Gliclazide

Parvez, Masood; Arayne, M. Saeed; Zaman, Mashiat; Sultana, Najma

doi:10.1107/s0108270198009883

Cited by 15 publications

(11 citation statements)

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“…In contrastt oc hlorpropamide, tolbutamide and acetohexamide, only one crystalline form has been reported for each of the followingc ompounds:c arbutamide (4-amino-N-(butylcarbamoyl)benzenesulfonamide), [42] gliclazide (N-(hexahydrocyclopenta[c]pyrrol-2(1H)-ylcarbamoyl)-4-methylbenzenesulfonamide) [43] and tolazamide. [44,45] We selected tolazamide for ac ase study,w ith the aim of understanding why this compoundd oes not tend to form polymorphs, and why the only knownp olymorph has ad imer structural motif, whichh as never been observed in the crystal structures of other sulfonylureas.…”

Section: Introductionmentioning

confidence: 99%

Isoenergetic Polymorphism: The Puzzle of Tolazamide as a Case Study

Boldyreva

Arkhipov

Drebushchak

et al. 2015

Chemistry A European J

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In the present case study of tolazamide we illustrate how many seemingly contradictoryr esults that have been obtained from experimental observationsa nd theoretical calculationsc an finally startf ormingaconsistent picture: a" puzzle put together". For many years, tolazamide was considered to have no polymorphs. This made this drug substance unique amongt he large familyo fs ulfonylureas, which was known to be significantly more pronet op olymorphism than many other organic compounds. The present work employs ab road and in-deptha nalysist hat includest he use of optical microscopy,s ingle-crystal and powder X-ray diffraction,I Ra nd Ramans pectroscopies, DSC, semiempiricalP IXEL calculations and DFT of three polymorphs of tolazamide. This case study showsh ow the polymorphs of amolecular crystalc an be overlooked even if discovered serendipitously on one of numerous crystallizations, and how very different molecular packings can be practically isoenergetic but still crystallize quite selectively and transform one into anotherirreversibly upon heating.

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Section: Introductionmentioning

confidence: 99%

Isoenergetic Polymorphism: The Puzzle of Tolazamide as a Case Study

Boldyreva

Arkhipov

Drebushchak

et al. 2015

Chemistry A European J

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“…For general background to gliclazide and the impurities of gliclazide, see: Lebovitz & Feinglos (1983). For the crystal structure of gliclazide, see: Parvez et al (1999); Winters et al (1994).…”

Section: Related Literaturementioning

confidence: 99%

Gliclazide impurity F:N-[(perhydrocyclopenta[c]pyrrol-2-yl)aminocarbonyl]-o-toluenesulfonamide

Wang²,

Pang³

et al. 2012

Acta Cryst E

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The title compound, C15H21N3O3S, is known to be an impurity of gliclazide [systematic name: N-(hexahydro-1H-cyclopenta[c]pyrrol-2-ylcarbamoyl)-4-methylbenzenesulfonamide], a sulfonylurea antidiabetic drug. Gliclazide has a p-tolyl group substituting the sulfonamide functionality, while the title molecule contains an o-tolyl group. Both five-membered fused rings adopt envelope conformations. In the crystal, N—H⋯O hydrogen bonds are formed between HN(C=O)NH groups, building centrosymmetric dimers. These dimers are further linked through N—H⋯O(sulfonyl) contacts, forming chains in [100].

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“…The molecule is growing annually at the rate of 10-12% and numerous papers are devoted to its study. [8] The X-ray structure of 1 is known, [9,10] CSD-refcode SUVGUL (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

“…[11] Only the results of Ref. [10] were reported in the Cambridge Structural Database. [11] Note that, in the solid state, the N-H groups point to opposite directions (EZ isomer) and that the lone pair in the saturated 5,5-bicycle points toward the farthest N-H proton.…”

Section: Introductionmentioning

confidence: 99%

The behavior of Gliclazide in solution and in the solid state: a case of organic compound presenting a solid‐solution structure

María

Claramunt

Alkorta

et al. 2009

Magnetic Reson in Chemistry

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The structure of the hypoglycemic agent Gliclazide has been studied by (1)H, (13)C, and (15)N NMR in solution (CDCl(3) and DMSO-d(6)) and in the solid state. In the solid state, the compound crystallizes as an EZ isomer without dynamic properties. In CDCl(3) solution, the structure is still EZ but with a slow nitrogen inversion about the pyrrolidine nitrogen: two invertomers have been observed and characterized. In DMSO-d(6), the rate is faster and only averaged signals were observed. GIAO calculated absolute shieldings were used to confirm the nature of the observed species. In the solid state, Gliclazide presents the phenomenon of solid-solution with two disordered conformations present in the crystal at a 90:10 ratio.

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Gliclazide

Cited by 15 publications

References 0 publications

Isoenergetic Polymorphism: The Puzzle of Tolazamide as a Case Study

Isoenergetic Polymorphism: The Puzzle of Tolazamide as a Case Study

Gliclazide impurity F:N-[(perhydrocyclopenta[c]pyrrol-2-yl)aminocarbonyl]-o-toluenesulfonamide

The behavior of Gliclazide in solution and in the solid state: a case of organic compound presenting a solid‐solution structure

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