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Open AccessArticle

A Comprehensive Study of a New 1.75 Hydrate of Ciprofloxacin Salicylate: SCXRD Structure Determination, Solid Characterization, Water Stability, Solubility, and Dissolution Study

1
Department of Pharmacochemistry, School of Pharmacy, Bandung Institute of Technology, Bandung 40132, Indonesia
2
Department of Chemistry, Tokyo Institute of Technology, Tokyo 152-8551, Japan
*
Authors to whom correspondence should be addressed.
Crystals 2020, 10(5), 349; https://doi.org/10.3390/cryst10050349
Received: 7 March 2020 / Revised: 16 April 2020 / Accepted: 17 April 2020 / Published: 28 April 2020
One problem that often arises during the formulation of a dosage form is the solubility and dissolution of the active ingredients. This problem arises in ciprofloxacin, which is a BCS class IV fluoroquinolone antibiotic. A pseudopolymorph is a kind of polymorph in which the number of hydrates is different. In this study, a new pseudopolymorph comprised of ciprofloxacin and salicylic acid was found, namely the salt ciprofloxacin salicylate 1.75 hydrate form. This new solid phase was analyzed by Fourier-transform infrared spectroscope (FTIR), Raman spectroscopy, and thermal analysis and proven by Powder X-ray Diffractometry (PXRD) analysis. The crystal structure was successfully determined by Single Crystal X-ray Diffractometry (SCXRD) analysis. It was found that the piperazinyl group of ciprofloxacin is protonated by H+ from the carboxylic group of salicylic acid. In the unit cell, two ciprofloxacin and two salicylic acid molecules were independent with four water molecules, in which one water molecule had 0.5 occupancy due to inversion symmetry. Interestingly, this hydrate crystal dehydrated by grinding for 105 minutes forms an anhydrous crystalline phase, which was analyzed with FTIR, Raman spectroscopy, thermal analysis, and PXRD. The solubility and dissolution tests were carried out using UV-Visible spectrophotometry and a multiple linear regression method. This new hydrate solid phase has a better profile than the original ciprofloxacin crystal, according to the solubility and dissolution tests. View Full-Text
Keywords: ciprofloxacin; salycilic acid; pseudopolymorph; solubility enhancing; dissolution enhancing; dehydration; milling; raman spectroscopy; multilinear regression ciprofloxacin; salycilic acid; pseudopolymorph; solubility enhancing; dissolution enhancing; dehydration; milling; raman spectroscopy; multilinear regression
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MDPI and ACS Style

Nugrahani, I.; Tjengal, B.; Gusdinar, T.; Horikawa, A.; Uekusa, H. A Comprehensive Study of a New 1.75 Hydrate of Ciprofloxacin Salicylate: SCXRD Structure Determination, Solid Characterization, Water Stability, Solubility, and Dissolution Study. Crystals 2020, 10, 349.

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