Hostname: page-component-74656f9884-8r8nv Total loading time: 0 Render date: 2026-11-07T03:51:10.167Z Has data issue: false hasContentIssue false
  • English
  • Français

X-ray powder diffraction data for rivaroxaban, C19H18ClN3O5S

Published online by Cambridge University Press:  16 December 2021

Hua Shao ,
Zhen Wang ,
Shu Xie  and
Bin Liu Open the ORCID record for Bin Liu [Opens in a new window]
Hua Shao
Affiliation:
Medical College, Yangzhou University, Yangzhou 225009, China Department of Vasculocardiology, Yangzhou Friendship Hospital, Yangzhou 225009, China
Zhen Wang
Affiliation:
Department of Vasculocardiology, Yangzhou Friendship Hospital, Yangzhou 225009, China
Shu Xie
Affiliation:
Department of Vasculocardiology, Yangzhou Friendship Hospital, Yangzhou 225009, China
Bin Liu*
Affiliation:
Department of Vasculocardiology, Yangzhou Friendship Hospital, Yangzhou 225009, China
*
a)Author to whom correspondence should be addressed. Electronic mail: lb710823@sina.cn

Abstract

X-ray powder diffraction data, unit-cell parameters, and space group for rivaroxaban, C19H18ClN3O5S, are reported [a = 9.010(3) Å, b = 10.986(6) Å, c = 11.230(1) Å, α = 63.439(5)°, β = 74.355(4)°, γ = 78.133(3)°, unit-cell volume V = 952.87 Å3, Z = 2, ρcal = 1.519 g cm−3, and space group P1]. All measured lines were indexed and are consistent with the P1 space group. No detectable impurities were observed.

Keywords

rivaroxabanfactor Xa inhibitorX-ray powder diffraction

Information

Type
Data Report
Information
Powder Diffraction , Volume 37 , Issue 1 , March 2022 , pp. 40 - 42
Check for updates
Copyright
Copyright © The Author(s), 2021. Published by Cambridge University Press on behalf of International Centre for Diffraction Data

I. INTRODUCTION

Rivaroxaban (Figure 1), a novel oral direct factor Xa inhibitor, has been widely used for nonvalvular atrial fibrillation (NVAF) and deep venous thrombosis or venous embolism (Akao et al., Reference Akao, Yasuda, Kaikita, Ako, Matoba, Nakamura, Miyauchi, Hagiwara, Kimura, Hirayama, Matsui and Ogawa2021). It can inhibit the formation of thrombin by inhibiting factor Xa activity and ultimately inhibit thrombus formation and enlargement (Ajmal et al., Reference Ajmal, Friedman, Sipra and Lassar2021).

Figure 1.

Molecular diagram of rivaroxaban.

The single crystallographic data of rivaroxaban [a = 9.0184 (6) Å, b = 10.9980 (8) Å, c = 11.2386 (8) Å, α = 63.426 (2)°, β = 74.414 (3)°, γ = 78.144 (2)°, unit-cell volume V = 955.56 (12) Å3, Z = 2, ρ cal = 1.515 g cm−3, and space group P1] had been deposited with the Cambridge Crystallographic Data Center (CCDC) with a supplementary publication number of CCDC-1810879 (Shen et al., Reference Shen, Tang and Hu2017). To date, the detailed X-ray powder diffraction (PXRD) data for rivaroxaban have not been reported.

II. EXPERIMENTAL

A. Sample preparation

The sample was purchased from Energy Chemical (Shanghai, People's Republic of China). The melting point and measured density of rivaroxaban are 227–228 °C and 1.491 g cm−3, respectively. Recrystallization of rivaroxaban at room temperature was successful using methanol as a solvent. Then, the crystals were dried, smashed, screened through 75 μm mesh size, and pressed flat to a zero background plate.

B. Diffraction data collection and reduction

XRD measurement was performed at room temperature using a Bruker D8 Advance diffractometer (Bruker, AXS, Germany) with a LynxEye array detector and CuKα radiation (generator setting: 40 kV and 40 mA). The diffraction data were collected over the angular range from 5° to 50° 2θ with a step size of 0.019757° 2θ and a counting time of 37 ms/step. Some peaks in the diffraction pattern display asymmetry which is possibly because of stacking faults (Langford and Louër, Reference Langford and Louër1991).

The software package Material Studio 8.0 (Accelrys Co., Ltd., CA, USA) was used to process the data. The PXRD pattern was pre-treated by subtracting the background, smoothing, and stripping off the Kα 2 component. Peaks were located in the diffraction pattern using automated peak searching. Automatic indexing results were obtained by X-cell method (Neumann, Reference Neumann2003). The indexing results were then refined using Pawley (R wp = 6.51%) (Pawley, Reference Pawley1981), which involves assigning the Miller indices (h, k, l) to each observed peak in the experimental PXRD pattern. Line shift correction was turned on during the cell parameter refinement. All measured lines in the raw data were indexed. The method of determination of intensity was peak height above background.

III. RESULTS

Pawley refinement results confirmed that rivaroxaban is triclinic with space group P1 and unit-cell parameters: a = 9.010(3) Å, b = 10.986(6) Å, c = 11.230(1) Å, α = 63.439(5)°, β = 74.355(4)°, γ = 78.133(3)°, unit-cell volume V = 952.87 Å3, Z = 2, ρ cal = 1.519 g cm−3. The values of 2θ obs, d obs, I obs, h, k, l, 2θ cal, d cal, Δ2θ are listed in Table I. The results are in good agreement with the single-crystal data and the deviations of the unit-cell parameters and unit-cell volume were between 0.02% and 0.28%. The comparison of PXRD pattern (raw data file deposited with ICDD) with the simulated pattern is shown in Figure 2.

Figure 2.

X-ray powder diffraction pattern of rivaroxaban using CuKα radiation (black solid line) and the simulated pattern of the crystal structure (green dash line).

TABLE I.

Indexed X-ray powder diffraction data for rivaroxaban.

The d-values were calculated using CuKα 1radiation (λ = 1.5405981 Å).

IV. DEPOSITED DATA

The rivaroxaban, the raw data file has been deposited with ICDD. You may request this data from ICDD at .

References

Ajmal, M., Friedman, J., Sipra, Q. U. A. R., and Lassar, T. (2021). “Rivaroxaban: expanded role in cardiovascular disease management – a literature review,” Cardiovasc. Ther. 2021, 8886210.CrossRefGoogle ScholarPubMed
Akao, M., Yasuda, S., Kaikita, K., Ako, J., Matoba, T., Nakamura, M., Miyauchi, K., Hagiwara, N., Kimura, K., Hirayama, A., Matsui, K., and Ogawa, H. (2021). “Rivaroxaban monotherapy versus combination therapy according to patient risk of stroke and bleeding in atrial fibrillation and stable coronary disease: AFIRE trial subanalysis,” Am. Heart J. 236, 59–68.CrossRefGoogle ScholarPubMed
Langford, J. I. and Louër, D. (1991). “High-resolution powder diffraction studies of copper(II) oxide,” J. Appl. Crystallogr. 24, 149–155.CrossRefGoogle Scholar
Neumann, M. A. (2003). “X-cell: a novel indexing algorithm for routine tasks and difficult cases,” J. Appl. Crystallogr. 36, 356–365.CrossRefGoogle Scholar
Pawley, G. S. (1981). “Unit-cell refinement from powder diffraction scans,” J. Appl. Crystallogr. 14(6), 357–361.CrossRefGoogle Scholar
Shen, J., Tang, G. P., and Hu, X. R. (2017). CCDC 1810879: Experimental Crystal Structure Determination.Google Scholar
Figure 0

Figure 1. Molecular diagram of rivaroxaban.

Figure 1

Figure 2. X-ray powder diffraction pattern of rivaroxaban using CuKα radiation (black solid line) and the simulated pattern of the crystal structure (green dash line).

Figure 2

TABLE I. Indexed X-ray powder diffraction data for rivaroxaban.