644-62-2Relevant articles and documents
Synthesis, crystal structures and spectroscopy of meclofenamic acid and its metal complexes with manganese(II), copper(II), zinc(II) and cadmium(II). Antiproliferative and superoxide dismutase activity
Kovala-Demertzi, Dimitra,Staninska, Malgorzata,Garcia-Santos, Isabel,Castineiras, Alfonso,Demertzis, Mavroudis A.
, p. 1187 - 1195 (2011)
Some new complexes of meclofenamic acid (N-(2,6-dichloro-m-tolyl) anthranilic acid), Hmeclo (1), with potentially interesting biological activities are described. Complexes [Mn(meclo)2] (2), [Cu(meclo) 2(H2O)2] (3), [Zn(meclo)2(H 2O)2] (4) and [Cd(meclo)2(H2O) 2] (5) were prepared and structurally characterized by means of vibrational, electronic and 1H and 13C NMR spectroscopies. The crystal structure of complexes [Cu4(meclo)6(OH) 2(DMSO)2]2DMSO (3a) and [Cd(meclo)2(DMSO) 3] (5a) have been determined by X-ray crystallography. Complex (3a) is a centrosymmetric tetramer built up around the planar cyclic Cu 2(OH)2 unit. Complex 5a is mononuclear seven-coordinated complex with the meclofenamato ligand behaving as a bidentate deprotonated chelating ligand. Intra and intermolecular hydrogen bonds stabilize these two structures, while the crystal packing is determined by π-π and C-H - π interactions. Meclofenamic acid and its metal complexes have been evaluated for antiproliferative activity in vitro against the cells of three human cancer cell lines, MCF-7 (breast cancer cell line), T24 (bladder cancer cell line), and A-549 (non-small cell lung carcinoma), and a mouse fibroblast L-929 cell line. Complex 5 exhibits the highest selectivity against MCF-7 and 4 shows the highest selectivity against T-24. Complexes 2-5 were found to be more potent cytotoxic agents against T-24 and complex 5 against MCF-7 cancer cell lines than the prevalent benchmark metallodrug, cis-platin. The superoxide dismutase activity was measured by the Fridovich test which showed that complex [Cu(meclo) 2(H2O)2] is a good superoxide scavenger.
High solubility piperazine salts of the nonsteroidal anti-inflammatory drug (NSAID) meclofenamic acid
Sanphui, Palash,Bolla, Geetha,Nangia, Ashwini
body text, p. 2023 - 2036 (2012/06/30)
Meclofenamic acid (MFA) is the most potent anti-inflammatory drug among the fenamic acids. We report (1) two cocrystals of MFA with isonicotinamide (INA) and 4,4′-bipyridine (BPY); (2) polymorphs of MFA and piperazine (PPZ) 1:1 salt (orthorhombic P212121 O and monoclinic P21/c M), MFA-PPZ-H2O 1:1:1 salt hydrate, MFA-PPZ 2:1 salt; and (3) MFA and 2-aminopyridine (2-APY) 1:1 salt, MFA and 4-aminopyridine (4-APY) 1:1:1 salt hydrate. Sublimation of MFA gave single crystals for X-ray diffraction which provided good quality data for refinement and all atomic coordinates. The cocrystal and salt structures are assembled via neutral O-H???O, O-H???N, N-H???O, N-H???N, and ionic O-H???O-, N +-H???O- hydrogen bonds. The disorder of the methyl group in the MFA crystal structure is absent in the cocrystal and salt structures, which contain different conformers (A or B) of methyl group orientation. The solubility of MFA-INA (1:1) and MFA-BPY (1:0.5) cocrystals is 2.9 and 7.6 times higher than that of MFA at 37 °C in 50% EtOH-water. Interestingly, MFA-PPZ-M 1:1 salt and its 1:1:1 hydrate are 2724- and 1334-fold more soluble than MFA. Both of these salts transformed in 50% EtOH-water slurry at 37 °C to MFA-PPZ 2:1 salt after 24 h, which in turn transformed to MFA after another 24 h of slurry stirring. Remarkably, the dissolution rate of MFA-PPZ-M (1:1) salt in water is just slightly lower than that of the marketed sodium meclofenamate.
Methods for use of GABAa receptor GABAergic compounds
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, (2008/06/13)
A method is disclosed for potentiating mammalian GABA A receptor responses to GABA. The receptor responses are potentiated according to the invention by contacting GABA A receptors with GABA and an effective amount of non-steroidal anti-inflammatory agents, in particular, fenamates and structurally related compounds.
