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Chemical Compound Review

SM-10661     (2R,5S)-3,5-dimethyl-2- pyridin-3-yl-1,3...

Synonyms: SM-12502, AC1L433Y, SM 10661, 130841-70-2, 158511-47-8, ...
This record was replaced with 178015.
 
 
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Disease relevance of (2R,5S)-3,5-dimethyl-2-pyridin-3-yl-thiazolidin-4-one

 

High impact information on (2R,5S)-3,5-dimethyl-2-pyridin-3-yl-thiazolidin-4-one

 

Chemical compound and disease context of (2R,5S)-3,5-dimethyl-2-pyridin-3-yl-thiazolidin-4-one

 

Biological context of (2R,5S)-3,5-dimethyl-2-pyridin-3-yl-thiazolidin-4-one

  • This study demonstrates a new deletional allele in the human CYP2A6 gene responsible for the poor metabolic phenotype of SM-12502 [5].
  • A new RFLP characterized by SacI and SphI was found to be due to the entire gene deletion of the three exons and was associated with the decreased metabolism of SM-12502 [5].
  • Thus, SM-12502 will be a useful tool in further research to analyze a human genetic polymorphism of CYP2A6 [6].
  • When SM-10661 was administered intravenously 2 min before ovalbumin challenge, bronchoconstriction was inhibited dose-dependently with an ID50 of 68 mg/kg [7].
  • This paper introduces one of our projects performed at Hokkaido University. During the course of pharmacokinetic studies of SM-12502, which was under development as an anti-platelet-activating factor agent, we found three individuals who showed a slow metabolic phenotype in its pharmacokinetics [8].
 

Anatomical context of (2R,5S)-3,5-dimethyl-2-pyridin-3-yl-thiazolidin-4-one

  • Microsomes from genetically engineered human B-lymphoblastoid cells expressing CYP2A6 metabolized SM-12502 to the S-oxide efficiently [6].
  • The effects of zymosan on the duodenum and liver were dose dependently inhibited by WEB-2086 and SM-12502 [9].
  • SM-10661 (30 mg/kg) administered orally 1 hr before the challenge significantly inhibited the increase in total cells, macrophages and eosinophils.(ABSTRACT TRUNCATED AT 250 WORDS)[10]
  • However, serum myeloperoxidase activity, a marker of neutrophil activation, was significantly suppressed by treatment with SM-12502 [3].
  • Coagulation abnormalities, TF activity, and focal necrosis of the hepatocytes were reduced by SM-12502 [11].
 

Associations of (2R,5S)-3,5-dimethyl-2-pyridin-3-yl-thiazolidin-4-one with other chemical compounds

 

Gene context of (2R,5S)-3,5-dimethyl-2-pyridin-3-yl-thiazolidin-4-one

 

Analytical, diagnostic and therapeutic context of (2R,5S)-3,5-dimethyl-2-pyridin-3-yl-thiazolidin-4-one

References

  1. Biological effect of orally active platelet-activating factor receptor antagonist SM-10661. Komuro, Y., Imanishi, N., Uchida, M., Morooka, S. Mol. Pharmacol. (1990) [Pubmed]
  2. A novel platelet activating factor antagonist, SM-12502, attenuates endotoxin-induced disseminated intravascular coagulation and acute pulmonary vascular injury by inhibiting TNF production in rats. Murakami, K., Okajima, K., Uchiba, M., Johno, M., Okabe, H., Takatsuki, K. Thromb. Haemost. (1996) [Pubmed]
  3. Platelet-activating factor antagonist, SM-12502, attenuates experimental glomerular thrombosis in rats. Hayashi, J., Hiromura, K., Koizumi, R., Shimizu, Y., Maezawa, A., Nojima, Y., Naruse, T. Nephron (2001) [Pubmed]
  4. A new deleted allele in the human cytochrome P450 2A6 (CYP2A6) gene found in individuals showing poor metabolic capacity to coumarin and (+)-cis-3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one hydrochloride (SM-12502). Nunoya, K., Yokoi, T., Kimura, K., Inoue, K., Kodama, T., Funayama, M., Nagashima, K., Funae, Y., Green, C., Kinoshita, M., Kamataki, T. Pharmacogenetics (1998) [Pubmed]
  5. A new CYP2A6 gene deletion responsible for the in vivo polymorphic metabolism of (+)-cis-3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one hydrochloride in humans. Nunoya, K.I., Yokoi, T., Kimura, K., Kainuma, T., Satoh, K., Kinoshita, M., Kamataki, T. J. Pharmacol. Exp. Ther. (1999) [Pubmed]
  6. (+)-cis-3,5-dimethyl-2-(3-pyridyl) thiazolidin-4-one hydrochloride (SM-12502) as a novel substrate for cytochrome P450 2A6 in human liver microsomes. Nunoya, K., Yokoi, Y., Kimura, K., Kodama, T., Funayama, M., Inoue, K., Nagashima, K., Funae, Y., Shimada, N., Green, C., Kamataki, T. J. Pharmacol. Exp. Ther. (1996) [Pubmed]
  7. Effect of the selective PAF antagonist SM-10661 on an asthmatic model. 1. Effect on passive anaphylactic bronchoconstriction in guinea pigs. Uchida, M., Imanishi, N., Sugasawa, T., Morooka, S. Lipids (1991) [Pubmed]
  8. Enticed into molecular toxicology. Kamataki, T. Yakugaku Zasshi (2006) [Pubmed]
  9. Platelet-activating factor and the vascular effects of zymosan in rats. Damas, J., Remacle-Volon, G., Bourdon, V. Eur. J. Pharmacol. (1993) [Pubmed]
  10. Effect of the selective PAF antagonist SM-10661 on an asthmatic model. 2. Effect on antigen-induced dual asthmatic response and infiltration of leukocytes into airways in actively sensitized conscious guinea pigs. Sugasawa, T., Imanishi, N., Morooka, S. Lipids (1991) [Pubmed]
  11. Possible role of platelet-activating factor in the in vivo expression of tissue factor in neutrophils. Todoroki, H., Higure, A., Okamoto, K., Okazaki, K., Nagafuchi, Y., Takeda, S., Katoh, H., Itoh, H., Ohsato, K., Nakamura, S. J. Surg. Res. (1998) [Pubmed]
  12. Effects of platelet activating factor receptor antagonists on intracellular platelet activating factor function in neutrophils. Koike, H., Imanishi, N., Natsume, Y., Morooka, S. Eur. J. Pharmacol. (1994) [Pubmed]
  13. Direct enantiomeric separation of platelet-activating factor receptor antagonist SM-10661 by ligand-exchange high-performance liquid chromatography with a copper (II) N,S-dioctyl-D-penicillamine complex. Okamoto, M., Ueda, Y., Takahashi, K., Nakazawa, H., Doi, T. Biosci. Biotechnol. Biochem. (1995) [Pubmed]
  14. Genetic polymorphism of CYP2A6 as one of the potential determinants of tobacco-related cancer risk. Kamataki, T., Fujieda, M., Kiyotani, K., Iwano, S., Kunitoh, H. Biochem. Biophys. Res. Commun. (2005) [Pubmed]
  15. Inhibition of leukotriene formation and IL-8 release by the paf-receptor antagonist SM-12502. Hilger, R.A., Köller, M., König, W. Inflammation (1996) [Pubmed]
  16. Effect of a selective PAF antagonist SM-10661 ((+/-)-cis-3,5-dimethyl-2-(3-pyridyl)thiazolidin-4-one HCl) on experimental disseminated intravascular coagulation (DIC). Imanishi, N., Komuro, Y., Morooka, S. Lipids (1991) [Pubmed]
  17. S-oxidation of (+)-cis-3,5-dimethyl-2-(3-pyridyl)-thiazolidin-4-one hydrochloride by rat hepatic flavin-containing monooxygenase 1 expressed in yeast. Nunoya, K., Yokoi, T., Itoh, K., Itoh, S., Kimura, K., Kamataki, T. Xenobiotica (1995) [Pubmed]
 
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