Crystal structure of (<i>S</i>)-5-chloro-<i>N</i>-({2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl}methyl)thiophene-2-carboxamide

Shen, Jie; Tang, Guping; Hu, Xiurong

doi:10.1107/s2056989017017819

Cited by 6 publications

(7 citation statements)

References 9 publications

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“…X-ray structure determination revealed the molecular structure of RIV with a hydrogen-bonded network (Figure ). The crystal structure parameters are in good agreement with the recently published crystal structure of RIV by Shen and co-workers . Further discussion on crystallographic features of RIV can be found in the Supporting Information.…”

Section: Resultssupporting

confidence: 88%

“…The crystal structure parameters are in good agreement with the recently published crystal structure of RIV by Shen and coworkers. 38 Further discussion on crystallographic features of RIV can be found in the Supporting Information. RIV-MAL also crystallized in the triclinic crystal system with the noncentrosymmetric, P1 space group and the structure consists of four molecules of RIV along with two molecules of MAL (2:1 stoichiometry) (Figure 3).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Molecular Basis of Water Sorption Behavior of Rivaroxaban-Malonic Acid Cocrystal

et al. 2019

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The present study aims to investigate the molecular basis of water sorption behavior of rivaroxaban-malonic acid cocrystal (RIV-MAL). It was hypothesized, that the amount of water sorbed by a crystalline solid is governed by the surface molecular environment of different crystal facets and their relative abundance to crystal surface. Water sorption behavior was measured using a dynamic vapor sorption analyzer. The surface molecular environment of different crystal facets and their relative contribution were determined using single crystal structure evaluation and face indexation analysis, respectively. The surface area-normalized water sorption for rivaroxaban (RIV), malonic acid (MAL), and RIV-MAL at 90% RH/25 °C was 0.28, 92.6, and 11.1% w/w, respectively. The crystal surface of MAL had a larger contribution (58.7%) of hydrophilic (Hphi) functional groups and showed the “highest” water sorption (92.6% w/w). On the contrary, RIV had a larger surface contribution (65.2%) of hydrophobic (Hpho) functional groups, and the smaller contribution (34.8%) of Hphi+Hpho groups exhibited the “lowest” water sorption (0.28% w/w). The “intermediate” water sorption (11.1% w/w) by RIV-MAL, as compared to RIV, was ascribed to the increased surface contribution of Hphi+Hpho groups (from 34.8 to 42.1%) and reduced hydrophobic surface contribution (from 65.2 to 57.9%). However, the significantly higher water gained (∼39-fold) by the cocrystal as compared to RIV, despite the nominal change in the surface contributions, was further attributed to the relatively stronger hydrogen bonding interactions between the surface-exposed carboxyl groups and water molecules. The study highlights that the amount of water sorbed by the cocrystal is governed by the surface molecular environment and additionally by the strength of hydrogen bonding. This investigation has implications on designing materials with a desired moisture-sorption property.

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Section: Resultssupporting

confidence: 88%

Section: ■ Results and Discussionmentioning

confidence: 99%

Molecular Basis of Water Sorption Behavior of Rivaroxaban-Malonic Acid Cocrystal

et al. 2019

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“…S8 and S9). The crystal structures of RXB, 46 RXB-malonic acid 9,10 and RXB-oxalic acid 47 also revealed their dimeric structure similar to Fig. 10a (ESI † Fig.…”

Section: Prediction Of Intermolecular Associations Using Dft Studiesmentioning

confidence: 56%

Rivaroxaban eutectics with improved solubility, dissolution rates, bioavailability and stability

et al. 2023

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“…The patent, while heralding the commercial viability and industrial advantages of this crystalline form, points towards an ongoing scientific journey. 15 15,16 B -X-ray diffraction profile of rivaroxaban (cambridge crystallographic data center deposition number 1810879 using Mercury software, version 3.7) similar to form I available in patent number WO2015/111076A2. 15,16…”

Section: Crystal Forms and Enhanced Selectivitymentioning

confidence: 99%

Unlocking the polymorphic odyssey of Rivaroxaban: a journey of pharmaceutical innovation

Bonilha Dezena,

Pires Rosa

2024

PPIJ

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The field of pharmaceutical science is a dynamic landscape driven by the pursuit of enhanced drug formulations and improved therapeutic outcomes. One remarkable journey within this domain is the polymorphism odyssey of rivaroxaban, a distinguished anticoagulant inhibitor targeting blood coagulation factor Xa. Rivaroxaban plays a key role in the prevention and treatment of thromboembolic disorders, including myocardial infarction, stroke, and deep venous thromboses. Its intricate crystal structures and diverse solid-state forms, each imparting unique properties affecting solubility, bioavailability, and stability, illuminate the challenges, breakthroughs, and relentless pursuit of superior drug performance in the pharmaceutical development of rivaroxaban. This work not only reflects the scientific commitment to enhancing therapeutic efficacy but also underscores the dynamic interplay between chemical innovation and clinical application in drug development.

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Crystal structure of (S)-5-chloro-N-({2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl}methyl)thiophene-2-carboxamide

Cited by 6 publications

References 9 publications

Molecular Basis of Water Sorption Behavior of Rivaroxaban-Malonic Acid Cocrystal

Molecular Basis of Water Sorption Behavior of Rivaroxaban-Malonic Acid Cocrystal

Rivaroxaban eutectics with improved solubility, dissolution rates, bioavailability and stability

Unlocking the polymorphic odyssey of Rivaroxaban: a journey of pharmaceutical innovation

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