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Gliclazide impurity F: N-[(perhydro-cyclo-penta-[c]pyrrol-2-yl)amino-carbon-yl]-o-toluene-sulfonamide.

ABSTRACT: The title compound, C(15)H(21)N(3)O(3)S, is known to be an impurity of gliclazide [systematic name: N-(hexa-hydro-1H-cyclopenta[c]pyrrol-2-ylcarbamo-yl)-4-methyl-benzene-sulfonamide], a sul-fonyl-urea anti-diabetic drug. Gliclazide has a p-tolyl group substituting the sulfonamide functionality, while the title mol-ecule 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(sulfon-yl) contacts, forming chains in [100].

SUBMITTER: Wu D

PROVIDER: S-EPMC3275201 | biostudies-literature | 2012 Feb

REPOSITORIES: biostudies-literature

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Gliclazide impurity F: N-[(perhydro-cyclo-penta-[c]pyrrol-2-yl)amino-carbon-yl]-o-toluene-sulfonamide.

Wu Di D Wang Xueyuan X Pang Dongying D Su Wei W Sun Yan Y

Acta crystallographica. Section E, Structure reports online 20120118 Pt 2

The title compound, C(15)H(21)N(3)O(3)S, is known to be an impurity of gliclazide [systematic name: N-(hexa-hydro-1H-cyclopenta[c]pyrrol-2-ylcarbamo-yl)-4-methyl-benzene-sulfonamide], a sul-fonyl-urea anti-diabetic drug. Gliclazide has a p-tolyl group substituting the sulfonamide functionality, while the title mol-ecule 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 centros ...[more]

PMID: 22347057

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