Solvates and polymorphs of clindamycin phosphate: Structural, thermal stability and moisture stability studies

doi:10.1007/s11705-017-1624-4

Front. Chem. Sci. Eng.

2017, Vol. 11

Issue (2) : 220-230 https://doi.org/10.1007/s11705-017-1624-4

RESEARCH ARTICLE

Solvates and polymorphs of clindamycin phosphate: Structural, thermal stability and moisture stability studies

Junbo Gong^1,²(

), Dejiang Zhang^1,², Yuanyuan Ran^1,², Keke Zhang^1,², Shichao Du^1,²

¹. School of Chemical Engineering and Technology, State Key Laboratory of Chemical Engineering, Tianjin University, Tianjin 300072, China
². Collaborative Innovation Center of Chemical Seience and Engineering (Tianjin), Tianjin University, Tianjin 300072, China

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Abstract

Clindamycin phosphate (CP), an antibacterial agent, has been reported to form several solid-state forms. The crystal structures of two CP solvates, a dimethyl sulfoxide (DMSO) solvate and a methanol/water solvate (solvate V), have been determined by single crystal X-ray diffraction. The properties and transformations of these forms were characterized by powder X-ray diffraction, Single-crystal X-ray diffraction, differential scanning calorimetry, thermo gravimetric analysis, hot-stage microscopy, and dynamic vapor sorption. Very different hydrogen bonding networks exist among the host-host and host-solvent molecules in the two crystal structures, resulting in different moisture stabilities. The thermal stabilities of the two solvates upon heating and desolvation were also studied. When the temperature was above the boiling point of methanol, solvate V converted to a polymorphic phase after a one step desolvation process, whereas the desolvation temperature of the DMSO solvate was below the boiling point of DMSO. At the relative humidity above 43%, the DMSO solvate transformed to a hydrate at 25 °C. In contrast, solvate V did not transform at any of the humidities studied.

Keywords clindamycin phosphate solvate crystal structure thermal stability moisture stability

Corresponding Author(s): Junbo Gong

Just Accepted Date: 12 January 2017 Online First Date: 17 March 2017 Issue Date: 12 May 2017

Cite this article:

Junbo Gong,Dejiang Zhang,Yuanyuan Ran, et al. Solvates and polymorphs of clindamycin phosphate: Structural, thermal stability and moisture stability studies[J]. Front. Chem. Sci. Eng., 2017, 11(2): 220-230.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-017-1624-4
https://academic.hep.com.cn/fcse/EN/Y2017/V11/I2/220

Fig.1 Molecular structure of clindamycin phosphate

Tab.1 The different relative humidity value of saturated salt solution

Fig.2 PXRD patterns of CP solvates. (a) S_DMSO; (b) solvate V

Tab.2 Crystallographic data for CP S_DMSO and Solvate V

Fig.3 (a) Hydrogen bonds in S_DMSO crystal structure; (b) a unit cell of S_DMSO crystal

Fig.4 (a) The layered structure in S_DMSOcrystal; (b) hydrogen bonding networks and resulting construction of DMSO channels in the S_DMSO crystal structure. The blue lines indicated the hydrogen bonds

Tab.3 Hydrogen bond parameters for S_DMSO

Fig.5 (a) Hydrogen bonds in solvate V crystal structure; (b) a unit cell of solvate V crystal

Tab.4 Hydrogen bond parameters for solvate V

Fig.6 (a) DSC plots of S_DMSO and solvate V; (b) TGA plot of S_DMSO

Fig.7 HSM images showing the desolvation and melting of S_DMSO

Fig.8 Crystal packing of solvate V viewed along the c axis. Clindamycin phosphate molecules (blue) were shown as space filling models (van der Waals radius)

Fig.9 (a) S_DMSO sorption-desorption cycles performed at 25 °C; (b) PXRD patterns of S_DMSO under different RHs

Fig.10 (a) Channel formation in the host-DMSO assembly (along the b axis). The blue and red dashed lines represent hydrogen bonds; (b) space filling model with DMSO molecules removed (using van der Waals radius)

Fig.11 (a) Moisture sorption isotherm of solvate V performed at 25 °C; (b) PXRD patterns of solvate V following exposure to RH values ranging from 7% to 98%, each for 2 weeks at 25 °C

Fig.12 PXRD patterns of polymorph VI following exposure to RH values ranging from 7% to 98%, each for 1 week at 25 °C

Fig.13 Schematic representation of the moisture-induced solid-state transition between different forms of clindamycin phosphate

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