The influence of a new analgetic-antiphlogistic compound (2-(2-methyl-3′chloro)-anilino-nicotinic acid) on platelet function and fibrinolytic activity in vitro

Widmer, K; Reed, Richard C.; Freireich, Emil J.

doi:10.1016/0049-3848(75)90146-2

Cited by 2 publications

(2 citation statements)

References 9 publications

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“…[2-(2-Methyl-3-chloroanilino)nicotinic acid [clonixin or CLX] (Scheme ) is a nonsteroidal anti-inflammatory drug (NSAID) used to treat inflammation in rheumatism, osteoporosis, collagen diseases, bursitis, and gout . It also exhibited platelet-inhibitory effects, , and recently it was found to be effective for the treatment of acute migraine. , Like most classic NSAIDs, it is a nonselective cyclooxygenase (COX) inhibitor and causes side effects such as ulcer.…”

Section: Introductionmentioning

confidence: 99%

Substituent Electronegativity and Isostructurality in the Polymorphism of Clonixin Analogues

Shen

Yuan

et al. 2018

Crystal Growth & Design

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To gain understanding of how the variation in local weak interactions influences intermolecular interactions and subsequent crystal packing, four analogues of 2-(3-chloro-2-methyl-phenylamino)-nicotinic acid [clonixin] were synthesized by replacing the chlorine with fluorine (1), bromine (2), iodine (3), and hydrogen (4). Compounds 1, 2, and 3 were found to be polymorphic as shown by the discovery of two forms for each (1-I, 1-II; 2-I, 2-II; and 3-I, 3-II, respectively), while compound 4 has only a single identified form. Similar to clonixin, the analogue molecules in their crystals are associated either by the acid−acid dimer homosynthon or the acid−pyridine heterosynthon, depending on the dihedral angle between the two aromatic rings. Moreover, forms 2-I, 2-II, 3-I, and 3-II are isostructural to clonixin forms I and IV, compound 4 is isostructural to compound 1 form I, and 2-II is structurally similar to clonixin form II. The phase behaviors of these polymorphic systems were studied by differential scanning calorimetry, and it was found that 2-II converted into 2-I when heated, 3-II transformed into 3-I upon heating, and 1-II underwent transition into 1-I. Quantum mechanical calculations including conformational energy, hydrogen-bonding strength, lattice energy, and molecular contact were performed to provide further insight into the polymorphism. Given that all halogen derivatives are polymorphic, while the hydrogen analogue (4) is not, our study highlights the importance of intermolecular interactions in determining crystal packing.

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Section: Introductionmentioning

confidence: 99%

Substituent Electronegativity and Isostructurality in the Polymorphism of Clonixin Analogues

Shen

Yuan

et al. 2018

Crystal Growth & Design

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“…Later it was found to show beneficial anti‐inflammatory and analgesic properties with a much smaller ulcerative effect than other non‐steroidal anti‐inflammatory drugs (NSAIDs) It also exhibited platelet‐inhibitory effects, and recently it was found to be effective for the treatment of acute migraine , . Due to its pharmaceutical stability and bioavailability issues, currently microemulsions and clonixin lysinate are used in clinical formulations…”

Section: Introductionmentioning

confidence: 99%

Strong Hydrogen Bond Leads to a Fifth Crystalline Form and Polymorphism of Clonixin

et al. 2017

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Over 30 years since the discovery of four crystal forms (I, II, III and IV) of Clonixin [2-(3-chloro-2-methyl-phenylamino)-nicotinic acid], a fifth form, a dimethylformamide (DMF) solvate, has been obtained by crystal growth in DMF. The new form was characterized by single-crystal X-ray diffraction, FT-IR, and Raman spectroscopy. The crystal structure is stabilized by the strong hydrogen bond between the carboxylic acid OH and the DMF carbonyl whose strength is on par with those of the four solvent-free forms, which are based on either the acid-acid homosynthon or the acid-pyridine heterosynthon, depending on the dihedral angle between the two aromatic rings. This solvate loses DMF to convert into form I, as confirmed by differential scanning calorimetry (DSC) and powder X-ray diffraction (PXRD). Other aspects of this polymorphic/solvatomorphic system were investigated both experimentally and theoretically. Theoretical studies such as lattice energy calculation, hydrogen-bond strength estimation and Hirshfeld analysis were performed, providing further insight into the polymorphism/solvatomorphism of this system. Based on the analysis of the new form and the whole system, more solvates/ cocrystals could be designed and unveiled in due time.[a] Dr.

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The influence of a new analgetic-antiphlogistic compound (2-(2-methyl-3′chloro)-anilino-nicotinic acid) on platelet function and fibrinolytic activity in vitro

Cited by 2 publications

References 9 publications

Substituent Electronegativity and Isostructurality in the Polymorphism of Clonixin Analogues

Substituent Electronegativity and Isostructurality in the Polymorphism of Clonixin Analogues

Strong Hydrogen Bond Leads to a Fifth Crystalline Form and Polymorphism of Clonixin

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