Thermal behavior of orthorhombic polymorphs I and II of spironolactone

Espeau, Philippe; Nicolaı̈, Béatrice; Céolin, R.; Perrin, Μ.; Zaske, L.; Giovannini, J.; Leveiller, F.

doi:10.1007/s10973-007-8390-3

Cited by 11 publications

(13 citation statements)

References 2 publications

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“…For comparison with the melting data from the literature (Table 2), DSC measurements with 15 separate samples of form II were carried out (Table 3) demonstrating that the present sample of form II melts at 479.6 ± 0.6 K with a melting enthalpy of Δ II→L H = 54.0 ± 1.5 J g , respectively, in reference (Espeau et al, 2007). Form I was obtained from the Sanofi batch by evaporating an ethanol solution and its transformation behavior is represented by curve 3 in Fig.…”

Section: Calorimetric Datamentioning

confidence: 91%

“…The dimorphic system involving the orthorhombic forms of spironolactone, form I (Dideberg and Dupont, 1972) and form II (Agafonov et al, 1989), appear to exhibit a difference of more than 70 degrees in their melting temperatures, making it therefore an exceptionally uncommon case of crystalline polymorphism (Espeau et al, 2007). Form I melts and recrystallizes into form II in the temperature interval of 373-393 K. Form II, however, only melts at 480-483 K.…”

Section: The Exceptional Difference Between the Melting Points Of Thementioning

confidence: 99%

“…In 2003, high resolution X-ray powder diffraction experiments as a function of temperature demonstrated that form II exhibits no structural change up to its fusion, whereas form I transforms into form II in the 373-398 K temperature interval (Liebenberg et al, 2003). In 2007, a I → II transformation was observed with an onset in the 373-393 temperature interval and with a liquid as an intermediate phase, which was interpreted as a melting recrystallization (Espeau et al, 2007). Summing over the complete endo-exothermic effect resulted in a value of 0 ± 2 J g −1 for the enthalpy of the I → II transition at the temperature of fusion of form I leaving the relative enthalpy ranking between the two phases undetermined (Espeau et al, 2007).…”

Section: U N C O R R E C T E D P R O O Fmentioning

confidence: 99%

“…In 2007, a I → II transformation was observed with an onset in the 373-393 temperature interval and with a liquid as an intermediate phase, which was interpreted as a melting recrystallization (Espeau et al, 2007). Summing over the complete endo-exothermic effect resulted in a value of 0 ± 2 J g −1 for the enthalpy of the I → II transition at the temperature of fusion of form I leaving the relative enthalpy ranking between the two phases undetermined (Espeau et al, 2007). The melting enthalpy of form II, Δ II→L H = 55 J g −1 at 480 K (onset), was found to be close to previous values.…”

Section: U N C O R R E C T E D P R O O Fmentioning

confidence: 99%

“…The melting enthalpy of form II, Δ II→L H = 55 J g −1 at 480 K (onset), was found to be close to previous values. In addition, specific volumes of forms I, v I , and II, v II , were determined as a function of temperature in the range from room temperature up to their respective melting points (Espeau et al, 2007). At 300 K, those equations lead to the specific volumes v I (300 K) = 0.78942 cm 3 g −1 and v II (300 K) = 0.80099 cm 3 g −1 , which…”

Section: U N C O R R E C T E D P R O O Fmentioning

confidence: 99%

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Polymorphism of spironolactone: An unprecedented case of monotropy turning to enantiotropy with a huge difference in the melting temperatures

Rietveld

Lloveras

Céolin

et al. 2018

International Journal of Pharmaceutics

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Spironolactone form I melts at about 70 degrees lower than form II, which is very unusual for two co-existing polymorphs. The phase relationships involving this unprecedented case of dimorphism have been investigated by constructing a topological pressure-temperature phase diagram. The transition from polymorph I to polymorph II is unambiguously exothermic while it is accompanied with an increase in the specific volume. This indicates that the dP/dT slope of the I-II equilibrium curve is negative. The convergence of the melting equilibrium lines at high pressure lead to a topological P-T diagram in which polymorph I possesses a stable phase region at high pressure. Thus, forms I and II are monotropically related at ordinary pressure and turn to an enantiotropic relationship at high pressure. Given that polymorph I is the densest form, it negates the rule of thumb that the densest form is also the most stable form at room temperature, similar to the case of paracetamol.

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Section: Calorimetric Datamentioning

confidence: 91%

Section: The Exceptional Difference Between the Melting Points Of Thementioning

confidence: 99%

Section: U N C O R R E C T E D P R O O Fmentioning

confidence: 99%

Section: U N C O R R E C T E D P R O O Fmentioning

confidence: 99%

Section: U N C O R R E C T E D P R O O Fmentioning

confidence: 99%

See 3 more Smart Citations

Polymorphism of spironolactone: An unprecedented case of monotropy turning to enantiotropy with a huge difference in the melting temperatures

Rietveld

Lloveras

Céolin

et al. 2018

International Journal of Pharmaceutics

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Thermal investigation of relaxations of interacting and non-interacting amorphous solid dispersions

Péter-Haraszti,

Záhonyi,

Farkas

et al. 2024

J Therm Anal Calorim

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In the present research, thermal investigation of amorphous solid dispersions (ASDs) was performed in order to compare their relaxation transitions. Two different active pharmaceutical ingredients (APIs), namely naproxen (NAP) and spironolactone (SPIR), were used as model drugs and combined with polyvinylpyrrolidone vinyl acetate (PVPVA64) copolymer to form stable ASDs. The reason for the API selection was their different interacting potentials based on the presence (in the case of NAP) and the lack of H-bond donor group (in the case of SPIR). Determination of both Tg and sub-Tg transitions suggested that ASDs containing NAP and PVPVA64 are ‘interacting’ systems with respect to the H-bonding. Besides, temperature-dependent Raman spectroscopic experiments confirmed that the naphthalene ring of the NAP has a significant role in the sub-Tg relaxations. In contrast, SPIR-PVPVA64 systems proved to be ‘non-interacting’ ASDs according to the MDSC, TSDC, and Raman measurements. This study highlights that the combination of the results of different thermoanalytical investigations with spectroscopic methods helps to understand the molecular background of the relaxations in ASDs and thus contributes to the conscious design of stable amorphous pharmaceuticals in the early stage of development.

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Spironolactone nanocrystals for oral administration: Different pharmacokinetic performances induced by stabilizers

Guo

et al. 2016

Colloids and Surfaces B: Biointerfaces

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Thermal behavior of orthorhombic polymorphs I and II of spironolactone

Cited by 11 publications

References 2 publications

Polymorphism of spironolactone: An unprecedented case of monotropy turning to enantiotropy with a huge difference in the melting temperatures

Polymorphism of spironolactone: An unprecedented case of monotropy turning to enantiotropy with a huge difference in the melting temperatures

Thermal investigation of relaxations of interacting and non-interacting amorphous solid dispersions

Spironolactone nanocrystals for oral administration: Different pharmacokinetic performances induced by stabilizers

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