Cocristales farmacéuticos de pirazinamida con dos ácidos carboxílicos: cristalización y caracterización cristalográfica estructural
El trabajo cuenta con la caracterización de los dos cocristales encontrados.
- Autores:
-
Sánchez Sánchez, Cristian Camilo
- Tipo de recurso:
- Trabajo de grado de pregrado
- Fecha de publicación:
- 2022
- Institución:
- Universidad de los Andes
- Repositorio:
- Séneca: repositorio Uniandes
- Idioma:
- spa
- OAI Identifier:
- oai:repositorio.uniandes.edu.co:1992/69155
- Acceso en línea:
- http://hdl.handle.net/1992/69155
- Palabra clave:
- Cocristales farmacéuticos
Cristalografía
Rayos X
Caracterización
Cristalización
Química
- Rights
- openAccess
- License
- Atribución-NoComercial-CompartirIgual 4.0 Internacional
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Cocristales farmacéuticos de pirazinamida con dos ácidos carboxílicos: cristalización y caracterización cristalográfica estructural |
| title |
Cocristales farmacéuticos de pirazinamida con dos ácidos carboxílicos: cristalización y caracterización cristalográfica estructural |
| spellingShingle |
Cocristales farmacéuticos de pirazinamida con dos ácidos carboxílicos: cristalización y caracterización cristalográfica estructural Cocristales farmacéuticos Cristalografía Rayos X Caracterización Cristalización Química |
| title_short |
Cocristales farmacéuticos de pirazinamida con dos ácidos carboxílicos: cristalización y caracterización cristalográfica estructural |
| title_full |
Cocristales farmacéuticos de pirazinamida con dos ácidos carboxílicos: cristalización y caracterización cristalográfica estructural |
| title_fullStr |
Cocristales farmacéuticos de pirazinamida con dos ácidos carboxílicos: cristalización y caracterización cristalográfica estructural |
| title_full_unstemmed |
Cocristales farmacéuticos de pirazinamida con dos ácidos carboxílicos: cristalización y caracterización cristalográfica estructural |
| title_sort |
Cocristales farmacéuticos de pirazinamida con dos ácidos carboxílicos: cristalización y caracterización cristalográfica estructural |
| dc.creator.fl_str_mv |
Sánchez Sánchez, Cristian Camilo |
| dc.contributor.advisor.none.fl_str_mv |
Macías López, Mario Alberto |
| dc.contributor.author.none.fl_str_mv |
Sánchez Sánchez, Cristian Camilo |
| dc.contributor.jury.none.fl_str_mv |
Hurtado Belalcazar, John Jady Zapata Rivera, Jhon Enrique Miscione, Gian Pietro |
| dc.contributor.researchgroup.es_CO.fl_str_mv |
Grupo de investigación: Cristalografía y Química de Materiales |
| dc.subject.keyword.none.fl_str_mv |
Cocristales farmacéuticos Cristalografía Rayos X Caracterización Cristalización |
| topic |
Cocristales farmacéuticos Cristalografía Rayos X Caracterización Cristalización Química |
| dc.subject.themes.es_CO.fl_str_mv |
Química |
| description |
El trabajo cuenta con la caracterización de los dos cocristales encontrados. |
| publishDate |
2022 |
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2022-06-01 |
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2023-08-03T14:09:03Z |
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2023-08-03T14:09:03Z |
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Trabajo de grado - Pregrado |
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Jaskolski M, Dauter Z, Wlodawer A. A brief history of macromolecular crystallography, illustrated by a family tree and its Nobel fruits. FEBS J. 2014 Sep;281(18):3985-4009. doi: 10.1111/febs.12796. Epub 2014 Apr 17. PMID: 24698025; PMCID: PMC6309182 Schwarzenbach, Dieter. (2013). History of Crystallography Steurer, W. (2007). What is a crystal?: Introductory remarks to an ongoing discussion. Zeitschrift Für Kristallographie, 222(6). doi:10.1524/zkri.2007.222.6.308 Lifshitz, Ron. (2007). What is a crystal?. Zeitschrift Fur Kristallographie. 222. 313-317. 10.1524/zkri.2007.222.6.313 Yu, L., & Reutzel-Edens, S. M. (2003). CRYSTALLIZATION | Basic Principles. Encyclopedia of Food Sciences and Nutrition, 1697-1702. doi:10.1016/b0-12-227055-x/00313-8 Sauter, Claude & Lorber, Bernard & McPherson, Alexander & Giegé, Richard. (2012). Crystallization - General Methods Prasad, M. R., Deb, P. K., Chandrasekaran, B., Maheshwari, R., & Tekade, R. K. (2018). Basics of Crystallization Process Applied in Drug Exploration. Dosage Form Design Parameters, 67-103. doi:10.1016/b978-0-12-814421-3.00003-8 Chen, Y., Ma, P., & Gui, S. (2014). Cubic and Hexagonal Liquid Crystals as Drug Delivery Systems. BioMed Research International, 2014, 1-12. doi:10.1155/2014/815981 Aitipamula, S., Banerjee, R., Bansal, A. K., Biradha, K., Cheney, M. L., Choudhury, A. R., ... Zaworotko, M. J. (2012). Polymorphs, Salts, and Cocrystals: What's in a Name? Crystal Growth & Design, 12(5), 2147-2152. doi:10.1021/cg3002948 Yadav A., Shete A., Dabke A., Kulkarni P., Sakhare S. Co-crystals: A novel approach to modify physicochemical properties of active pharmaceutical ingredients. Indian J. Pharm. Sci. 2009;71:359. doi: 10.4103/0250-474X.5728 Kumar, Sandeep & Nanda, Arun. (2017). Pharmaceutical Cocrystals: An Overview. Indian Journal of Pharmaceutical Sciences. 79. 10.4172/pharmaceutical-sciences.1000302 Dutt B, Choudhary M, Budhwar V. Cocrystallization: An innovative route toward better medication. J Rep Pharma Sci 2020;9:256-70 Childs, S. L., & Zaworotko, M. J. (Eds.). (2009). The Reemergence of Cocrystals: The Crystal Clear Writing Is on the WallIntroduction to Virtual Special Issue on Pharmaceutical Cocrystals. Crystal Growth & Design, 9(10), 4208-4211. doi:10.1021/cg901002y Ascierto, P.A., Marincola, F.M. Combination therapy: the next opportunity and challenge of medicine. J Transl Med 9, 115 (2011). https://doi.org/10.1186/1479-5876-9-115 McMahon, J. A., Bis, J. A., Vishweshwar, P., Shattock, T. R., McLaughlin, O. L., & Zaworotko, M. J. (2005). Crystal engineering of the composition of pharmaceutical phases. 3. Primary amide supramolecular heterosynthons and their role in the design of pharmaceutical co-crystals. Zeitschrift Für Kristallographie - Crystalline Materials, 220(4). doi:10.1524/zkri.220.4.340.61624 Grobelny, P., Mukherjee, A., & Desiraju, G. R. (2011). Drug-drug co-crystals: Temperature dependent proton mobility in the molecular complex of isoniazid with 4-aminosalicylic acid. CrystEngComm, 13(13), 4358. doi:10.1039/c0ce00842g Cherukuvada, S., & Nangia, A. (2012). Fast dissolving eutectic compositions of two antitubercular drugs. CrystEngComm, 14(7), 2579. doi:10.1039/c2ce06391c Adalder, T. K., Sankolli, R., & Dastidar, P. (2012). Homo- or Heterosynthon? A Crystallographic Study on a Series of New Cocrystals Derived from Pyrazinecarboxamide and Various Carboxylic Acids Equipped with Additional Hydrogen Bonding Sites. Crystal Growth & Design, 12(5), 2533-2542. doi:10.1021/cg300140w Luo, Y.-H., & Sun, B.-W. (2013). Pharmaceutical Co-Crystals of Pyrazinecarboxamide (PZA) with Various Carboxylic Acids: Crystallography, Hirshfeld Surfaces, and Dissolution Study. Crystal Growth & Design, 13(5), 2098-2106. doi:10.1021/cg400167w Lou, M., Mao, S.-H., Luo, Y.-H., Zhao, P., & Sun, B.-W. (2013). Synthesis, co-crystal structure and characterization of pyrazinamide with m-hydroxybenzoic acid, p-hydroxybenzoic acid and 3,4-dihydroxy benzolic acid. Research on Chemical Intermediates, 41(5), 2939-2951. doi:10.1007/s11164-013-1402-y Wang, J.-R., Ye, C., Zhu, B., Zhou, C., & Mei, X. (2015). Pharmaceutical cocrystals of the anti tuberculosis drug pyrazinamide with dicarboxylic and tricarboxylic acids. CrystEngComm, 17(4), 747-752. doi:10.1039/c4ce02044h Abourahma, H., Shah, D. D., Melendez, J., Johnson, E. J., & Holman, K. T. (2015). A Tale of Two Stoichiometrically Diverse Cocrystals. Crystal Growth & Design, 15(7), 3101-3104. doi:10.1021/acs.cgd.5b00357 Thorat, S. H., Sahu, S. K., & Gonnade, R. G. (2015). Crystal structures of the pyrazinamide-p-aminobenzoic acid (1/1) cocrystal and the transamidation reaction product 4-(pyrazine-2- carboxamido)benzoic acid in the molten state. Acta Crystallographica Section C Structural Chemistry, 71(11), 1010-1016. doi:10.1107/s2053229615019828 Kulla, H., Greiser, S., Benemann, S., Rademann, K., & Emmerling, F. (2016). In Situ Investigation of a Self-Accelerated Cocrystal Formation by Grinding Pyrazinamide with Oxalic Acid. Molecules, 21(7), 917. doi:10.3390/molecules21070917 Jarzembska, K. N., Hoser, A. A., Varughese, S., Kaminski, R., Malinska, M., Stachowicz, M., ... Wozniak, K. (2017). Structural and Energetic Analysis of Molecular Assemblies in a Series of Nicotinamide and Pyrazinamide Cocrystals with Dihydroxybenzoic Acids. Crystal Growth & Design, 17(9), 4918-4931. doi:10.1021/acs.cgd.7b00868 Sarmah, K. K., Rajbongshi, T., Bhowmick, S., & Thakuria, R. (2017). First-line antituberculosis drug, pyrazinamide, its pharmaceutically relevant cocrystals and a salt. Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials, 73(5), 1007-1016. doi:10.1107/s2052520617011477 Liu, F., Song, Y., Liu, Y.-N., Li, Y.-T., Wu, Z.-Y., & Yan, C.-W. (2018). Drug-Bridge-Drug Ternary Cocrystallization Strategy for Antituberculosis Drugs Combination. Crystal Growth & Design, 18(3), 1283-1286. doi:10.1021/acs.cgd.7b01738 Bommaka, M. K., Mannava, M. K. C., Suresh, K., gunnam, anilkumar, & Nangia, A. (2018). Entacapone: Improving Aqueous Solubility, Diffusion Permeability and Cocrystal Stability with Theophylline. Crystal Growth & Design. doi:10.1021/acs.cgd.8b00921 Rajbongshi, T., Sarmah, K. K., Sarkar, A., Ganduri, R., Cherukuvada, S., Thakur, T. S., & Thakuria, R. (2018). Preparation of Pyrazinamide Eutectics Vs. Cocrystals Based on Supramolecular Synthon Variations. Crystal Growth & Design. doi:10.1021/acs.cgd.8b00878 Kulla, H., Michalchuk, A. A. L., & Emmerling, F. (2019). Manipulating the Dynamics of Mechanochemical Ternary Co-Crystal Formation. Chemical Communications. doi:10.1039/c9cc03034d Kulla, H., Becker, C., Michalchuk, A. A. L., Linberg, K., Paulus, B., & Emmerling, F. (2019). Tuning the apparent stability of polymorphic cocrystals through mechanochemistry. Crystal Growth & Design. doi:10.1021/acs.cgd.9b01158 32. Who.int. 2021. Tuberculosis. [online] Available at: https://www.who.int/es/newsroom/fact-sheets/detail/tuberculosis Tuberculosis - OPS/OMS | Organización Panamericana de la Salud. https://www.paho.org/es/temas/tuberculosis Churchyard, G., Kim, P., Shah, N. S., Rustomjee, R., Gandhi, N., Mathema, B., Dowdy, D., Kasmar, A., & Cardenas, V. (2017). What We Know About Tuberculosis Transmission: An Overview. The Journal of infectious diseases, 216(suppl_6), S629-S635. https://doi.org/10.1093/infdis/jix362 History of Tuberculosis. (1994). Tuberculosis, 13-24. doi:10.1128/9781555818357.ch2 Manual operativo de la OMS sobre la tuberculosis. Módulo 4: Tratamiento. Tratamiento de la tuberculosis farmacorresistente. Washington, D.C.: Organización Panamericana de la Salud; 2022. Licencia: CC BY-NC-SA 3.0 IGO. https://doi. org/10.37774/9789275325575 Nahid, P., Dorman, S. E., Alipanah, N., Barry, P. M., Brozek, J. L., Cattamanchi, A., Chaisson, L. H., Chaisson, R. E., Daley, C. L., Grzemska, M., Higashi, J. M., Ho, C. S., Hopewell, P. C., Keshavjee, S. A., Lienhardt, C., Menzies, R., Merrifield, C., Narita, M., O'Brien, R., Peloquin, C. A., ... Vernon, A. (2016). Official American Thoracic Society/Centers for Disease Control and Prevention/Infectious Diseases Society of America Clinical Practice Guidelines: Treatment of Drug-Susceptible Tuberculosis. Clinical infectious diseases : an official publication of the Infectious Diseases Society of America, 63(7), e147-e195. https://doi.org/10.1093/cid/ciw376 Harmon, R. C. (2007). Pyrazinamide. xPharm: The Comprehensive Pharmacology Reference, 1-5. doi:10.1016/b978-008055232-3.62492-4 Cherukuvada, S., Thakuria, R., & Nangia, A. (2010). Pyrazinamide Polymorphs: Relative Stability and Vibrational Spectroscopy. Crystal Growth & Design, 10(9), 3931-3941. doi:10.1021/cg1004424 Takaki, Y., Sasada, Y., & Watanabé, T. (1960). The crystal structure of alpha-pyrazinamide. Acta Crystallographica, 13(9), 693-702. doi:10.1107/s0365110x60001680 Wang, D., Yang, Z., Zhu, B., Mei, X., & Luo, X. (2020). Machine-Learning-Guided Cocrystal Prediction Based on Large Data Base. Crystal Growth & Design, 20(10), 6610-6621. doi:10.1021/acs.cgd.0c00767 |
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Atribución-NoComercial-CompartirIgual 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-sa/4.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2Macías López, Mario Albertovirtual::3744-1Sánchez Sánchez, Cristian Camilo08cd8272-a207-4bf9-b8b9-6f88f50fea5e600Hurtado Belalcazar, John JadyZapata Rivera, Jhon EnriqueMiscione, Gian PietroGrupo de investigación: Cristalografía y Química de Materiales2023-08-03T14:09:03Z2023-08-03T14:09:03Z2022-06-01http://hdl.handle.net/1992/69155instname:Universidad de los Andesreponame:Repositorio Institucional Sénecarepourl:https://repositorio.uniandes.edu.co/El trabajo cuenta con la caracterización de los dos cocristales encontrados.Dos nuevos cocristales farmacéuticos: 1. PZA-ATE (pirazinamida-ácido tereftálico), 2. PZA-ATR (pirazinamida-ácido trimésico) fueron sintetizados y caracterizados mediante difracción de rayos-X de monocristal (DRXM). Como resultado se encontró que la PZA formó un cocristal 1:1 con ATE, mientras con ATR formó un cocristal 2:1. Este trabajo muestra, describe y analiza la estructura molecular y supramolecular de ambas estructuras cristalinas no reportadas previamenteQuímicoPregrado32 páginasapplication/pdfspaUniversidad de los AndesQuímicaFacultad de CienciasDepartamento de QuímicaCocristales farmacéuticos de pirazinamida con dos ácidos carboxílicos: cristalización y caracterización cristalográfica estructuralTrabajo de grado - Pregradoinfo:eu-repo/semantics/bachelorThesisinfo:eu-repo/semantics/acceptedVersionhttp://purl.org/coar/resource_type/c_7a1fTexthttp://purl.org/redcol/resource_type/TPCocristales farmacéuticosCristalografíaRayos XCaracterizaciónCristalizaciónQuímicaJaskolski M, Dauter Z, Wlodawer A. A brief history of macromolecular crystallography, illustrated by a family tree and its Nobel fruits. FEBS J. 2014 Sep;281(18):3985-4009. doi: 10.1111/febs.12796. Epub 2014 Apr 17. PMID: 24698025; PMCID: PMC6309182Schwarzenbach, Dieter. (2013). History of CrystallographySteurer, W. (2007). What is a crystal?: Introductory remarks to an ongoing discussion. Zeitschrift Für Kristallographie, 222(6). doi:10.1524/zkri.2007.222.6.308Lifshitz, Ron. (2007). What is a crystal?. Zeitschrift Fur Kristallographie. 222. 313-317. 10.1524/zkri.2007.222.6.313Yu, L., & Reutzel-Edens, S. M. (2003). CRYSTALLIZATION | Basic Principles. Encyclopedia of Food Sciences and Nutrition, 1697-1702. doi:10.1016/b0-12-227055-x/00313-8Sauter, Claude & Lorber, Bernard & McPherson, Alexander & Giegé, Richard. (2012). Crystallization - General MethodsPrasad, M. R., Deb, P. K., Chandrasekaran, B., Maheshwari, R., & Tekade, R. K. (2018). Basics of Crystallization Process Applied in Drug Exploration. Dosage Form Design Parameters, 67-103. doi:10.1016/b978-0-12-814421-3.00003-8Chen, Y., Ma, P., & Gui, S. (2014). Cubic and Hexagonal Liquid Crystals as Drug Delivery Systems. BioMed Research International, 2014, 1-12. doi:10.1155/2014/815981Aitipamula, S., Banerjee, R., Bansal, A. K., Biradha, K., Cheney, M. L., Choudhury, A. R., ... Zaworotko, M. J. (2012). Polymorphs, Salts, and Cocrystals: What's in a Name? Crystal Growth & Design, 12(5), 2147-2152. doi:10.1021/cg3002948Yadav A., Shete A., Dabke A., Kulkarni P., Sakhare S. Co-crystals: A novel approach to modify physicochemical properties of active pharmaceutical ingredients. Indian J. Pharm. Sci. 2009;71:359. doi: 10.4103/0250-474X.5728Kumar, Sandeep & Nanda, Arun. (2017). Pharmaceutical Cocrystals: An Overview. Indian Journal of Pharmaceutical Sciences. 79. 10.4172/pharmaceutical-sciences.1000302Dutt B, Choudhary M, Budhwar V. Cocrystallization: An innovative route toward better medication. J Rep Pharma Sci 2020;9:256-70Childs, S. L., & Zaworotko, M. J. (Eds.). (2009). The Reemergence of Cocrystals: The Crystal Clear Writing Is on the WallIntroduction to Virtual Special Issue on Pharmaceutical Cocrystals. Crystal Growth & Design, 9(10), 4208-4211. doi:10.1021/cg901002yAscierto, P.A., Marincola, F.M. Combination therapy: the next opportunity and challenge of medicine. J Transl Med 9, 115 (2011). https://doi.org/10.1186/1479-5876-9-115McMahon, J. A., Bis, J. A., Vishweshwar, P., Shattock, T. R., McLaughlin, O. L., & Zaworotko, M. J. (2005). Crystal engineering of the composition of pharmaceutical phases. 3. Primary amide supramolecular heterosynthons and their role in the design of pharmaceutical co-crystals. Zeitschrift Für Kristallographie - Crystalline Materials, 220(4). doi:10.1524/zkri.220.4.340.61624Grobelny, P., Mukherjee, A., & Desiraju, G. R. (2011). Drug-drug co-crystals: Temperature dependent proton mobility in the molecular complex of isoniazid with 4-aminosalicylic acid. CrystEngComm, 13(13), 4358. doi:10.1039/c0ce00842gCherukuvada, S., & Nangia, A. (2012). Fast dissolving eutectic compositions of two antitubercular drugs. CrystEngComm, 14(7), 2579. doi:10.1039/c2ce06391cAdalder, T. K., Sankolli, R., & Dastidar, P. (2012). Homo- or Heterosynthon? A Crystallographic Study on a Series of New Cocrystals Derived from Pyrazinecarboxamide and Various Carboxylic Acids Equipped with Additional Hydrogen Bonding Sites. Crystal Growth & Design, 12(5), 2533-2542. doi:10.1021/cg300140wLuo, Y.-H., & Sun, B.-W. (2013). Pharmaceutical Co-Crystals of Pyrazinecarboxamide (PZA) with Various Carboxylic Acids: Crystallography, Hirshfeld Surfaces, and Dissolution Study. Crystal Growth & Design, 13(5), 2098-2106. doi:10.1021/cg400167wLou, M., Mao, S.-H., Luo, Y.-H., Zhao, P., & Sun, B.-W. (2013). Synthesis, co-crystal structure and characterization of pyrazinamide with m-hydroxybenzoic acid, p-hydroxybenzoic acid and 3,4-dihydroxy benzolic acid. 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