Solid Forms of Ciprofloxacin Salicylate: Polymorphism, Formation Pathways, and Thermodynamic Stability

  title={Solid Forms of Ciprofloxacin Salicylate: Polymorphism, Formation Pathways, and Thermodynamic Stability},
  author={Artem O. Surov and Nikita A. Vasilev and Andrei V. Churakov and Julia Stroh and Franziska Emmerling and German L. Perlovich},
  journal={Crystal Growth \& Design},
The crystallization of ciprofloxacin—an antibacterial fluoroquinolone compound—with salicylic acid resulted in the isolation of five distinct solid forms of the drug, namely, an anhydrous salt, two... 

Crystalline Multicomponent Solids: An Alternative for Addressing the Hygroscopicity Issue in Pharmaceutical Materials

The ambient humidity varies with seasons and geographical altitude across the regions. A change in relative humidity during processing, storage, and transportation can cause instability to the acti...

Fluoroquinolone-Based Organic Salts and Ionic Liquids as Highly Bioavailable Broad-Spectrum Antimicrobials

In vitro bioavailability studies showed that all prepared FQ-OSILs presented higher solubility in water than the original drugs, and all compounds were found to be isomorphic and with tailorable antimicrobial activity according to the cation–anion combination against Staphylococcus aureus, Bacillus subtilis and Klebsiella pneumoniae strains.

Ciprofloxacin salts with benzoic acid derivatives: structural aspects, solid-state properties and solubility performance

In this work, three new pharmaceutical hydrated salts of ciprofloxacin with selected derivatives of benzoic acid, namely 4-hydroxybenzoic acid, 4-aminobenzoic acid and gallic acid, were obtained and

Antimicrobial Activities of Highly Bioavailable Organic Salts and Ionic Liquids from Fluoroquinolones

Depending on the cation–drug combination, broad-spectrum or strain-specific antibiotic salts were achieved, potentially leading to the future development of highly bioavailable and safe antimicrobial ionic formulations.

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

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

Trimolecular Co-crystals of Ciprofloxacin, p-Coumaric Acid, and Benzoic Acid or Salicylic Acid

Molecular salts formation is a simple and widely used approach to alter the physicochemical properties of active pharmaceutical ingredients, such as ciprofloxacin (CP), without modifying their

Selective Synthesis of a Salt and a Cocrystal of the Ethionamide–Salicylic Acid System

Herein is presented a rare example of salt/cocrystal polymorphism involving the adduct between ethionamide (ETH) and salicylic acid (SAL). Both the salt and cocrystal forms have the same

Formation of Ciprofloxacin–Isonicotinic Acid Cocrystal Using Mechanochemical Synthesis Routes—An Investigation into Critical Process Parameters

The mechanochemical synthesis of cocrystals has been introduced as a promising approach of formulating poorly water-soluble active pharmaceutical ingredients (APIs). In this study, hot-melt extrusion

A Review on Significance of Identifying an Appropriate Solid Form Duringdrug Discovery and Product Development

Solid form screening studies guide an important decision-making of lead solid form which is likely to play a vital role during the pharmaceutical product development lifecycle.



New Solid Forms of the Antiviral Drug Arbidol: Crystal Structures, Thermodynamic Stability, and Solubility.

Analysis of the conformational preferences of the Arbidol molecule in the crystal structures showed that it adopts two types of conformations, namely "open" and "closed", both of which correspond to local conformational energy minima of the isolated molecule.

Ciprofloxacin Hippurate Salt: Crystallization Tactics, Structural Aspects, and Biopharmaceutical Performance

Ciprofloxacin is a widely prescribed fluoroquinolone antibacterial for the treatment of several types of bacterial infections; however, it suffers from unfavorable biopharmaceutical characteristics

Two Faces of Ciprofloxacin: Investigation of Proton Transfer in Solid State Transformations

Ciprofloxacin (CIP) can exist in two different forms: the zwitterion and the un-ionized form. While the crystal structure of each has been described independently, the ability of CIP to transform

Characterization of the solubility and solid-state properties of saccharin salts of fluoroquinolones.

These salts would be a good way forward to developing more suitable formulations of these APIs, and showed improved properties with respect to water solubility.

Pharmaceutical salts of ciprofloxacin with dicarboxylic acids.

  • A. SurovA. Manin G. Perlovich
  • Materials Science, Chemistry
    European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences
  • 2015

Polymorphism of Mechanochemically Synthesized Cocrystals: A Case Study

The liquid-assisted grinding cocrystallization of theophylline with benzamide leading to polymorphic compounds was investigated. A solvent screening with 17 different solvents was performed. The

Structural study of benzidamine salicylate in the solid state and in solution.

The vibrational (IR and Raman) and 1H and 13C NMR spectra of the analgesic and anti-inflammatory benzidamine salicylate (Benzasal) have been examined, and the results are described. The crystal

Amorphous Polymeric Drug Salts as Ionic Solid Dispersion Forms of Ciprofloxacin.

Amorphous solid dispersions (ASDs) prepared by ball milling CIP with various polymers found that acidic polymers were necessary for the amorphization of CIP, and may be a viable alternative for formulating C IP with improved solubility, bioavailability, and antimicrobial activity.