Synthesis and structural characterization of cocrystals of isoniazid and cinnamic acid derivatives

Mashhadi, Syed Muddassir Ali; Yufit, D. S.; Liu, Huiyu; Hodgkinson, Paul; Yunus, Uzma

doi:10.1016/j.molstruc.2020.128621

Cited by 15 publications

(8 citation statements)

References 49 publications

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“…Next, combining trimethoprim with 2,4-diaminopyrimidines pyrimethamine as a co-former built a crystal system with higher stability [80]. Afterward, sulfamethoxazole and succinimide multi-component solids showed higher stability than the base form [80,82]. In addition, cephalosporin with thymol produced a cocrystal that affected antibiotic activity [81].…”

Section: Complexation Reaction Increased Photocatalysismentioning

confidence: 99%

“…The multi-component systems comprising isoniazid-acid substituents and natural resources were the following: isoniazid combined with cinnamic acid, fumaric acid [74,82,85,86], mandelic acid [82,91], glutaric acid [84], pimelic acid [84], malonic acid [84], hydroxybenzoic acid [86], adipic acid [84,86], gallic acid [86], gentisic acid [82,86], succinic acid and nicotinamide [88], glycolic acid [91], benzoic acid [90], ferulic acid [98], and oleanolic acid [93], etc., which some of them enhancing stability and solubility, and others decreasing those parameters. It has been hypothesized that the carboxylic acid substitution changes isoniazid's stability and solubility.…”

Section: Complexation Reaction Increased Photocatalysismentioning

confidence: 99%

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The Benefits and Challenges of Antibiotics–Non-Steroidal Anti-Inflammatory Drugs Non-Covalent Reaction

2023

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Recently, non-covalent reactions have emerged as approaches to improve the physicochemical properties of active pharmaceutical ingredients (API), including antibiotics and non-steroidal anti-inflammatory drugs (NSAIDs). This review aimed to present and discuss the non-covalent reaction products of antibiotics, including salt and neutral multi-component solid forms, by framing their substituents and molar ratios, manufacturing techniques, characterization methods, benefits, potency changes, and toxicity, and is completed with an analysis of the development of computational models used in this field. Based on the data, NSAIDs are the most-developed drugs in multi-component system preparations, followed by antibiotics, i.e., antituberculosis and fluoroquinolones. They have reacted with inorganic elements, excipients, nutraceuticals, natural products, and other drugs. However, in terms of treatments for common infections, fluoroquinolones are more frequently used. Generally, NSAIDs are acquired on an over-the-counter basis, causing inappropriate medication. In addition, the pKa differences between the two groups of medicine offer the potential for them to react non-covalently. Hence, this review highlights fluoroquinolone–NSAID multi-component solid systems, which offer some benefits. These systems can increase patient compliance and promote the appropriate monitoring of drug usage; the dual drug multi-component solids have been proven to improve the physicochemical properties of one or both components, especially in terms of solubility and stability. In addition, some reports show an enhancement of the antibiotic activity of the products. However, it is important to consider the possibility of activity changes, interaction, and toxicity when using drug combinations. Hence, these aspects also are discussed in this review. Finally, we present computational modeling, which has been utilized broadly to support multi-component system designs, including coformer screening, preparation methods, and structural modeling, as well as to predict physicochemical properties, potency, and toxicity. This integrated review is expected to be useful for further antibiotic–NSAID multi-component system development.

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Section: Complexation Reaction Increased Photocatalysismentioning

confidence: 99%

Section: Complexation Reaction Increased Photocatalysismentioning

confidence: 99%

The Benefits and Challenges of Antibiotics–Non-Steroidal Anti-Inflammatory Drugs Non-Covalent Reaction

2023

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“…INH potential as a supramolecular building block [17] is primarily due to its pyridine N atom and the hydrazide group being complementary with carboxylic acid and hydroxyl groups, which allows to design particularly stable synthons. [18] Bernstein and coworkers [19][20][21] [23,24] , Cocrystals of INH with antioxidants may provide relief in oxidative stress in patients of Tuberculosis during treatment and increases tabletting shelf life [23,25,26] as well. Gentisic (dihydroxybenzoic) acid is an active metabolite of salicylic acid degradation and a by-product of tyrosine and benzoate metabolism.…”

Section: Tuberculosis (Tb) Is Considered As a Global Emergency By World Health Organization (Who)mentioning

confidence: 99%

Isoniazid-Gentisic acid cocrystallization: Solubility, Stability, Dissolution rate, Antioxidant and Flowability Properties Studies

Mashhadi

Batsanov

Sajjad

et al. 2021

Journal of Molecular Structure

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Isoniazid (INH) is a key antitubercular agent, which exhibits poor chemical stability in the solid state associated with the hydrazide group. Cocrystallization with Gentisic Acid having antioxidant activity, may produce solid forms with improved pharmaceutical properties. The complementary nature of the functional groups of isoniazid and the chosen coformer resulted in success for cocrystal formation. Cocrystal (INH-Gentisic acid) was characterized by solid-state NMR, DSC, PXRD and single crystal-XRD. The synthesized cocrystals were tested for the inhibition of synthetic-free radicals, DPPH. INH-Gentisic acid demonstrated high free radical scavenging activity against DPPH (78.36% for 125µg/ml concentration) which were better than that of ascorbic acid (37.16%) used as standard. Moreover solubility, stability and flowability properties of the synthesized cocrystals are optimized.

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“…The dihedral angle between A/B, A/C, and B/C is 10) 157 Symmetry codes: 1 2-x, 1-y, 1-z; 2 2-x, 1-y, -z; 3 2-x, -y, -z; 4 1-x, -y, -z; 5 1-x, 1-y, 1-z; 6 1-x, -y, 1-z; 7 +x, +y, 1+z, 8 -x+1, -y+1, -z+1. Cg1 is the centroid of the phenyl ring (C20A-C25A).…”

Section: Single Crystal Structurementioning

confidence: 99%

“…Multicomponent crystals [1], such as salts, cocrystals [2][3][4][5], and solvates / hydrates, play a key role in the design of novel solid forms, especially in the pharmaceutical arena. Solid forms display exclusive physicochemical properties influencing key features of the formulated API like bioavailability, stability, flowability and manufacturability [6].…”

Section: Introductionmentioning

confidence: 99%

Pharmaceutical organic salt: Disordered crystal structure of levofloxacin with γ-resorcylic acid

et al. 2021

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This study reports an organic salt prepared from an antibacterial drug, levofloxacin and antioxidant γ-resorcylic acid. A simple preparation method leads to a crystal with disordered structure. The idea is to prepare an organic salt comprising of pharmaceutically acceptable acidic and basic components. The salt is characterised by IR, solid state NMR, and single crystal XRD. Crystal data for C25H26N3O8F: triclinic, space group P-1 (no. 2), a = 7.0037(8) Å, b = 12.764(3) Å, c = 13.909(3) Å, α = 104.821(4)°, β = 92.039(4)°, γ = 95.334(4)°, V = 1194.6(4) Å3, Z = 2, T = 296(2) K, μ(MoKα) = 0.113 mm-1, Dcalc = 1.433 g/cm3, 16879 reflections measured (5.048° ≤ 2Θ ≤ 54.186°), 5139 unique (Rint = 0.0663, Rsigma = 0.0975) which were used in all calculations. The final R1 was 0.1121 (I>2σ(I)) and wR2 was 0.2505 (all data). SC-XRD analysis shows that the crystal packing is stabilized by strong H-bonding of type N-H···O and comparatively weak interactions of type C-H···O, C-H···π and off-set π···π stacking.

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Synthesis and structural characterization of cocrystals of isoniazid and cinnamic acid derivatives

Cited by 15 publications

References 49 publications

The Benefits and Challenges of Antibiotics–Non-Steroidal Anti-Inflammatory Drugs Non-Covalent Reaction

The Benefits and Challenges of Antibiotics–Non-Steroidal Anti-Inflammatory Drugs Non-Covalent Reaction

Isoniazid-Gentisic acid cocrystallization: Solubility, Stability, Dissolution rate, Antioxidant and Flowability Properties Studies

Pharmaceutical organic salt: Disordered crystal structure of levofloxacin with γ-resorcylic acid

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