Thermal studies of furosemide–caffeine binary system that forms a cocrystal

Pal, Sharmistha; Roopa, B. N.; Abu, Khalid; Manjunath, S. Gajanan. M.; Nambiar, Sudhir

doi:10.1007/s10973-013-3031-5

Cited by 19 publications

(14 citation statements)

References 23 publications

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“…The melting of citric acid and urea is, in turn, followed by decomposition above 210°C, whereas melted p-aminobenzoic acid evaporates above 240°C. These data are consistent with those found in the literature [19,[34][35][36][37][38][39][40][41]. Sign of the DSC peaks: a, endothermic; b, exothermic; c, material safety data sheet provided by producers DSC as a screening tool for rapid co-crystal detection in binary mixtures of benzodiazepines……”

Section: Benzodiazepines and Co-formerssupporting

confidence: 90%

DSC as a screening tool for rapid co-crystal detection in binary mixtures of benzodiazepines with co-formers

Saganowska

Wesołowski

2017

J Therm Anal Calorim

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In recent years, co-crystals have been the subject of increasing interest within the pharmaceutical industry because these new solid forms of active pharmaceutical ingredients have the ability to enhance the bioavailability of poorly water-soluble drugs with a low dissolution rate. For this reason, it is crucial to prepare co-crystals of benzodiazepines, i.e. psychoactive drugs with a wide range of medical applications but classified as very slightly or practically insoluble in water. Thus, the objective of this research was to show to what extent the DSC method can be used as a screening tool for detection of cocrystal formation in binary physical mixtures of drugs and co-formers. To obtain potential co-crystals, eight benzodiazepines (diazepam, temazepam, oxazepam, lormetazepam, lorazepam, clonazepam, estazolam and chlordiazepoxide) were gently mixed in an agate mortar at 1:1 molar ratios with nine co-formers-succinic, glutaric, fumaric, citric and paminobenzoic acids, nicotinamide, saccharin, urea and caffeine, and heated under DSC conditions. A detailed comparison of the DSC scans of mixtures against scans of both ingredients in isolation indicates the occurrence of subtle physical changes in the samples. Thus, additional endothermic or exothermic peaks due to melting or crystallisation suggested the formation of potential co-crystals. To conclude, this study confirms that the DSC method can be used as a rapid screening tool for co-crystal detection. In this case, based on the DSC scans, 15 physical mixtures of benzodiazepines (clonazepam, diazepam, lorazepam, oxazepam and temazepam) with co-formers (citric, fumaric, glutaric, p-aminobenzoic and succinic acids, nicotinamide, saccharin and urea) have been selected as potential co-crystals for further detailed study.

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Section: Benzodiazepines and Co-formerssupporting

confidence: 90%

DSC as a screening tool for rapid co-crystal detection in binary mixtures of benzodiazepines with co-formers

Saganowska

Wesołowski

2017

J Therm Anal Calorim

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“…9) On the other hand, the hydrogen bonding interaction occurs between COOH and sulfonamide S=O of FUR and pyridinium N and NH 2 of NIC, respectively. 11) The crystal structure of FUR-UREA has not been entirely clarified. There might be no interaction between the sulfonamide of FUR and NH 2 of urea via hydrogen bonding, because FUR-UREA did not exhibit a peak shift toward shorter wavelengths from the absorption maximum.…”

Section: Characterization Of Fur Cocrystalsmentioning

confidence: 99%

“…8) FUR was cocrystallized with various coformers such as caffeine (CAF), urea (UREA), p-aminobenzoic acid, nicotinamide (NIC), etc. [9][10][11][12] Goud et al demonstrated that the solubility of FUR-CAF was approximately 6-fold higher than that of FUR. 9) FUR is unstable under light, as described above.…”

Section: Introductionmentioning

confidence: 99%

Improving the Solid-State Photostability of Furosemide by Its Cocrystal Formation

et al. 2019

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The photostability of three types of furosemide (FUR) cocrystal (FUR-caffeine, FUR-urea, and FURnicotinamide cocrystals) was studied under irradiation with a D65 fluorescent lamp. The coloration of the FUR-urea pellets was significantly faster than that of the intact FUR, whereas the coloration of FUR-nicotinamide was suppressed compared with that of intact FUR and the other cocrystals. In the case of FUR-urea, the chemical degradation of FUR increased by approximately 6.6% after irradiation for 90 d. On the other hand, FUR-nicotinamide showed better chemical stability, with only 1.3% of FUR degraded, which was significantly lower than the other cocrystals. The FUR-urea pellets showed a UV-Visible absorption spectrum similar to that of intact FUR, while the absorption range of FUR-nicotinamide shifted to a shorter wavelength. The light sensitivity of FUR-nicotinamide was improved because of the much lower emission of the D65 fluorescent lamp in the absorption range of the cocrystal.

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“…55 The fact reported that cocrystals could be formed during the phase transition of the lowtemperature stable polymorph of furosemide if coformer is available in close contact with the transforming component suggesting increased mass transfer rate can trigger cocrystal formation. 56 In the summary polymorphic transformation of cocrystals has the ability to alter various pharmaceutical aspects related to an API, including but not limited to solubility, dissolution, bioavailability, and stability. It was also reported in the literature that processing parameters could lead to polymorphic transformations of cocrystals while some metastable polymorphic forms are converted to the stable form after storage.…”

Section: Polymorphism and Cocrystalsmentioning

confidence: 99%

Pharmaceutical Cocrystals: Regulatory and Strategic Aspects, Design and Development

Gadade¹,

Pekamwar²

2016

Adv Pharm Bull

122

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Thermal studies of furosemide–caffeine binary system that forms a cocrystal

Cited by 19 publications

References 23 publications

DSC as a screening tool for rapid co-crystal detection in binary mixtures of benzodiazepines with co-formers

DSC as a screening tool for rapid co-crystal detection in binary mixtures of benzodiazepines with co-formers

Improving the Solid-State Photostability of Furosemide by Its Cocrystal Formation

Pharmaceutical Cocrystals: Regulatory and Strategic Aspects, Design and Development

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