physiological pH environments." CrystEngComm 19, no. 46 (2017): 6992–7000. http://dx.doi.org/10.1039/c7ce01626c.

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Drug release behavior of few ethenzamide cocrystals was investigated at different pH buffers. Change in lipophilic behavior and conformational adjustment of drug along with supramolecular synthons were probed for their improved drug efficacy.

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8

Kawada, Akira, Masataro Hiruma, Hiromitsu Noguchi, Atsushi Aakagi, Akira Ishibashi, and Joseph Marshall. "Fixed drug eruption induced by ethenzamide." Contact Dermatitis 34, no. 5 (1996): 369–70. http://dx.doi.org/10.1111/j.1600-0536.1996.tb02231.x.

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9

Aitipamula, Srinivasulu, Pui Shan Chow, and Reginald B. H. Tan. "Trimorphs of a pharmaceutical cocrystal involving two active pharmaceutical ingredients: potential relevance to combination drugs." CrystEngComm 11, no. 9 (2009): 1823–27. http://dx.doi.org/10.1039/b904616j.

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The first example of a trimorphic cocrystal involving two active pharmaceutical ingredients, ethenzamide and gentisic acid, is reported; metastable polymorphs convert to the stable form upon solid-state grinding; pharmaceutical cocrystals involving two or more APIs have potential relevance to combination drugs.

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10

Trzeciak, Katarzyna, Ewelina Wielgus, Sławomir Kaźmierski, Tomasz Pawlak, and Marek J. Potrzebowski. "Amorphization of Ethenzamide and Ethenzamide Cocrystals—A Case Study of Single and Binary Systems Forming Low-Melting Eutectic Phases Loaded on/in Silica Gel." Pharmaceutics 15, no. 4 (2023): 1234. http://dx.doi.org/10.3390/pharmaceutics15041234.

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The applicability of different solvent-free approaches leading to the amorphization of active pharmaceutical ingredients (APIs) was tested. Ethenzamide (ET), an analgesic and anti-inflammatory drug, and two ethenzamide cocrystals with glutaric acid (GLU) and ethyl malonic acid (EMA) as coformers were used as pharmaceutical models. Calcinated and thermally untreated silica gel was applied as an amorphous reagent. Three methods were used to prepare the samples: manual physical mixing, melting, and grinding in a ball mill. The ET:GLU and ET:EMA cocrystals forming low-melting eutectic phases were

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11

Choquesillo-Lazarte, Duane, Cristóbal Verdugo-Escamilla, and Juan Manuel García-Ruiz. "Novel solid forms of the analgesic drug ethenzamide." Acta Crystallographica Section A Foundations and Advances 70, a1 (2014): C995. http://dx.doi.org/10.1107/s2053273314090044.

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The interest in multicomponent solid forms has increased in the last years within the pharmaceutical industry and also the solid-state community due to the possibility of obtaining materials with new properties [1]. Crystallization strategies, supported by solvent- and solid-based techniques, have also received attention in the search and development of methodologies for the screening of multicomponent crystals. In this work, ethenzamide, an anti-inflammatory and analgesic drug, was selected as a model drug to develop cocrystals on the basis of the synthon types using a series of phenolic cofo

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12

Lin, Shuting, Jiarong Zhang, Weijie Sun, Penghui Ren, Jiayi Jiang, and Chengjun Jiang. "New Ethenzamide-Trimesic Acid Cocrystal: Equilibrium Solubility." OALib 10, no. 06 (2023): 1–10. http://dx.doi.org/10.4236/oalib.1110247.

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13

Aitipamula, Srinivasulu, Pui Shan Chow, and Reginald B. H. Tan. "Ethenzamide–gentisic acid–acetic acid (2/1/1)." Acta Crystallographica Section E Structure Reports Online 66, no. 5 (2010): o1045—o1046. http://dx.doi.org/10.1107/s1600536810012407.

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14

Back, Kevin R., Roger J. Davey, Tudor Grecu, Christopher A. Hunter, and Lynne S. Taylor. "Molecular Conformation and Crystallization: The Case of Ethenzamide." Crystal Growth & Design 12, no. 12 (2012): 6110–17. http://dx.doi.org/10.1021/cg301244x.

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15

Sarmah, Kashyap Kumar, Kaveri Boro, Mihails Arhangelskis, and Ranjit Thakuria. "Crystal structure landscape of ethenzamide: a physicochemical property study." CrystEngComm 19, no. 5 (2017): 826–33. http://dx.doi.org/10.1039/c6ce02057g.

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16

Aitipamula, Srinivasulu, Annie B. H. Wong, Pui Shan Chow, and Reginald B. H. Tan. "Pharmaceutical cocrystals of ethenzamide: structural, solubility and dissolution studies." CrystEngComm 14, no. 24 (2012): 8515. http://dx.doi.org/10.1039/c2ce26325d.

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17

Hariprasad, Vijaya M., Sunil Kumar Nechipadappu, and Darshak R. Trivedi. "Cocrystals of Ethenzamide: Study of Structural and Physicochemical Properties." Crystal Growth & Design 16, no. 8 (2016): 4473–81. http://dx.doi.org/10.1021/acs.cgd.6b00606.

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18

YASUNO, NOBUHIRO, MASAO TSUCHIYA, JUNKO KIZU, et al. "Preparation and Clinical Application of 2% Ethenzamide Oral Ointment." Japanese Journal of Hospital Pharmacy 22, no. 6 (1996): 556–63. http://dx.doi.org/10.5649/jjphcs1975.22.556.

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19

Sarmah, Kashyap Kumar, and Ranjit Thakuria. "Crystal structure landscape of ethenzamide: their physicochemical property study." Acta Crystallographica Section A Foundations and Advances 73, a2 (2017): C441. http://dx.doi.org/10.1107/s205327331709132x.

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20

Moribe, Kunikazu, Masami Tsuchiya, Yuichi Tozuka, Kentaro Yamaguchi, Toshio Oguchi, and Keiji Yamamoto. "Grinding-Induced Equimolar Complex Formation between Thiourea and Ethenzamide." CHEMICAL & PHARMACEUTICAL BULLETIN 52, no. 5 (2004): 524–29. http://dx.doi.org/10.1248/cpb.52.524.

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21

MATSUMOTO, Kazuhiro, Yoshinobu NAKAI, Etsuo YONEMOCHI, Toshio OGUCHI, and Keiji YAMAMOTO. "Effect of Pore Size on the Gaseous Adsorption of Ethenzamide on Porous Crystalline Cellulose and the Physicochemical Stability of Ethenzamide after Storage." CHEMICAL & PHARMACEUTICAL BULLETIN 46, no. 2 (1998): 314–18. http://dx.doi.org/10.1248/cpb.46.314.

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22

Przybyłek, Maciej, Dorota Ziółkowska, Karina Mroczyńska, and Piotr Cysewski. "Propensity of salicylamide and ethenzamide cocrystallization with aromatic carboxylic acids." European Journal of Pharmaceutical Sciences 85 (March 2016): 132–40. http://dx.doi.org/10.1016/j.ejps.2016.02.010.

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23

Khatioda, Rajiv, Pranita Bora, and Bipul Sarma. "Trimorphic Ethenzamide Cocrystal: In Vitro Solubility and Membrane Efflux Studies." Crystal Growth & Design 18, no. 8 (2018): 4637–45. http://dx.doi.org/10.1021/acs.cgd.8b00603.

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24

Mapp, Lucy, Mateusz Pitak, Simon Coles, and Srinivasulu Aitipamula. "Charge density studies on 1:1 co-crystals of ethenzamide and saccharin." Acta Crystallographica Section A Foundations and Advances 70, a1 (2014): C964. http://dx.doi.org/10.1107/s2053273314090354.

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The study of multi-component crystals, as well as the phenomenon of polymorphism, both have relevance to crystal engineering. Obtaining a specific polymorph is crucial as different polymorphs usually exhibit different physical and chemical properties and often the origin of this behaviour is unknown. This is especially important in the pharmaceutical industry. Herein, we present results of comparative studies of an analgesic drug, ethenzamide and its co-crystals with saccharin. The co-crystalisation of ethenzamide (2-ethoxybenzamide, EA) with saccharin (1,1-dioxo-,1,2-benzothiazol-3-one, SAC)

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25

Saikia, Basanta, Andreas Seidel-Morgenstern, and Heike Lorenz. "Multicomponent Materials to Improve Solubility: Eutectics of Drug Aminoglutethimide." Crystals 12, no. 1 (2021): 40. http://dx.doi.org/10.3390/cryst12010040.

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Here, we report the synthesis and experimental characterization of three drug-drug eutectic mixtures of drug aminoglutethimide (AMG) with caffeine (CAF), nicotinamide (NIC) and ethenzamide (ZMD). The eutectic mixtures i.e., AMG-CAF (1:0.4, molar ratio), AMG-NIC (1:1.9, molar ratio) and AMG-ZMD (1:1.4, molar ratio) demonstrate significant melting point depressions ranging from 99.2 to 127.2 °C compared to the melting point of the drug AMG (151 °C) and also show moderately higher aqueous solubilities than that of the AMG. The results presented include the determination of the binary melt phase d

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26

Yasuno, Nobuhiro, Masao Tsuchiya, Junko Kizu, et al. "Development of Ethenzamide Ointment as a Pain Relief for Postherpetic Neuralgia." Iryo Yakugaku (Japanese Journal of Pharmaceutical Health Care and Sciences) 28, no. 4 (2002): 309–14. http://dx.doi.org/10.5649/jjphcs.28.309.

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27

Fukunaka, T., B. Golman, and K. Shinohara. "Continuous Grinding Kinetics of Ethenzamide Particles by Fluidized-Bed Jet-Milling." Drug Development and Industrial Pharmacy 32, no. 3 (2006): 347–55. http://dx.doi.org/10.1080/03639040500519136.

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28

Fukunaka, Tadashi, Boris Golman, and Kunio Shinohara. "Batch grinding kinetics of Ethenzamide particles by fluidized-bed jet-milling." International Journal of Pharmaceutics 311, no. 1-2 (2006): 89–96. http://dx.doi.org/10.1016/j.ijpharm.2005.12.018.

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29

Aitipamula, S., P. S. Chow, and R. B. H. Tan. "Polymorphism of co-crystals: co-crystal polymorphs of an analgesic drug, ethenzamide." Acta Crystallographica Section A Foundations of Crystallography 64, a1 (2008): C476—C477. http://dx.doi.org/10.1107/s0108767308084699.

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30

Przybyłek, Maciej, Anna Miernicka, Mateusz Nowak, and Piotr Cysewski. "New Screening Protocol for Effective Green Solvents Selection of Benzamide, Salicylamide and Ethenzamide." Molecules 27, no. 10 (2022): 3323. http://dx.doi.org/10.3390/molecules27103323.

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New protocol for screening efficient and environmentally friendly solvents was proposed and experimentally verified. The guidance for solvent selection comes from computed solubility via COSMO-RS approach. Furthermore, solute-solvent affinities computed using advanced quantum chemistry level were used as a rationale for observed solvents ranking. The screening protocol pointed out that 4-formylomorpholine (4FM) is an attractive solubilizer compared to commonly used aprotic solvents such as DMSO and DMF. This was tested experimentally by measuring the solubility of the title compounds in aqueou

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31

Rajbongshi, Trishna, Kashyap Kumar Sarmah, Ramesh Ganduri, Suryanarayan Cherukuvada, Mihails Arhangelskis, and Ranjit Thakuria. "Mechanosynthesis of Eutectics of Anti‐Inflammatory Drug Ethenzamide – A Comparison with Analogous Cocrystals." Chemistry–Methods 1, no. 9 (2021): 408–14. http://dx.doi.org/10.1002/cmtd.202100016.

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32

Tong, Yao, Feiyan Shi, Wenhui Wang, et al. "Experimental measurement and thermodynamic modelling of ethenzamide solubility in three binary solvent systems." Journal of Chemical Thermodynamics 161 (October 2021): 106553. http://dx.doi.org/10.1016/j.jct.2021.106553.

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33

Rajbongshi, Trishna, Kashyap Kumar Sarmah, Ramesh Ganduri, Suryanarayan Cherukuvada, Mihails Arhangelskis, and Ranjit Thakuria. "Mechanosynthesis of Eutectics of Anti‐Inflammatory Drug Ethenzamide – A Comparison with Cocrystals Analogues." Chemistry–Methods 1, no. 9 (2021): 398. http://dx.doi.org/10.1002/cmtd.202100076.

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34

Sarcevica, I., L. Orola, M. V. Veidis, and S. Belyakov. "Preparation and characterization of an anti-inflammatory drug ethenzamide cocrystals with dicarboxylic acids." Acta Crystallographica Section A Foundations of Crystallography 68, a1 (2012): s223. http://dx.doi.org/10.1107/s0108767312095670.

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35

HANAWA, Takehisa, Rieko IKOMA, Atsushi WATANABE, Masato HIDAKA, and Masayasu SUGIHARA. "Preparation and Characterization of Sealed Heated Mixture of Ethenzamide and Porous Calcium Silicate." CHEMICAL & PHARMACEUTICAL BULLETIN 44, no. 7 (1996): 1367–71. http://dx.doi.org/10.1248/cpb.44.1367.

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36

AOKI, Shinji, Taku MIZUTANI, and Kazumi DANJO. "Studies on the Number of Contacts between Ibuprofen and Ethenzamide Using Thermal Analysis." CHEMICAL & PHARMACEUTICAL BULLETIN 48, no. 1 (2000): 140–41. http://dx.doi.org/10.1248/cpb.48.140.

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37

Wan, Mei, Jiyuan Fang, Jiadan Xue, et al. "Pharmaceutical Cocrystals of Ethenzamide: Molecular Structure Analysis Based on Vibrational Spectra and DFT Calculations." International Journal of Molecular Sciences 23, no. 15 (2022): 8550. http://dx.doi.org/10.3390/ijms23158550.

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Pharmaceutical cocrystals can offer another advanced strategy for drug preparation and development and can facilitate improvements to the physicochemical properties of active pharmaceutical ingredients (APIs) without altering their chemical structures and corresponding pharmacological activities. Therefore, cocrystals show a great deal of potential in the development and research of drugs. In this work, pharmaceutical cocrystals of ethenzamide (ETZ) with 2,6-dihydroxybenzoic acid (26DHBA), 2,4-dihydroxybenzoic acid (24DHBA) and gallic acid (GA) were synthesized by the solvent evaporation metho

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38

Acebedo-Martínez, Francisco Javier, Carolina Alarcón-Payer, Jaime Gómez-Morales, Alicia Domínguez-Martín, and Duane Choquesillo-Lazarte. "Cocrystals of ethenzamide with polyphenols: solid-state characterization and preliminary evaluation of biopharmaceutical parameters." Acta Crystallographica Section A Foundations and Advances 77, a2 (2021): C798. http://dx.doi.org/10.1107/s0108767321089005.

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39

Aitipamula, Srinivasulu, Pui Shan Chow, and Reginald B. H. Tan. "Conformational and enantiotropic polymorphism of a 1 : 1 cocrystal involving ethenzamide and ethylmalonic acid." CrystEngComm 12, no. 11 (2010): 3691. http://dx.doi.org/10.1039/c004491a.

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40

DANJO, Kazumi, Tsuyoshi NAKATA, and Akinobu OTSUKA. "Preparation and Dissolution Behavior of Ethenzamide Solid Dispersions Using Various Sugars as Dispersion Carriers." CHEMICAL & PHARMACEUTICAL BULLETIN 45, no. 11 (1997): 1840–44. http://dx.doi.org/10.1248/cpb.45.1840.

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41

HIRASAWA, Noriyuki, Hirokazu OKAMOTO, and Kazumi DANJO. "Lactose as a Low Molecular Weight Carrier of Solid Dispersions for Carbamazepine and Ethenzamide." CHEMICAL & PHARMACEUTICAL BULLETIN 47, no. 3 (1999): 417–20. http://dx.doi.org/10.1248/cpb.47.417.

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42

Tong, Yao, Zhanzhong Wang, Entao Yang, et al. "Determination and correlation of solubility and solution thermodynamics of ethenzamide in different pure solvents." Fluid Phase Equilibria 427 (November 2016): 549–56. http://dx.doi.org/10.1016/j.fluid.2016.08.019.

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43

Acebedo-Martínez, Francisco, Carolina Alarcón-Payer, Lucía Rodríguez-Domingo, Alicia Domínguez-Martín, Jaime Gómez-Morales, and Duane Choquesillo-Lazarte. "Furosemide/Non-Steroidal Anti-Inflammatory Drug–Drug Pharmaceutical Solids: Novel Opportunities in Drug Formulation." Crystals 11, no. 11 (2021): 1339. http://dx.doi.org/10.3390/cryst11111339.

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The design of drug–drug multicomponent pharmaceutical solids is one the latest drug development approaches in the pharmaceutical industry. Its purpose is to modulate the physicochemical properties of active pharmaceutical ingredients (APIs), most of them already existing in the market, achieving improved bioavailability properties, especially on oral administration drugs. In this work, our efforts are focused on the mechanochemical synthesis and thorough solid-state characterization of two drug–drug cocrystals involving furosemide and two different non-steroidal anti-inflammatory drugs (NSAIDs

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44

Mary, Y. Sheena, Y. Shyma Mary, and Razieh Razavi. "Co-crystals of ethenzamide with 2-nitrobenzoic acid - Conformational analysis, MD simulations and DFT investigations." Journal of the Indian Chemical Society 99, no. 5 (2022): 100439. http://dx.doi.org/10.1016/j.jics.2022.100439.

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45

Jouyban, Abolghasem. "Comments on “Experimental measurement and thermodynamic modelling of ethenzamide solubility in three binary solvent systems”." Journal of Chemical Thermodynamics 163 (December 2021): 106594. http://dx.doi.org/10.1016/j.jct.2021.106594.

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46

Kozak, Agnieszka, Paulina H. Marek, and Edyta Pindelska. "Structural Characterization and Pharmaceutical Properties of Three Novel Cocrystals of Ethenzamide With Aliphatic Dicarboxylic Acids." Journal of Pharmaceutical Sciences 108, no. 4 (2019): 1476–85. http://dx.doi.org/10.1016/j.xphs.2018.10.060.

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47

Tong, Yao, Peng Zhang, Leping Dang, and Hongyuan Wei. "Monitoring of cocrystallization of ethenzamide–saccharin: Insight into kinetic process by in situ Raman spectroscopy." Chemical Engineering Research and Design 109 (May 2016): 249–57. http://dx.doi.org/10.1016/j.cherd.2016.01.032.

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48

Tong, Yao, Zhanzhong Wang, Entao Yang, Bochen Pan, Leping Dang, and Hongyuan Wei. "Insights into Cocrystal Polymorphic Transformation Mechanism of Ethenzamide–Saccharin: A Combined Experimental and Simulative Study." Crystal Growth & Design 16, no. 9 (2016): 5118–26. http://dx.doi.org/10.1021/acs.cgd.6b00688.

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49

Aitipamula, Srinivasulu, Pui Shan Chow, and Reginald B. H. Tan. "Polymorphs and Solvates of a Cocrystal Involving an Analgesic Drug, Ethenzamide, and 3,5-Dinitrobenzoic Acid." Crystal Growth & Design 10, no. 5 (2010): 2229–38. http://dx.doi.org/10.1021/cg9015178.

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50

Tong, Yao, Zhanzhong Wang, Leping Dang, and Hongyuan Wei. "Solid–liquid phase equilibrium and ternary phase diagrams of ethenzamide-saccharin cocrystals in different solvents." Fluid Phase Equilibria 419 (July 2016): 24–30. http://dx.doi.org/10.1016/j.fluid.2016.02.047.

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