Rapid Structure Determination of Ranitidine Hydrochloride API in Two Crystal Forms Using Microcrystal Electron Diffraction
The solid-state properties of drug candidates play a crucial role in their selection. Quality control of active pharmaceutical ingredients (APIs) based on their structural information involves ensuring a consistent crystal form and controlling water and residual solvent contents. However, traditiona...
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| Published in | Chemical & pharmaceutical bulletin Vol. 72; no. 5; pp. 471 - 474 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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Japan
The Pharmaceutical Society of Japan
2024
Japan Science and Technology Agency |
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| Abstract | The solid-state properties of drug candidates play a crucial role in their selection. Quality control of active pharmaceutical ingredients (APIs) based on their structural information involves ensuring a consistent crystal form and controlling water and residual solvent contents. However, traditional crystallographic techniques have limitations and require high-quality single crystals for structural analysis. Microcrystal electron diffraction (microED) overcomes these challenges by analyzing difficult-to-crystallize or small-quantity samples, making it valuable for efficient drug development. In this study, microED analysis was able to rapidly determine the configuration of two crystal forms (Forms 1, 2) of the API ranitidine hydrochloride. The structures obtained with microED are consistent with previous structures determined by X-ray diffraction, indicating microED is a useful tool for rapidly analyzing molecular structures in drug development and materials science research. |
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| AbstractList | The solid-state properties of drug candidates play a crucial role in their selection. Quality control of active pharmaceutical ingredients (APIs) based on their structural information involves ensuring a consistent crystal form and controlling water and residual solvent contents. However, traditional crystallographic techniques have limitations and require high-quality single crystals for structural analysis. Microcrystal electron diffraction (microED) overcomes these challenges by analyzing difficult-to-crystallize or small-quantity samples, making it valuable for efficient drug development. In this study, microED analysis was able to rapidly determine the configuration of two crystal forms (Forms 1, 2) of the API ranitidine hydrochloride. The structures obtained with microED are consistent with previous structures determined by X-ray diffraction, indicating microED is a useful tool for rapidly analyzing molecular structures in drug development and materials science research. The solid-state properties of drug candidates play a crucial role in their selection. Quality control of active pharmaceutical ingredients (APIs) based on their structural information involves ensuring a consistent crystal form and controlling water and residual solvent contents. However, traditional crystallographic techniques have limitations and require high-quality single crystals for structural analysis. Microcrystal electron diffraction (microED) overcomes these challenges by analyzing difficult-to-crystallize or small-quantity samples, making it valuable for efficient drug development. In this study, microED analysis was able to rapidly determine the configuration of two crystal forms (Forms 1, 2) of the API ranitidine hydrochloride. The structures obtained with microED are consistent with previous structures determined by X-ray diffraction, indicating microED is a useful tool for rapidly analyzing molecular structures in drug development and materials science research.The solid-state properties of drug candidates play a crucial role in their selection. Quality control of active pharmaceutical ingredients (APIs) based on their structural information involves ensuring a consistent crystal form and controlling water and residual solvent contents. However, traditional crystallographic techniques have limitations and require high-quality single crystals for structural analysis. Microcrystal electron diffraction (microED) overcomes these challenges by analyzing difficult-to-crystallize or small-quantity samples, making it valuable for efficient drug development. In this study, microED analysis was able to rapidly determine the configuration of two crystal forms (Forms 1, 2) of the API ranitidine hydrochloride. The structures obtained with microED are consistent with previous structures determined by X-ray diffraction, indicating microED is a useful tool for rapidly analyzing molecular structures in drug development and materials science research. |
| ArticleNumber | c23-00745 |
| Author | Yokoo, Hidetomo Demizu, Yosuke Uchiyama, Nahoko Yamamoto, Eiichi Aoyama, Yoshitaka Matsumoto, Takashi |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/38749738$$D View this record in MEDLINE/PubMed |
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| References_xml | – reference: 16) Kolb U., Gorelik T., Kübel C., Otten M. T., Hubert D., Ultramicroscopy, 107, 507–513 (2007). – reference: 4) Palatinus L., Brázda P., Boullay P., Perez O., Klementová M., Petit S., Eigner V., Zaarour M., Mintova S., Science, 355, 166–169 (2017). – reference: 17) Kolb U., Gorelik T., Otten M. T., Ultramicroscopy, 108, 763–772 (2008). – reference: 13) Ito S., White F. J., Okunishi E., Aoyama Y., Yamano A., Sato H., Ferrara J. D., Jasnowski M., Meyer M., CrystEngComm, 23, 8622–8630 (2021). – reference: 28) Mirmehrabi M., Rohani S., Murthy K., Radatus B., J. Cryst. Growth, 260, 517–526 (2004). – reference: 5) Jones C. G., Martynowycz M. W., Hattne J., Fulton T. J., Stoltz B. M., Rodriguez J. A., Nelson H. M., Gonen T., ACS Cent. Sci., 4, 1587–1592 (2018). – reference: 9) Gruene T., Wennmacher J. T. C., Zaubitzer C., Holstein J. J., Heidler J., Fecteau-Lefebvre A., De Carlo S., Müller E., Goldie K. N., Regeni I., Li T., Santiso-Quinones G., Steinfeld G., Handschin S., van Genderen E., van Bokhoven J. A., Clever G. H., Pantelic R., Angew. Chem. Int. Ed., 57, 16313–16317 (2018). – reference: 10) Brázda P., Palatinus L., Babor M., Science, 364, 667–669 (2019). – reference: 22) Nannenga B. L., Struct. Dyn., 7, 014304 (2020). – reference: 18) Kolb U., Mugnaioli E., Gorelik T., Cryst. Res. Technol., 46, 542–554 (2011). – reference: 12) Woollam G. R., Das P. P., Mugnaioli E., Andrusenko I., Galanis A. S., van de Streek J., Nicolopoulos S., Gemmi M., Wagner T., CrystEngComm, 22, 7490–7499 (2020). – reference: 25) Yamamoto E., Takeda Y., Ando D., Koide T., Amano Y., Miyazaki S., Miyazaki T., Izutsu K. I., Kanazawa H., Goda Y., Int. J. Pharm., 605, 120834 (2021). – reference: 19) Shi D., Nannenga B. L., Iadanza M. G., Gonen T., eLife, 2, e01345 (2013). – reference: 31) Hempel A., Camerman N., Mastropaolo D., Camerman A., Acta Crystallogr. C, 56, 1048–1049 (2000). – reference: 20) Sawaya M. R., Rodriguez J., Cascio D., Collazo M. J., Shi D., Reyes F. E., Hattne J., Gonen T., Eisenberg D. S., Proc. Natl. Acad. Sci. U.S.A., 113, 11232–11236 (2016). – reference: 21) Hattne J., Reyes F. E., Nannenga B. L., Shi D., de la Cruz M. J., Leslie A. G., Gonen T., Acta Crystallogr. A Found. Adv., 71, 353–360 (2015). – reference: 3) Nederlof I., van Genderen E., Li Y. W., Abrahams J. P., Acta Crystallogr. D Biol. Crystallogr., 69, 1223–1230 (2013). – reference: 14) Sekharan S., Liu X., Yang Z., Liu X., Deng L., Ruan S., Abramov Y., Sun G., Li S., Zhou T., Shi B., Zeng Q., Zeng Q., Chang C., Jin Y., Shi X., RSC Adv., 11, 17408–17412 (2021). – reference: 7) Gorelik T. E., van de Streek J., Kilbinger A. F., Brunklaus G., Kolb U., Acta Crystallogr. B, 68, 171–181 (2012). – reference: 24) Yokoo H., Tanaka S., Yamamoto E., Tsuji G., Demizu Y., Uchiyama N., Chem. Pharm. Bull., 71, 58–63 (2023). – reference: 11) Andrusenko I., Hamilton V., Mugnaioli E., Lanza A., Hall C., Potticary J., Hall S. R., Gemmi M., Angew. Chem. Int. Ed., 58, 10919–10922 (2019). – reference: 15) Karothu D. P., Alhaddad Z., Göb C. R., Schürmann C. J., Bücker R., Naumov P., Angew. Chem. Int. Ed., 62, e202303761 (2023). – reference: 23) Shi D., Nannenga B. L., de la Cruz M. J., Liu J., Sawtelle S., Calero G., Reyes F. E., Hattne J., Gonen T., Nat. Protoc., 11, 895–904 (2016). – reference: 8) van Genderen E., Clabbers M. T., Das P. P., Stewart A., Nederlof I., Barentsen K. C., Portillo Q., Pannu N. S., Nicolopoulos S., Gruene T., Abrahams J. P., Acta Crystallogr. A Found. Adv., 72, 236–242 (2016). – reference: 26) Guerrieri P., Salameh A. K., Taylor L. S., Pharm. Res., 24, 147–156 (2007). – reference: 27) Chieng N., Zujovic Z., Bowmaker G., Rades T., Saville D., Int. J. Pharm., 327, 36–44 (2006). – reference: 2) Nannenga B. L., Gonen T., Nat. 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| SubjectTerms | Active control active pharmaceutical ingredient crystal polymorphism Crystallization Crystallography Crystals Drug development Electron diffraction Electrons microcrystal electron diffraction Microcrystals Molecular Structure Quality control Ranitidine Ranitidine - chemistry Ranitidine hydrochloride Single crystals Structural analysis X-ray diffraction |
| Title | Rapid Structure Determination of Ranitidine Hydrochloride API in Two Crystal Forms Using Microcrystal Electron Diffraction |
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