Polymorphism of Sulindac: Isolation and Characterization of a New Polymorph and Three New Solvates

Ilarduya, Conchita Tros de; Martı́n, Carmen; Goñi, M.; Martínez-Ohárriz, María Cristina

doi:10.1021/js9601748

Cited by 22 publications

(17 citation statements)

References 19 publications

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“…The polymorphism of flurbiprofen (FBP) and sulindac (SUL) has been studied for decades yielding three polymorphs of each drug 20–24. In the case of FBP, two polymorphs are stable at ambient conditions, while the other is reported to be stable only when crystallized between a cover slip and glass slide or in an aluminum pan 22.…”

Section: Introductionmentioning

confidence: 99%

“…Furthermore, only the crystal structure of FBP form I has been determined 25. Similarly, of the three SUL polymorphs, all of which are reported to be stable at ambient conditions,23, 24 the crystal structure of only form II has been elucidated 26. In this case, the structure determined is actually of the thermally less stable form II and the data are not of sufficient quality for accurately characterizing key intermolecular interactions.…”

Section: Introductionmentioning

confidence: 99%

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New form discovery for the analgesics flurbiprofen and sulindac facilitated by polymer‐induced heteronucleation

Grzesiak¹,

Matzger²

2007

Journal of Pharmaceutical Sciences

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The selection and discovery of new crystalline forms is a longstanding issue in solid-state chemistry of critical importance because of the effect molecular packing arrangement exerts on materials properties. Polymer-induced heteronucleation has recently been developed as a powerful approach to discover and control the production of crystal modifications based on the insoluble polymer heteronucleant added to the crystallization solution. The selective nucleation and discovery of new crystal forms of the well-studied pharmaceuticals flurbiprofen (FBP) and sulindac (SUL) has been achieved utilizing this approach. For the first time, FBP form III was produced in bulk quantities and its crystal structure was also determined. Furthermore, a novel 3:2 FBP:H 2 O phase was discovered that nucleates selectively from only a few polymers. Crystallization of SUL in the presence of insoluble polymers facilitated the growth of form I single crystals suitable for structure determination. Additionally, a new SUL polymorph (form IV) was discovered by this method. The crystal forms of FBP and SUL are characterized by Raman and FTIR spectroscopies, X-ray diffraction, and differential scanning calorimetry.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New form discovery for the analgesics flurbiprofen and sulindac facilitated by polymer‐induced heteronucleation

Grzesiak¹,

Matzger²

2007

Journal of Pharmaceutical Sciences

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“…The DSC thermogram of the as-received material shows a melting onset of 184.6 • C and a heat of fusion of 31 KJ/ mol, which is also consistent with values reported for Form II in literature. 17 In contrast to the well resolved XRPD pattern of the crystalline material, the meltquenched material shows a broad halo characteristic of amorphous materials. The DSC thermogram of the melt-quenched sample displayed a distinct T g with a calculated midpoint of 74.1 • C and an associated heat capacity change of 0.46 J/g/ • C.…”

Section: Resultsmentioning

confidence: 95%

“…Three anhydrous forms (Forms I-III) and three solvates of Sulindac have been reported in literature. 17 Forms I and II of Sulindac are reported to be enantiotropic with Form II being the room temperature stable form. The XRPD pattern of the as-received crystalline material conforms to Form II pattern reported in literature with prominent peaks at 9.8 • , 15.3 • , 21.5 • , and 29.3 • 2θ.…”

Section: Resultsmentioning

confidence: 99%

Manufacture and Performance Evaluation of a Stable Amorphous Complex of an Acidic Drug Molecule and Neusilin

Maclean

Medina

Daurio

et al. 2011

Journal of Pharmaceutical Sciences

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“…1) There are several useful reviews on the pharmaceutical applications of polymorphs, [2][3][4][5][6] and the study of polymorphism of newly developed compounds is important. A polymorphism is a solid material with at least two different molecular arrangements giving distinct crystal species.…”

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confidence: 99%

Characterization of Polymorphs of a Novel Quinolinone Derivative, TA-270 (4-Hydroxy-1-methyl-3-octyloxy-7-sinapinoylamino-2(1H)-quinolinone).

Kimura

Fukui

Takagaki

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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TA-270 (4-hydroxy-1-methyl-3-octyloxy-7-sinapinoylamino-2(1H)-quinolinone, Fig. 1) is a newly developed antiallergy compound. TA-270 inhibits the immediate-and late-airway responses, pulmonary inflammatory cell accumulation, and airway hypersensitiveness.1) There are several useful reviews on the pharmaceutical applications of polymorphs, [2][3][4][5][6] and the study of polymorphism of newly developed compounds is important. A polymorphism is a solid material with at least two different molecular arrangements giving distinct crystal species. There can be large differences in their physical properties and also differences in bioavailability. 7,8) Several techniques for solid state measurements have been reported in the study of polymorphs: microscopy, infrared (IR) spectroscopy, 9) differential scanning calorimetry (DSC), [10][11][12] powder X-ray diffractometry, 13,14) and solid state NMR spectroscopy. [15][16][17][18][19][20][21] In the present study, the characterization of various crystalline forms of TA-270 was examined as a preformulation study. To confirm the molecular state of the polymorphic forms, powder X-ray diffractometry, thermal analysis, IR spectroscopy and solid state 13 C-NMR spectroscopy were performed. The intrinsic dissolution rate of each form was analyzed based on the rotating disk method. In vivo studies were also performed using Male Cr:CD strain rats. ExperimentalMaterials TA-270 was synthesized by the synthetic department of Dainippon Ink and Chemicals, Inc. and the purity of the compound was above 99 %. The a, b and d polymorphic forms were prepared by recrystallization from acetonitrile, ethanol, and acetone, respectively. The amorphous form was prepared by milling the b-form with a vibrating mill (CMT MGF, TI-300). All other chemicals and solvents were of analytical reagent grade.Powder X-Ray Diffraction The powder X-ray diffraction pattern was measured with an X-ray diffractometer (Model RINT Ultima, Rigaku Denki). The conditions of measurement were as follows: target Cu, monochrometer graphite, voltage 40 kV and current 30 mA, with a scanning speed of 2°/min.Thermal Analysis DSC thermograms were obtained by a differential scanning calorimeter (Model DSC7, Perkin-Elmer). The measurements were made using an aluminum sample pan (sample weights were 6-10 mg) under a nitrogen atmosphere at a scanning speed of 5 or 20°C/min. Temperature scale was calibrated by an Indium standard.Thermogravimetry (TG) curves were obtained with a thermogravimeter (Model TGA7, Perkin-Elmer ).IR Spectroscopy IR spectra were obtained with a Fourier transform (FT)-IR spectrometer (Perkin Elmer Spectrum One) using a diffuse reflectance technique. 22)Dissolution Rate Measurement The intrinsic dissolution rate was determined according to the rotating disk method under the following conditions: 2%w/v Tween80-pH 8.0 phosphate buffer (37°C), stirring rate of 100 rpm. A disk (diameter: 8 mm) was prepared by compressing a 100 mg sample under a pressure of 196 MPa in a hydraulic press. It was confirmed by powder X-ray...

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Polymorphism of Sulindac: Isolation and Characterization of a New Polymorph and Three New Solvates

Cited by 22 publications

References 19 publications

New form discovery for the analgesics flurbiprofen and sulindac facilitated by polymer‐induced heteronucleation

New form discovery for the analgesics flurbiprofen and sulindac facilitated by polymer‐induced heteronucleation

Manufacture and Performance Evaluation of a Stable Amorphous Complex of an Acidic Drug Molecule and Neusilin

Characterization of Polymorphs of a Novel Quinolinone Derivative, TA-270 (4-Hydroxy-1-methyl-3-octyloxy-7-sinapinoylamino-2(1H)-quinolinone).

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