Fig. 1. Structure of [methyl-14c]zonisamide
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1 Key words : Zonisamide, Metabolism, Plasma, Erythrocytes, Preputial gland, Urine, Bile, Rat, Dog, Monkey Metabolism of ["Clzonisamide in rats, dogs and monkeys Katashi MATSUMOTO, Koji YOSHIDA, Toshihiko Fu.ni, Hideo FURUKAWA, Hisashi MIYAZAKI and Masahisa HASHIMOTO Research Laboratories, Dainippon Pharmaceutical Co. Ltd., Enoki 33-94, Suita, Osaka 564, Japan
2 Fig. 1. Structure of [methyl-14c]zonisamide
3 Fig. 2. Typical TLC-radiochromatograms of metabolites in plasma (a), erythrocytes (b) and preputial gland (c) after oral administration of [14C]zonisamide in rats (20 mg/kg) Solvent system : chloroform/methanol/28 % am monia water (50/20/1) O : origin, F : solvent front. Closed circles indi cate the position of authentic references after development. UD : unchanged zonisamide, C carboxylic acid.
4 Fig. 3. Typical TLC-radiochromatograms of urinary metabolites after oral administra tion of [14C] zonisamide in animals (20 mg/kg) A : acetylated-zonisamide See also the legend of Fig. 2. Table I. Composition of urinary metabolites after administration of [14C]zonisamide in some animal species Values are means of n animals (±S.E.). Empty columns indicate no determinations. : not detected n : Number of animals UD : Zonisamide, MI : Zonisamide glucuronide, MIT : Conjugate of N-O cleaved com pound, Rat MIT is the fraction containing unknown metabolite(s). MIII : Acetylated-zonisamide, MTV Glucuronide of hydroxylated-zonisamide, MV : Carboxylic acid. Dog MV is a glucuronide. * : Previously idertified by TLC/MS in rat urine'). ** : p<0.01, compared with single administration
5 Fig. 4. A typical TLC-radiochromatogram of bile metabolites after oral administra tion of [14C]zonisamide in rat (20mg/ kg). See also the legend of Fig. 2. Fig. 5. Metabolic pathways of zonisamide in animals
6 Fig. 6. A typical TLC radiochromatogram profile of the extract from dog urine treated with Q-glucuronidase after pretreatment with ethyl acetate (a) and mass spectra of metabolite PI, PII and Pill (b) N : N-O cleaved compound See also the legend of Fig. 2.
7 Fig. 7. A typical TLC-radiochromatogram profile of intact monkey urine (a) and mass spectra of metabolite P'I and P'II (b). See also the legend of Fig. 2 and 3.
8 1) Masuda, Y., Karasawa, T., Shiraishi, Y., Hori, M., Yoshida, K. and Shimizu, M.: 3-Sulfamoylmethyl-1,2-benzisoxazole, a new type of anticonvulsant drug. Arzneim.-Forsch., 30(I) : (1980). 3) Matsumoto, K., Miyazaki, H., Fujii, T., Kagemoto, A., Maeda, T. and Hashimoto, M. : Absorption, distribution and excretion of 3-(sulfamoyl-[14C] methyl)-1,2 benzisoxazole (AD-810) in rats, dogs and monkeys and of AD-810 in men. Arzneim.-Forsch., 33(11) : (1983). 5) Uno, H. and Kurokawa, M. : Studies on 3-substituted 1,2-benzisoxazole deriva tives. VI. Synthesis of 3-(sulfamoylmethyl)-1,2-benzisoxazole and their anticon vulsant activities. J. Med. Chem., 22 : (1979). 6) Casini, G., Gualtieti, F. and Stein, M.L. : On 1,2-benzisoxazole-3-acetic acid and 3-methyl-1,2-benzisoxazole : a restatement. J. Heterocyclic Chem., 6 : (1969). 7) Uno, H. and Kurokawa, M. : Studies on 3-substituted 1,2-benzisoxazole deriva tives. VII. Catalytic reduction of 3-sulfa moylmethyl-1,2-benzisoxazole and reac tions of the resulting products. Chem. Pharm. Bull., 30 : (1981). 8) Miyazaki, H., Matsunaga, Y., Nambu, K., Oh-e, Y., Yoshida, K. and Hashimoto, M. : Disposition and metabolism of [14C]-haloperidol in rats. Arzneim.-Forsch. 360): (1986).
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