Drug-drug cocrystals of antituberculous 4-aminosalicylic acid: Screening, crystal structures, thermochemical and solubility studies

Drozd, Ksenia V.; Manin, Alex N.; Churakov, Andrei V.; Perlovich, German L.

doi:10.1016/j.ejps.2016.12.016

Cited by 48 publications

(25 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[33] Nevertheless, co-crystal forms may also decrease pure drug solubility,a s PASA-theophylline( TPH) lowersP ASA solubility by approximately twofold. [33] This has been also evidenced by,f or example, the work of Grossjohann etal. with the benzamide (BA)dibenzyls ulfoxide (DBSO) 1:1c o-crystal, embedding the poorly water soluble DBSO with the more soluble BA.…”

Section: Solid Forms and Their Implications On Physical Chemical Phmentioning

confidence: 99%

State of the Art of Pharmaceutical Solid Forms: from Crystal Property Issues to Nanocrystals Formulation

et al. 2018

View full text Add to dashboard Cite

The solid‐form screening of active principal ingredients is a challenge for pharmaceutical drug development, as more than 80 % of marketed drugs are formulated in the solid form. A broad and comprehensive study of the various solid forms of drugs is needed to enhance their translation into the clinic. Therefore, the most suitable solid form must be taken into consideration regarding ex vivo and in vivo stability, targeting, solubility, dissolution rate, and bioavailability. In this review, techniques of solid‐form screening are covered, including differences in solid forms such as polymorphs, solvates, salts, co‐crystals, and amorphous particles. Moreover, solid drug size reduction is also discussed, with insight into the emergence of drug nanocrystal formulations. An overview of the smallest nanocrystals reported in the literature and on the market is also provided, along with their applications and routes of administration.

show abstract

Section: Solid Forms and Their Implications On Physical Chemical Phmentioning

confidence: 99%

State of the Art of Pharmaceutical Solid Forms: from Crystal Property Issues to Nanocrystals Formulation

et al. 2018

View full text Add to dashboard Cite

show abstract

“…They found that the co-crystal formed between DIF and PZA was compatible with the respective pharmacological effects of two parent drugs, and the aqueous solubility of DIF was enhanced efficiently by the co-crystallization process. Drozd et al 15 utilized two co-crystals of anti-TB drugs between INH and 4-aminosalicylic acid to verify whether a potential synergistic effect existed over the API combinations, which consequently led to further therapeutic advantages. In addition, Cherukuvada et al 11 failed in their attempt to make a binary co-crystal using PZA and INH through the solution crystallization and grinding eutectic composition experiments, which was due to the shape incompatibility of these two parent drugs.…”

Section: Introductionmentioning

confidence: 99%

Vibrational Spectroscopic Investigation into Novel Ternary Eutectic Formed between Pyrazinamide, Fumaric Acid, and Isoniazid

et al. 2020

View full text Add to dashboard Cite

To improve the efficacy of anti-tuberculosis (anti-TB) therapy, drug–drug co-crystallization stands for an alternative approach to settle the tuberculosis problem. Directly co-crystallizing two typical parent anti-TB drugs (pyrazinamide, PZA and isoniazid, INH) into a single binary co-crystal could not be obtained successfully. Multicomponent eutectic are highly effective and useful for enhancing the dissolution rate, bioavailability, and physical stability of the poorly water-soluble active pharmaceutical ingredient (API) drugs, when the attempts of forming a binary co-crystal have failed. Therefore, the ternary eutectic composition conception was proposed in this study, in which fumaric acid (FA) was chosen as the molecule to connect two first-line anti-tubercular drugs. First of all, three starting materials (including PZA, INH, and FA) were grinded at a 1:1:1 molar ratio, the eutectic composition was investigated through vibrational spectroscopic techniques, including terahertz time-domain spectroscopy (THz-TDS) and Raman spectroscopy. Additionally, the density functional theory (DFT) was utilized to simulate the optimized structures and vibrational modes of two possible theoretical eutectic composition forms. The THz absorption spectrum of the theoretical form I shows much more consistency with the experimental results than that of form II. Raman spectra also help to characterize the differences in vibrational modes between the eutectic composition and the starting parent compounds. The results provide us with both structural information and intermolecular hydrogen bonding interactions within specific multicomponent eutectic composition formulations based on Raman and terahertz vibrational spectroscopic techniques in combination with theoretical calculations.

show abstract

“…As proof‐of‐concept we have developed four new co‐crystals based on isonicotinamide (INCT, Figure 1). INCT has been used extensively as a pharmaceutical co‐former to improve the solubility of an API without compromising its efficacy or stability [11–22] . INCT is able to act as a hydrogen bond acceptor through the pyridine group, and the amide moiety is capable of engaging in a wide range of different hydrogen‐bonding motifs.…”

Section: Introductionmentioning

confidence: 99%

Mechanistic In Situ and Ex Situ Studies of Phase Transformations in Molecular Co‐Crystals

Clout

Buanz

Pang

et al. 2020

Chemistry A European J

View full text Add to dashboard Cite

Co-crystallisation is widely explored as ar oute to improve the physical properties of pharmaceuticala ctive ingredients, but little is known about the fundamental mechanisms of the process. Herein, we apply ah yphenated differential scanning calorimetry-X-ray diffraction technique to mimic the commercialh ot melt extrusion process, and explore the heat-induceds ynthesis of as eries of new co-crystals containingi sonicotinamide. These comprise a1 :1 cocrystal with 4-hydroxybenzoica cid, 2:1a nd 1:2s ystemsw ith 4-hydroxyphenylacetic acid anda1:1c rystal with 3,4-dihydroxyphenylactic acid. Thef ormationo fc o-crystalsd uring heating is complex mechanistically.I na ddition to co-crystallisation, conversions betweenp olymorphs of the co-former starting materials and co-crystal products are also observed. As ubsequents tudy exploring the use of inkjet printing and millingt og enerate co-crystals revealed that the synthetic approachh as am ajor effecto nt he co-crystal speciesa nd polymorphs produced.

show abstract

Drug-drug cocrystals of antituberculous 4-aminosalicylic acid: Screening, crystal structures, thermochemical and solubility studies

Cited by 48 publications

References 28 publications

State of the Art of Pharmaceutical Solid Forms: from Crystal Property Issues to Nanocrystals Formulation

State of the Art of Pharmaceutical Solid Forms: from Crystal Property Issues to Nanocrystals Formulation

Vibrational Spectroscopic Investigation into Novel Ternary Eutectic Formed between Pyrazinamide, Fumaric Acid, and Isoniazid

Mechanistic In Situ and Ex Situ Studies of Phase Transformations in Molecular Co‐Crystals

Contact Info

Product

Resources

About