Insight into the Formation of Cocrystal and Salt of Tenoxicam from the Isomer and Conformation
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials
2.2. Methods
2.2.1. Preparation
2.2.2. Crystallization
2.3. Powder X-ray Diffraction (PXRD) Analysis
2.4. Single-Crystal X-ray Diffraction (SXRD) Analysis
2.5. Differential Scanning Calorimetry (DSC) Analysis
2.6. Infrared Spectroscopy (IR) Analysis
2.7. Raman Analysis
2.8. Theoretical Computation
2.9. Dissolution Measurements
3. Results and Discussion
3.1. Prediction of Interaction Sites
3.2. Single-Crystal X-ray Diffraction (SXRD) Analysis
3.3. Powder X-ray Diffraction (PXRD) Analysis
3.4. Infrared Spectroscopy (IR) Analysis
3.5. Raman Analysis
3.6. Differential Scanning Calorimetry (DSC) Analysis
3.7. Lattice Energy Analysis
3.8. Energy Decomposition Analysis (EDA)
3.9. Dissolution Measurement Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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CCF | Melting Point | Cocrystal Melting Point | pKa i Value | ΔpKa Value | Conformation of TNX |
---|---|---|---|---|---|
Glycolic acid (GLA) | 77.1 | 137.2 | 3.74 | 0.76 | Unknown |
4-Hydroxybenzoic acid (HBA) | 215.4 | 205.2 | 4.57 | 0.07 | Unknown |
α-Ketoglutaric acid (KLA) | 114.5 | 139.3 | 2.38 | 2.12 | Unknown |
Succinic acid (SNA) | 187.6 | 194 | 4.24 | 0.26 | Unknown |
Maleic acid (MLA) | 144.1 | 164.2 | 2.39 | 2.11 | Unknown |
Malonic acid (MNA) | 134.9 | 154 | 2.92 | 2.11 | Unknown |
Oxalic acid (OLA) | 191.7 | 203.6 | 1.38 | 1.58 | Unknown |
Saccharin (SCR) | 228.1 | 237.1 | 1.60 | 3.12 | Unknown |
Benzoic acid (BZA) | 122 | 185 | 4.20 | 1.49 | A |
Salicylic acid (SCA) | 159 | 200 | 3.01 | 0.30 | A |
Pyrocatechol (PRC) | 105 | 174 | 9.50 | 5.00 | A |
Resorcinol (RSC) | 110 | 190 | 9.45 | 4.95 | A |
Pyrogallol (PRG) | 131 | 180 | 9.28 | 4.78 | A |
Piperazine (PPZ) | 106 | 190 | 9.55 | 5.05 | B |
Hydrochloric acid (HCA) | — | 198 | −8 | 12.50 | B |
Methanesulfonic acid (MSA) | — | 209 | 1.75 | 2.75 | B |
p-Aminosalicylic acid (PAS) | 143.4 | 200.5 | 3.58 | 0.92 | A |
3,5-Dinitrobenzoic acid (DNB) | 205.9 | 209.3 | 2.77 | 1.73 | A |
2,6-Dihydroxybenzoic acid (DHB) | 169.3 | 206.4 | 1.30 | 3.20 | B |
TNX-PAS | TNX-DNB | TNX-DHB | |
---|---|---|---|
Formula | C13H11N3O4S2∙C7H7NO3 | C13H11N3O4S2∙C7H4N2O6 | C13H11N3O4S2∙C7H6O4 |
Description | flake | flake | flake |
Crystal system | monoclinic | triclinic | monoclinic |
Space group | P 21 | P | C 2/c |
Unit cell parameters (Å, °) | 9.220 (1) | 9.578 (1) | 21.516 (1) |
20.215 (1) | 10.721 (1) | 7.731 (1) | |
11.617 (1) | 11.617 (1) | 26.440 (1) | |
90 | 93.248 (3) | 90 | |
97.98 (1) | 107.587 (3) | 104.070 (10) | |
90 | 99.406 (2) | 90 | |
Volume (Å3) | 2144.65 (2) | 1114.75 (6) | 4266.37 (11) |
Z | 4 | 2 | 2 |
Density (g/cm3) | 1.519 | 1.637 | 1.530 |
Theta range for data collection | 3.84~72.14 | 4.01~71.55 | 3.42~72.16 |
Independent reflections | 7115 | 4187 | 4166 |
Reflections with I > 2σ(I) | 6192 | 3814 | 3694 |
R (I > 2σI) | R = 0.052 | R = 0.0404 | R = 0.0571 |
wR2 = 0.147 | wR2 = 0.1146 | wR2 = 0.1599 | |
Goodness-of-fit on F2 | 1.066 | 1.086 | 1.025 |
Completeness | 99.3 | 97.6 | 99.7 |
Deposition number | 2174287 | 2174286 | 2174285 |
Cocrystal/Salt | D–H…A | D…A (Å) | ∠DHA (°) |
---|---|---|---|
TNX-PAS | N2-H2…O1 | 2.607 | 140.28 |
N3-H3…O4 | 2.651 | 131.79 | |
N3-H3…O8 a | 2.894 | 139.58 | |
N1A-H1AB…O3 | 3.017 | 152.46 | |
O1A-H1A…O1 b | 2.572 | 160.00 | |
O3A-H3AA…O2A | 2.624 | 137.63 | |
TNX-DNB | N2-H2…O1 | 2.637 | 138.40 |
N3-H3…O4 (intra-) | 2.585 | 133.03 | |
N3-H3…O4 c (inter-) | 2.991 | 135.57 | |
O2D-H2D…O1 | 2.572 | 166.51 | |
TNX-DHB | N2-H2…O5 | 3.018 | 168.02 |
N3-H3A…O6 | 2.593 | 157.48 | |
O1-H1…O4 (intra-) | 2.559 | 142.82 | |
O1-H1…O4 d (inter-) | 2.886 | 122.41 | |
O7-H7…O6 | 2.529 | 146.91 | |
O8-H8…O5 | 2.568 | 147.81 |
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Xie, Y.; Yuan, P.; Heng, T.; Du, L.; An, Q.; Zhang, B.; Zhang, L.; Yang, D.; Du, G.; Lu, Y. Insight into the Formation of Cocrystal and Salt of Tenoxicam from the Isomer and Conformation. Pharmaceutics 2022, 14, 1968. https://doi.org/10.3390/pharmaceutics14091968
Xie Y, Yuan P, Heng T, Du L, An Q, Zhang B, Zhang L, Yang D, Du G, Lu Y. Insight into the Formation of Cocrystal and Salt of Tenoxicam from the Isomer and Conformation. Pharmaceutics. 2022; 14(9):1968. https://doi.org/10.3390/pharmaceutics14091968
Chicago/Turabian StyleXie, Yifei, Penghui Yuan, Tianyu Heng, Lida Du, Qi An, Baoxi Zhang, Li Zhang, Dezhi Yang, Guanhua Du, and Yang Lu. 2022. "Insight into the Formation of Cocrystal and Salt of Tenoxicam from the Isomer and Conformation" Pharmaceutics 14, no. 9: 1968. https://doi.org/10.3390/pharmaceutics14091968