A new pure paracetamol for direct compression: The orthorhombic form

Martino, Piera Di; Guyot-Hermann, A. M.; Conflant, P.; Drache, M.; Guyot, J. C.

doi:10.1016/0378-5173(95)04127-3

Cited by 195 publications

(151 citation statements)

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“…The exothermic peak at 73°C might be due to the recrystallization of glassy form of solidified acetaminophen melt, which was consistent with other reports. 4,6,9,10) However, the interpretations of the exothermic peak at 125°C were controversial, including habit transformation and solid state conversion from form II to form I, 8,10) although our thermal FT-IR microscopic results failed to support these explanations. From the above FT-IR spectral evidence, we regarded this exothermic peak at 125°C as a result of polymorphic phase transition from form III to form II, also consistent with Martino's study.…”

contrasting

confidence: 54%

“…4,6,10) This suggests that there was no physical stability problem of acetaminophen after compression of making a KBr disc. Three-dimensional plots of FT-IR spectra of acetaminophen on first-heating (A) and second-heating (B) with respect to the temperature are shown in Fig.…”

Section: Resultsmentioning

confidence: 98%

“…4a, a native acetaminophen (sample 1) showed an endothermic peak near 170°C with an enthalpy of 187 J/g, and should be confirmed as form I acetaminophen. 6,10) However, the DSC curve of the sample 2 indicated two exothermic peaks near 73°C (110 J/g) and 125°C (8 J/g), and one endothermic peak at 159°C (178 J/g), respectively (Fig. 4b).…”

mentioning

confidence: 99%

“…On the other hand, the orthorhombic acetaminophen not only has a sliding plane for good compression but also shows a faster dissolution rate than the monoclinic form. [6][7][8] Therefore, many studies have focused on how to prepare the orthorhombic form of acetaminophen. [8][9][10] An unstable third modification of acetaminophen (form III) has been found after different crystallization methods and the cooling rates, but the ambiguous explanations due to various differential scanning calorimetry (DSC) curves obtained have caused argument.…”

mentioning

confidence: 99%

“…1-4) Form I has poor binding and densification properties, 5,6) and is not suitable for direct compression into tablet. The preparation for monoclinic acetaminophen tablets therefore needs a series of time-and material consuming processes and excipients, and the size of the tablets cannot but be enlarged.…”

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confidence: 99%

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Transformation of Metastable Forms of Acetaminophen Studied by Thermal Fourier Transform Infrared (FT-IR) Microspectroscopy.

2002

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Acetaminophen is still worldwide used for analgesic and antipyretic therapy by millions of tablets and other dosage forms. Two polymorphs of acetaminophen have been published: form I is a monoclinic crystal and form II is an orthorhombic crystal. Form I (the usual form) is more stable at room temperature than form II.1-4) Form I has poor binding and densification properties, 5,6) and is not suitable for direct compression into tablet. The preparation for monoclinic acetaminophen tablets therefore needs a series of time-and material consuming processes and excipients, and the size of the tablets cannot but be enlarged. On the other hand, the orthorhombic acetaminophen not only has a sliding plane for good compression but also shows a faster dissolution rate than the monoclinic form. [6][7][8] Therefore, many studies have focused on how to prepare the orthorhombic form of acetaminophen. [8][9][10] An unstable third modification of acetaminophen (form III) has been found after different crystallization methods and the cooling rates, but the ambiguous explanations due to various differential scanning calorimetry (DSC) curves obtained have caused argument. [8][9][10][11] In the present study, a simple, quick and timesaving tool of Fourier transform infrared (FT-IR) microspectroscopy equipped with a micro hot stage (thermal FT-IR microscopic system) was used to readily and exactly explain the phase transition of metastable forms of acetaminophen by one-step process, as compared with different DSC thermograms of acetaminophen polymorphs prepared by different methods. ExperimentalMaterials Acetaminophen was of pharmaceutical grade, purchased from Seven Star Pharm. Co., Ltd. Taiwan, ROC. It was first recrystallized from aqueous solution, and then stored at 25°C, 75% relative humidity (RH) for further use. KBr crystal was of analytical IR grade, purchased from Jasco Co., Tokyo, Japan.Thermal FT-IR Microspectroscopic Study The acetaminophen powder was sandwiched between two KBr pieces by a hydraulic press to form a disc. This sample disc was directly put on a micro hot stage (DSC microscopy cell, FP 84, Mettler, Switzerland). The cell was then set on the stage of the microscope installed in the FT-IR microscopic spectrophotometer (Micro FTIR-200, Jasco, Tokyo, Japan) with an MCT detector. The system was operated in the transmission mode. The desired sample size for determination was selected and defined by means of an Aperture Through Optical System (ATOS) using microscope. The temperature of DSC microscopy cell was monitored with a central processor (FT80HT, Mettler, Switzerland). The heating rate of DSC assembly was controlled at 3°C/min in ambient conditions. The sample disc was previously equilibrated at the starting temperature (25°C) for about 3 min and then heated to 200°C. The thermal-responsive IR spectra were recorded with respect to the temperature. After the first heating process, the sample disc was cooled to 25°C and then re-heated from 25 to 200°C in the same conditions. Preparation and Determination of Diff...

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confidence: 54%

Section: Resultsmentioning

confidence: 98%

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confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Transformation of Metastable Forms of Acetaminophen Studied by Thermal Fourier Transform Infrared (FT-IR) Microspectroscopy.

2002

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Solid‐state Nuclear Magnetic Resonance of Polymorphic Materials

Vogt¹

2011

Encyclopedia of Analytical Chemistry

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Solid‐state nuclear magnetic resonance (SSNMR) spectroscopy is a powerful analytical technique for the analysis of polymorphs, which are molecules that exist in different crystalline phases. In this review, applications of SSNMR to polymorphism and related phenomena in a variety of chemical systems are discussed, including pharmaceuticals, food materials, explosives, dyes and pigments, biomolecules, inorganic materials, and organometallic compounds. The advantages of SSNMR are highlighted in relation to other analytical techniques, such as diffraction methods. The SSNMR techniques commonly used to analyze these systems and probe aspects of their polymorphic structure are reviewed, and illustrative examples from each class are given. In recent years, increasingly sophisticated SSNMR methods have been applied to the analysis of polymorphism, including 2‐D correlation methods, methods that measure chemical shift tensors, methods that extract quadrupolar parameters at high static field strengths, and computational methods that assist in interpreting and understanding the experimental data in relation to crystal structure. Multicomponent crystals including salts, solvates, and cocrystals also display polymorphism, and are often included with polymorphs in investigations of supramolecular chemistry and crystal engineering. The relationship between crystalline and amorphous materials is also discussed to emphasize the applicability of the analytical technique and the complementary information often obtained. Finally, the importance of SSNMR within multidisciplinary studies of polymorphism using other techniques is emphasized.

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Polymorphs

2017

Solid State Properties of Pharmaceutical Materials

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A new pure paracetamol for direct compression: The orthorhombic form

Cited by 195 publications

References 3 publications

Transformation of Metastable Forms of Acetaminophen Studied by Thermal Fourier Transform Infrared (FT-IR) Microspectroscopy.

Transformation of Metastable Forms of Acetaminophen Studied by Thermal Fourier Transform Infrared (FT-IR) Microspectroscopy.

Solid‐state Nuclear Magnetic Resonance of Polymorphic Materials

Polymorphs

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