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  • Title: [The synthesis, analysis, stability and biotransformation of N-(3-methylphenyl)-N'-cyanobenzamidine and analogues (author's transl)].
    Author: Pfeifer S, Barnikow G, Schulz M, Kraft R, Fritsche E.
    Journal: Pharmazie; 1981 Nov; 36(11):757-63. PubMed ID: 7323123.
    Abstract:
    The antivirally active N-(3-methylphenyl)-N'-cyanobenzamidine (1) and some of its analogues were synthetized by the reaction of the ethyl ester of N-cyanobenzimidic acid with the corresponding arylamines. The analytical profile of 1 and of some of its analogues, which is needed for stability and biotransformation studies, was established by means of the following techniques: solubility determination, TLC, UV, IR and MS. When 1 is heated with methanolic HCl and NaOH (0.5 mol/l) for 1 h, several hydrolysis products are formed: m-toluidine, benzoic acid, benzoic acid 3-toluidide, N-(3-methylphenyl)benzamidine, N-(3-methylphenyl)-N'-carboxamidobenzamidine, benzoylurea, However, 1 is fairly stable under physiological conditions so biotransformation studies are not affected. After oral application of 1 to rats, the 3-hydroxymethyl and the 3-methyl-5-hydroxy compound as well as its glucuronide and sulphate conjugate were detected in the urine. The faeces contained considerable amounts of unchanged 1 (incomplete absorption).
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