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  • Interaction of methimazole with I2: X-ray crystal structure of the charge transfer complex methimazole-I2. implications for the mechanism of action of methimazole-based antithyroid drugs.

Interaction of methimazole with I2: X-ray crystal structure of the charge transfer complex methimazole-I2. implications for the mechanism of action of methimazole-based antithyroid drugs.

Journal of medicinal chemistry (2008-06-06)
Francesco Isaia, M Carla Aragoni, Massimiliano Arca, Francesco Demartin, Francesco A Devillanova, Giovanni Floris, Alessandra Garau, Michael B Hursthouse, Vito Lippolis, Rosaria Medda, Fabio Oppo, Marilena Pira, Gaetano Verani
ABSTRACT

The antithyroid drug methimazole (MMI) reacts with molecular iodine to form, in a multistep process, 1-methylimidazole as final product. In this process, the charge transfer complex MMI-I 2 and the ionic disulfide [(C 4H 6N 2S-) 2] (2+) ( 1, dication MMI disulfide) have been isolated and their X-ray crystal structures solved. Dication MMI disulfide perchlorate acts effectively both in reducing I 2 to I (-) ions and in showing antioxidant properties in inactivating the enzyme lactoperoxidase compound I.

MATERIALS
Product Number
Brand
Product Description

Supelco
Methimazole, analytical standard
Sigma-Aldrich
2-Mercapto-1-methylimidazole, ≥99%