Study of the polymorphic behaviour of some local anesthetic drugs

Giron, D.; Draghi, M.; Goldbronn, C.; Pfeffer, Sabine; Piéchon, Philippe

doi:10.1007/bf01996777

Cited by 34 publications

(17 citation statements)

References 6 publications

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“…For tetracaine, a single melting endotherm was observed at 42.93°C in the first heating cycle, but there were two melting endotherms observed at 38.79 and 42.85°C in the second heating cycle. Tetracaine has no polymorphic form, as reported by Giron et al (39). Thus, the first melting endotherm (at 38.79°C) in the second heating cycle may be due to the formation of a metastable state of tetracaine, which is known to cause a decrease in the tetracaine melting point (40,41).…”

Section: Modulated Temperature Differential Scanning Calorimetrymentioning

confidence: 65%

Characterization and Comparison of Lidocaine-Tetracaine and Lidocaine-Camphor Eutectic Mixtures Based on Their Crystallization and Hydrogen-Bonding Abilities

et al. 2014

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Abstract. Eutectic mixtures formed between active pharmaceutical ingredients and/or excipients provide vast scope for pharmaceutical applications. This study aimed at the exploration of the crystallization abilities of two eutectic mixtures (EM) i.e., lidocaine-tetracaine and lidocaine-camphor (1:1 w/w). Thermogravimetric analysis (TGA) for degradation behavior whereas modulated temperature differential scanning calorimetry (MTDSC) set in first heating, cooling, and second heating cycles, was used to qualitatively analyze the complex exothermic and endothermic thermal transitions. Raman microspectroscopy characterized vibrational information specific to chemical bonds. Prepared EMs were left at room temperature for 24 h to visually examine their crystallization potentials. The degradation of lidocaine, tetracaine, camphor, lidocaine-tetracaine EM, and lidocaine-camphor EM began at 196.56, 163.82, 76.86, 146.01, and 42.72°C, respectively, which indicated that eutectic mixtures are less thermostable compared to their individual components. The MTDSC showed crystallization peaks for lidocaine, tetracaine, and camphor at 31.86, 29.36, and 174.02°C, respectively (n=3). When studying the eutectic mixture, no crystallization peak was observed in the lidocaine-tetracaine EM, but a lidocaine-camphor EM crystallization peak was present at 18.81°C. Crystallization occurred in lidocaine-camphor EM after being kept at room temperature for 24 h, but not in lidocaine-tetracaine EM. Certain peak shifts were observed in Raman spectra which indicated possible interactions of eutectic mixture components, when a eutectic mixture was formed. We found that if the components forming a eutectic mixture have crystallization peaks close to each other and have sufficient hydrogen-bonding capability, then their eutectic mixture is least likely to crystallize out (as seen in lidocaine-tetracaine EM) or vice versa (lidocainecamphor EM).

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Section: Modulated Temperature Differential Scanning Calorimetrymentioning

confidence: 65%

Characterization and Comparison of Lidocaine-Tetracaine and Lidocaine-Camphor Eutectic Mixtures Based on Their Crystallization and Hydrogen-Bonding Abilities

et al. 2014

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“…Many hydrates of drug substances have been reported, for instance, carbamazepine, 11) theophylline, 12) tetracaine hydrochloride, 13) levofloxacin, 14) and diclofenac acid salts. 15) Among them, the hydrated form exists in several possible hydration states.…”

mentioning

confidence: 99%

Water Vapor Adsorption Behavior of Sodium Deoxycholate Anhydrous Forms

Ono

Anzai

Tozuka

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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During pharmaceutical development processes, various investigations of physicochemical properties of a drug substance are conducted in order to guarantee the efficacy and the stability of pharmaceutical products. It is well known that the physicochemical properties of drug substances are changed by influence of water vapor under high and low relative humidity conditions. 2-4)A compound holding stoichiometric solvent molecule incorporated within the crystal lattice is designated a solvate. In particular, when the solvent is water, the compound is termed a hydrate, which is the most common solvate of drug substances.5) Because the investigation of manufacturing and formulation processes are conducted with particular attention to the behavior of drug substance hydrate, the existence of the hydrate state has a major impact on the drug development process.6) Moreover, the reduction in bioavailability may occur as the solubility of hydrate in general is lower than that of anhydrous form. 7,8) There are many studies in which the behavior of the crystal water molecule is influenced by relative humidity.9,10) A compound tends to incorporate a water molecule in the crystal structure at high relative humidities, while a hydrate may release the water molecule from the crystal at low relative humidities. It is therefore very important that the effect of relative humidity on the interconversion between the hydrate and anhydrous forms are investigated.Studies of the process of hydration and dehydration are of significance in order to predict the stability of the drug substance. Many hydrated compounds are stabilized by formation of hydrogen bonding networks between water and the drug substance molecule. A hydrated crystal is easily broken by heating and also upon storage at low relative humidities, leading to possible transformation into the anhydrous form by crystal lattice rearrangement. As a result, the drug substance may form the metastable state.Many hydrates of drug substances have been reported, for instance, carbamazepine, 11) theophylline, 12) tetracaine hydrochloride, 13) levofloxacin, 14) and diclofenac acid salts. 15)Among them, the hydrated form exists in several possible hydration states. Tetracaine hydrochloride has hemi-, mono-, and tetrahydrate states, nafagrel hydrochloride has hemi-and monohydrate states, and norfloxacin has sesqui-and pentahydrate states. 16)Sodium deoxycholate (NaDC) containing steroid skeleton is a kind of cholic acid salts. It is known that NaDC forms a micelle, 17) gel, 18) and complex 19) with drugs. It is a white powder used as a supportive solubilizing agent in pharmaceutical formulation. D'Archivio et al. suggested the possibility that NaDC was stabilized by the formation of a tetrahydrate helix structure of NaDC with the four water molecules held rigid by the formation of ion-ion, ion-dipole interactions and hydrogen bonding. 20) Vold et al. presumed the existence of NaDC octahydrate by the investigation of the solubility curve of NaDC.21) However, their findings could not sufficie...

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“…Double heating without TG measurement or cooling of the BupiHCl sample was performed (gray solid and dotted lines, respectively). The DSC curve of the first heating is similar to the curve obtained by Giron et al [14]. The Netzsch Thermal Analysis software was used to determine the temperatures of the peaks.…”

Section: Thermal Investigations Of Racemic Bupihclmentioning

confidence: 82%

“…Commercial 'as is' bupivacaine hydrochloride was determined by Giron et al [14] to be a monohydrate which transforms into an anhydrous form upon heating. They also showed the potential existence of solvates with ethanol, isopropanol, and ethyl acetate.…”

Section: Introductionmentioning

confidence: 99%

“…Temperature-resolved X-ray experiments performed by Giron et al demonstrated the existence of two anhydrous forms. The forms were detected by heating and cooling processes fluctuating between 100 and 170°C [14]. Furthermore, four new forms of BupiHCl were discovered by utilization of the ''Basic Screen'' polymorph screening protocol and were differentiated using instrumental methods such as differential scanning calorimetry (DSC), X-ray powder diffraction (XRPD), and polarized light microscopy (PLM).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Thermal and X-ray analysis of racemic bupivacaine hydrochloride

Sykuła

Łodyga-Chruścińska

Pałecz

et al. 2011

J Therm Anal Calorim

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An amide-type local anesthetic drug, bupivacaine hydrochloride (BupiHCl), in the form of racemate is listed in the European and American pharmacopoeias and continues to be used in medicine. Thermal and X-ray analysis of commercial BupiHCl monohydrate was performed by differential scanning calorimetry with thermogravimetry, hot stage microscopy, and X-ray diffraction. Endothermic dehydration occurs at the temperature range of 73-130°C for DSC-TG 111 (Setaram) and at 83-150°C for DSC 404 (Netzsch). Both curves at 2 and 10°C min -1 clearly reflect phase transformation of anhydrous Form I into II before reaching the melting point. A well-defined exothermic phase transition of BupiHCl was detected at a lower heating rate. Temperature-resolved X-ray diffraction in conjunction with DSC led to determining a similarity between the obtained thermal events. Microscopic investigation also confirmed the above-mentioned transformations.

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Study of the polymorphic behaviour of some local anesthetic drugs

Cited by 34 publications

References 6 publications

Characterization and Comparison of Lidocaine-Tetracaine and Lidocaine-Camphor Eutectic Mixtures Based on Their Crystallization and Hydrogen-Bonding Abilities

Characterization and Comparison of Lidocaine-Tetracaine and Lidocaine-Camphor Eutectic Mixtures Based on Their Crystallization and Hydrogen-Bonding Abilities

Water Vapor Adsorption Behavior of Sodium Deoxycholate Anhydrous Forms

Thermal and X-ray analysis of racemic bupivacaine hydrochloride

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