Metabolism of 4-[1-(2-fluoro-4-biphenylyl)ethyl]-2-methylaminothiazole (SM-8849) in rats

European Journal of Drug Metabolism and Pharmacokinetics

Volumn 22, Issue 1, 1997, Pages 25-33

  Yabuki, M ^a   Shimakura, J ^a   Ito, M ^a   Kanamaru, H ^a   Iba, K ^b   Nakatsuka, I ^a  

^a SUMITOMO CHEMICAL CO LTD   (Japan)

^b DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

Author keywords

Immunomodulator; LC MS MS; Metabolism; Rat; SM 8849; Thiazole

Indexed keywords

4 [1 (2 FLUORO 4 BIPHENYLYL)ETHYL] 2 METHYLAMINOTHIAZOLE; GLUCURONIDE; IMMUNOMODULATING AGENT; SULFATE;

ANIMAL EXPERIMENT; ARTICLE; CHROMATOGRAPHY; CONTROLLED STUDY; DEMETHYLATION; DRUG BILE LEVEL; DRUG CONJUGATION; DRUG HYDROXYLATION; DRUG METABOLISM; DRUG URINE LEVEL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; MALE; MASS SPECTROMETRY; METHYLATION; NONHUMAN; ORAL DRUG ADMINISTRATION; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; THIN LAYER CHROMATOGRAPHY;

EID: 0030942692     PISSN: 03787966     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF03189781     Document Type: Article

References (17)

1. Abe C., Nishikaku F., Koga Y. (1991): Effects of SM-8849 on spontaneous arthritis in MRL/1 mice and type II collagen-induced arthritis in DBA/1J mice. Int. J. Immunother., 7, 1-8.
2. Nishikaku Y., Koga Y. (1991): Alteration in progression of murine autoimmune disease by treatment with a novel immunomodulator, SM-8849. Int. J. Immunopharmacol., 13, 445-454.
3. Nishikaku F., Koga Y. (1993): Suppression of murine collagen-induced arthritis by treatment with a novel thiazole derivative, SM-8849. Immunopharmacology, 25, 65-74.
4. Nishikaku F., Nakamura K., Kashiwazaki S., Koga Y. (1994): Prevention of spontaneous polyarthritis in NBZ/KN mice by treatment with a novel thiazole derivative, SM-8849. Drugs Exp. Clin. Res., 20, 85-92.
5. Mico B.A., Swagzdis J.E., Federowicz D.A., Straub K. (1986): Functional group metabolism of dopamine-2 agonists: conversion of 4-(2-di-n-propylaminoethyl)-2-(3H)-indolone to 4-(2-di-n-propylaminoethyl)-7-hydroxy-2-(3H)-indolone. J. Pharm. Sci., 75, 929-933.
6. Rudwicz P., Straub K.M. (1986): Rapid structure elucidation of catecholamine conjugates with tandem mass spectrometry. Anal. Chem., 58, 2928-2934.
7. Brashear W.T., Kuhnert B.R., Wei R. (1990): Structural determination of the conjugated metabolites of ritodrine. Drug Metab. Dispos., 18, 488-493.
8. Jackson C.J., Hubbard J.W., McKay G., Cooper J.K., Hawes E.M., Midha K.K. (1991): Identification of phase I and phase II metabolites of fluphenazine in rat bile: intact glucuronide and sulfate conjugates. Drug Metab. Dispos., 19, 188-193.
9. Yabuki M., Mine T., Iba K., Nakatsuka I., Yoshitake A. (1993): Metabolism of a tetrahydroaminoacridine derivative (SM-10888) in rat: structural analysis of an N-glucuronide of SM-10888 and an O-glucuronide of hydroxylated SM-10888 by FAB-MS/MS. Xenobiotica, 12, 1367-1375.
10. Risdall P.C., Adams S.S., Crampton E.L., Marchant B. (1978): The disposition and metabolism of flurbiprofen in several species including man. Xenobiotica, 8, 691-704.
11. Maguire J.H., Kraus B.L., Buttler T.C., Dudly K.H. (1981): Stereochemical aspects of the metabolism of 5-ethyl-5-phenylhydantoin (NILVANOL) in the dog. Drug Metab. Dispos., 9, 393-401.
12. Andersen J.V., Dalgaard L., Hansen S.H. (1989): Enzymic synthesis of two glucuronides of the hydroxyl oxazole GABA-agonist, THIP, and the in vivo glucuronidation of THIP in rat. Xenobiotica, 19, 1399-1406.
13. Chatfield D.H., Hunter W.H. (1973): The metabolism of acetamidothiazoles in the rat: 2-acetamido-, 2-acetamido-4-methyl-and 2-acetamido-4-phenyl-thiazole. Biochem. J., 134, 869-878.
14. Chatfield D.H., Hunter W.H. (1973): The metabolism of acetamidothiazoles in the rat: 2-acetamido-4-chloromethylthiazole. Biochem. J., 134, 879-884.
15. Mutlib A.E., Chui Y.C., Young L.M., Abbott F.S. (1992): Characterization of metabolites of xylazine produced in vivo and in vitro by LC/MS/MS and GC/MS. Drug Metab. Dispos., 20, 840-848.
16. Mizutani T., Yoshida K., Kawazoe S. (1994): Formation of toxic metabolites from thiabendazole and other thiazoles in mice: identification of thioamides as ring cleavage products. Drug Metab. Dispos., 22, 750-755.
17. Liberti P., Stanbury J.B. (1971): The pharmacology of substances affecting the thyroid gland. Annu. Rev. Pharmacol., 11, 113-142.