Halide salts of antimigraine agents eletriptan and naratriptan

Two polymorphs of safinamide {systematic name: (2S)-2-[4-(3-fluorobenzyloxy)benzylamino]propionamide}, C(17)H(19)FN(2)O(2), a potent selective and reversible monoamine oxidase B (MAO-B) inhibitor, are described. Both forms are orthorhombic and regarded as conformational polymorphs due to the differences in the orientation of the 3-fluorobenzyloxy and propanamide groups. Both structures pack with layers in the ac plane. In polymorph (I), the layers have discrete wide and narrow regions which are complementary when located next to adjacent layers. In polymorph (II), the layer has long flanges protruding from each side, which interdigitate when packed with the adjacent layers. N-H...O hydrogen bonds are present in both structures, whereas N-H...F hydrogen bonding is seen in polymorph (I), while N-H...N hydrogen bonding is seen in polymorph (II).

Section: Commentmentioning

confidence: 91%

Two polymorphs of safinamide, a selective and reversible inhibitor of monoamine oxidase B

Ravikumar

Sridhar

2010

“…Viewing the structural features in the light of the theoretical 5-HT 1B -like receptor model (Moloney et al, 1999), the N1Á Á ÁN2 distances are 5.603 (2), 5.564 (4)/4.682 (4) and 5.566 (3)/4.660 (3) Å for (I), (II) and (III), respectively. The corresponding distance is 5.998 (3) Å in sumatriptan succinate (Ravikumar et al, 2004) (Ravikumar et al, 2008b) and 6.322 (2) Å in naratriptan hydrochloride (Ravikumar et al, 2008b).…”

Section: Figurementioning

confidence: 98%

Frovatriptan salts of aliphatic carboxylic acids

Ravikumar¹,

Sridhar²,

Nanubolu³

et al. 2013

The interaction of the antimigraine pharmaceutical agent frovatriptan with acetic acid and succinic acid yields the salts (±)-6-carbamoyl-N-methyl-2,3,4,9-tetrahydro-1H-carbazol-3-aminium acetate, C14H18N3O(+)·C2H3O2(-), (I), (R)-(+)-6-carbamoyl-N-methyl-2,3,4,9-tetrahydro-1H-carbazol-3-aminium 3-carboxypropanoate monohydrate, C14H18N3O(+)·C4H5O4(-)·H2O, (II), and bis[(R)-(+)-6-carbamoyl-N-methyl-2,3,4,9-tetrahydro-1H-carbazol-3-aminium] succinate trihydrate, 2C14H18N3O(+)·C4H4O4(2-)·3H2O, (III). The methylazaniumyl substitutent is oriented differently in all three structures. Additionally, the amide group in (I) is in a different orientation. All the salts form three-dimensional hydrogen-bonded structures. In (I), the cations form head-to-head hydrogen-bonded amide-amide catemers through N-H···O interactions, while in (II) and (III) the cations form head-to-head amide-amide dimers. The cation catemers in (I) are extended into a three-dimensional network through further interactions with acetate anion acceptors. The presence of succinate anions and water molecules in (II) and (III) primarily governs the three-dimensional network through water-bridged cation-anion associations via O-H···O and N-H···O hydrogen bonds. The structures reported here shed some light on the possible mode of noncovalent interactions in the aggregation and interaction patterns of drug molecule adducts.

“…As part of our structural studies on pharmaceutical compounds (Ravikumar & Sridhar, 2006a,b, 2007aRavikumar et al, 2008;Sridhar & Ravikumar, 2009) and stimulated by the studies on drug-metal interactions, the crystal structures of granisetron, (I), and its cobalt complex, (II), were determined.…”

Section: Commentmentioning

confidence: 99%

Granisetron, an antiemetic drug, and its cobalt complex

Ravikumar

Sridhar

2010

The crystal structures of granisetron [systematic name: 1-methyl-N-(9-methyl-9-azabicyclo[3.3.1]nonan-7-yl)indazole-3-carboxamide], C(18)H(24)N(4)O, (I), an antinauseant and antiemetic agent, and its Co(II) complex, diaqua[1-methyl-N-(9-methyl-9-azoniabicyclo[3.3.1]nonan-7-yl)indazole-3-carboxamide]cobalt(II) tetrachloride dodecahydrate, [Co(C(18)H(25)N(4)O)(2)(H(2)O)(2)]Cl(4).12H(2)O, (II), have been determined by X-ray diffraction. The granisetron molecule is in an extended conformation in both structures. Twisting of the central carboxamide group facilitates the Co(II) coordination in (II). The Co(II) atom is located on an inversion centre. The azabicyclononane ring adopts a chair-boat conformation in both structures. The molecules in (I) are linked into centrosymmetric dimers and form tetracyclic rings through C-H...O hydrogen-bonding interactions. The simultaneous presence of free chloride ions in conjunction with a number of hydration water molecules in (II) provides interesting hydrogen-bond patterns. This study can aid in the investigation of the properties of metal complexes with active pharmaceuticals in which the drug molecules play the role of a ligand.