Spectral characterization of fluconazole

Cyr, Terry D.; Dawson, Brian; Neville, George A.; Shurvell, H. F.

doi:10.1016/0731-7085(95)01598-1

Cited by 37 publications

(33 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reason for having difference between measured and estimated solubilities of anhydrate form II, may be due to the transformation of anhydrate form II to stable fluconazole monohydrate before the solubility of metastable anhydrate form II could reach its equilibrium value. 28) In conclusion, 13 C-SSNMR spectroscopy is a useful method for presenting of obvious differences in the chemical shift and peak splitting characteristics, reflecting a change in the molecular conformation, between fluconazole polymorphs, anhydrate forms I and II. Furthermore, the results of kinetic solubility and intrinsic dissolution tests indicated that the solubility and initial IDR of anhydrate form II was higher than that of anhydrate form I and fluconazole monohydrate, although the decrease in the solubility and dissolution rate of anhydrate form II is resulted by the transformation from anhydrate form II to most stable fluconazole monohydrate during dissolving procedure.…”

Section: Resultsmentioning

confidence: 99%

“…10) Three anhydrate polymorphic forms, one monohydrate and several solvates of fluconazole, have been prepared and characterized. [11][12][13][14][15][16][17][18][19][20] However, there has been no published research involving the characterization of fluconazole polymorphs using SSNMR spectroscopy. Consequently, we investigate the characterization of two fluconazole polymorphs, anhydrate forms I and II prepared by the supercritical antisolvent (SAS) process using SSNMR spectroscopy to obtain the structural differences in molecular level between fluconazole polymorphs.…”

mentioning

confidence: 99%

“…The solution state 13 C-NMR spectra were also obtained from deuterodimethyl sulfoxide (DMSO-d 6 ) solutions of samples using a JNM-AL400 (JEOL Ltd., Japan) at 400 MHz. FT-IR spectroscopy was performed on a FT-IR spectrometer (Bruker, FT-IR Tensor 27, Germany) using the attenuated total reflectance (ATR) method.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Solid-State Carbon NMR Characterization and Investigation of Intrinsic Dissolution Behavior of Fluconazole Polymorphs, Anhydrate Forms I and II

Park

Kim

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

NotePolymorphism is defined as the occurrence of different crystalline forms of the same pure compound in which the molecules have different arrangement and/or conformation. 1)Many drugs are able to be crystallized in several polymorphic forms, each having a different energy and thereby differing in physicochemical and mechanical properties such as melting point, solubility, stability, heat of fusion, density, refractive index, compression behavior and hygroscopicity. 2)Supercritical fluid (SCF) based technologies are currently valid tools among various crystallization techniques to control the polymorphic form of pharmaceuticals.3) The differences of properties such as solubility may have implications for absorption of the active drug from its dosage form. These concerns have led to an increased regulatory interest in the solid-state properties. 4,5) Solid state NMR (SSNMR) spectroscopy is also an essential technique for the solid state characterization of pharmaceuticals. The SSNMR spectroscopy not only differentiates between polymorphic forms of a pharmaceutical, but also intimately probes the structural aspects of polymorphic form. 6) Furthermore, solid state proton relaxation time (T 1 ) studies can also provide useful information on molecular motion in the solid state. 7)Intrinsic dissolution test is a one of the attempt to measure the solubility of a metastable polymorph which can undergo a phase transformation to the more stable phase during dissolving procedure. In fact, equilibrium solubility may not be very relevant for study of polymorphs if polymorphs are physically unstable in the aqueous environment. Instead, intrinsic dissolution rate (IDR) and kinetic solubility may be more relevant parameters to consider while studying the oral absorption of polymorphs. 2,8,9) Fluconazole is designated chemically as 2,4-difluoroa,a 1 -bis(1H-1,2,4-triazol-L-ylmethyl) benzyl alcohol ( Fig. 1) and is the first of a new subclass of synthetic triazole antifungal agent.10) Three anhydrate polymorphic forms, one monohydrate and several solvates of fluconazole, have been prepared and characterized.11-20) However, there has been no published research involving the characterization of fluconazole polymorphs using SSNMR spectroscopy. Consequently, we investigate the characterization of two fluconazole polymorphs, anhydrate forms I and II prepared by the supercritical antisolvent (SAS) process using SSNMR spectroscopy to obtain the structural differences in molecular level between fluconazole polymorphs. General solid state characterization such as differential scanning calorimetry (DSC), Powder X-ray diffraction (PXRD), fourier transform infrared (FT-IR) and Raman spectroscopy were also performed. Furthermore, kinetic solubility and intrinsic dissolution tests in aqueous solution were performed to investigate the solubility profiles and dissolution properties of fluconazole polymorphs. ExperimentalMaterials Micronized fluconazole (99.0% purity) was kindly provided Hwail Pharm. Co., Ltd. (Korea). The CO 2 used was 99.9% p...

show abstract

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Solid-State Carbon NMR Characterization and Investigation of Intrinsic Dissolution Behavior of Fluconazole Polymorphs, Anhydrate Forms I and II

Park

Kim

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

View full text Add to dashboard Cite

show abstract

“…6). For fluconazole, the vibrations of the various functional groups present in the molecule could be attributed to a broad band due to hydrogen bonded O-H stretching vibrations in the range of 3,600-2,500 cm -1 ; 1,619 and 1,514 cm -1 bands due to C=C stretch aromatic ring; 1,502 and 1,420 cm -1 bands due to triazole ring stretch; 1,273 cm -1 for C-F stretch; 1,138 cm -1 for triazole ring breathing; 1,020 cm -1 for C-H aromatic ring; 967 and 846 cm -1 for C-H triazole ring [54,55].…”

Section: Fourier Transform Infrared Spectroscopy (Ftir)mentioning

confidence: 99%

Fluconazole–excipient compatibility studies as the first step in the development of a formulation candidate for biowaiver

Teleginski

Maciel

Mendes

et al. 2014

J Therm Anal Calorim

View full text Add to dashboard Cite

The biowaiver of bioequivalence studies on class I drugs of the biopharmaceutics classification system (BCS) is aimed mainly at reducing the costs and the exposure of health volunteers to a new pharmaceutical formulation. Fluconazole is an important antifungal agent but in the literature it is not clear whether it belongs to BCS class I or III. Compatibility studies are considered to be the first step in product development and on considering a biowaiver candidate these gain even greater importance since the final product will not be submitted to in vivo tests. The aim of this study was to qualitatively determine the composition of a commercially available fluconazole formulation in the form of capsules with regard to the presence of critical excipients and to carry out compatibility studies by differential scanning calorimetry (DSC). One formulation did not contain sodium lauryl sulfate and contained mannitol, in contrast to the reference formulation, which could hinder the acceptance of the biowaiver. The interaction of fluconazole with microcrystalline cellulose and calcium hydrogen phosphate dihydrate was observed; however, no indication of incompatibility was found in the DSC analysis of the commercial pharmaceutical formulations. These interactions were also studied by Fourier transform infrared spectroscopy, where small changes in the bands were observed, and by X-ray Powder diffraction and scanning electron microscopy that did not evidence any modification in the solid state characteristics.

show abstract

“…[44] The highest peak was observed at m/z = 361 corresponding to ofloxacin. Peaks at m/z = 245 and 217 corresponded to the fragments of ofloxacin.…”

Section: Gc-mass Spectramentioning

confidence: 98%

Antibacterial, SOD mimic and nuclease activities of copper(II) complexes containing ofloxacin and neutral bidentate ligands

Patel

Parmar

Gandhi

2010

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

Spectral characterization of fluconazole

Cited by 37 publications

References 10 publications

Solid-State Carbon NMR Characterization and Investigation of Intrinsic Dissolution Behavior of Fluconazole Polymorphs, Anhydrate Forms I and II

Solid-State Carbon NMR Characterization and Investigation of Intrinsic Dissolution Behavior of Fluconazole Polymorphs, Anhydrate Forms I and II

Fluconazole–excipient compatibility studies as the first step in the development of a formulation candidate for biowaiver

Antibacterial, SOD mimic and nuclease activities of copper(II) complexes containing ofloxacin and neutral bidentate ligands

Contact Info

Product

Resources

About