Cocrystals of itraconazole with amino acids: Screening, synthesis, solid state characterization, in vitro drug release and antifungal activity

Shete, Amol; Murthy, Srinivasa; Korpale, Snehal; Yadav, Adhikrao Vyankatrao; Sajane, Sachin; Sakhare, Sfurti; Doijad, Rajendra

doi:10.1016/j.jddst.2015.05.006

Cited by 40 publications

(21 citation statements)

References 24 publications

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“…homosynthons or heterosynthons [72] . Cocrystals of itraconazole was prepared with succinic acid and serine by using this method and the results showed the highest in vitro solubility and dissolution rate as compared to all other formulations [70] .…”

Section: Cocktail Cocrystal Methodmentioning

confidence: 99%

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Pharmaceutical Cocrystals: An Overview

Kumar¹,

Nanda²

2017

pharmaceutical-sciences

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Section: Cocktail Cocrystal Methodmentioning

confidence: 99%

“…It was demonstrated that the two components should be miscible if total HSPs difference was <7MP a 0.5 , otherwise immiscible [68] . Another method estimates the miscibility of two components if the difference is ≤5 MP 0.5 between two substances which are supposed to be cocrystal formation [69,70] .…”

Section: Hansen Solubility Parametermentioning

confidence: 99%

Pharmaceutical Cocrystals: An Overview

Kumar¹,

Nanda²

2017

pharmaceutical-sciences

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“…when the novel drugs are unavailable or too expensive . A huge disadvantage of itraconazole lies however in its bioavailability—it is poorly soluble in water (5 μg/mL) and usually has to be administered as a dispersion (most commonly, cyclodextrins are used for this purpose) .…”

Section: Introductionmentioning

confidence: 99%

Analytical and semipreparative chiral separation ofcis-itraconazole on cellulose stationary phases by high-performance liquid chromatography

2016

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cis-Itraconazole is a chiral antifungal drug administered as a racemate. The knowledge of properties of individual cis-itraconazole stereoisomers is vital information for medicine and biosciences as different stereoisomers of cis-itraconazole may possess different affinity to certain biological pathways in the human body. For this purpose, either chiral synthesis of enantiomers or chiral separation of racemate can be used. This paper presents a two-step high-performance liquid chromatography approach for the semipreparative isolation of four stereoisomers (two enantiomeric pairs) of itraconazole using polysaccharide stationary phases and volatile organic mobile phases without additives in isocratic mode. The approach used involves the separation of the racemate into three fractions (i.e. two pure stereoisomers and one mixed fraction containing the remaining two stereoisomers) in the first run and consequent separation of the collected mixed fraction in the second one. For this purpose, combination of cellulose tris-(4-methylbenzoate) and cellulose tris-(3,5-dimehylphenylcarbamate) columns with complementary selectivity for cis-itraconazole provided full separation of all four stereoisomers (with purity of each isomer > 97%). The stereoisomers were collected, their optical rotation determined and their identity confirmed based on the results of a previously published study. Pure separated stereoisomers are subjected to further biological studies.

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“…101 Recent studies with various pharmaceutical compounds with diverse chemical and pharmacological nature which includes myricetin (anticancer flavonol), itraconazole (antifungal), adefovir (antiviral), aceclofenac (nonsteroidal anti-inflammatory) and mirtazapine (antidepressant) reemphasize the solubility advantage of cocrystals exhibiting potential to improve bioavailability. [102][103][104][105][106] Effect of pH and pKa on eutectic point or transition concentrations cocrystal was shown by Bethune SJ, et al 107 It was demonstrated how cocrystal solubility of nonionizable API can be influenced by pH, pKa, and coformer concentration through mathematical prediction tools. This study was carried out for cocrystals carbamazepine with salicylic acid and p-aminobenzoic acid coformers, which can be exploited to study the behavior of other API's with acidic and basic nature.…”

mentioning

confidence: 99%