Tibric acid

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Tibric acid
Tibric acid.svg
Names
Preferred IUPAC name
2-Chloro-5-[(3R,5S)-3,5-dimethylpiperidine-1-sulfonyl]benzoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.048.479 Edit this at Wikidata
EC Number
  • 253-344-0
KEGG
UNII
  • InChI=1S/C14H18ClNO4S/c1-9-5-10(2)8-16(7-9)21(19,20)11-3-4-13(15)12(6-11)14(17)18/h3-4,6,9-10H,5,7-8H2,1-2H3,(H,17,18)/t9-,10+
    Key: IFXSWTIWFGIXQO-AOOOYVTPSA-N
  • C[C@@H]1C[C@@H](CN(C1)S(=O)(=O)C2=CC(=C(C=C2)Cl)C(=O)O)C
Properties
C14H18ClNO4S
Molar mass 331.81 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tibric acid is a sulfamylbenzoic acid that acts as a hypolipidemic agent.[1] Although it was found to be more powerful than clofibrate in lowering lipid levels, it was found to cause liver cancer in mice and rats, and so was not introduced as a human drug.[2] In rats it causes an increase in peroxisomes, and liver enlargement, and then liver cancer. However the peroxisome changes do not occur in humans, and it is not likely to cause liver cancer in humans.[3][4]

Synthesis[edit]

Tibric acid can be made in a multi-step process. Firstly 2-chlorobenzoic acid is reacted with chlorosulfonic acid to add chlorosulfonate group in the 5- position. This reacts with 3,5-dimethylpiperidine to yield tibric acid.[5]

References[edit]

  1. ^ Bencze, W. L.; Kritchevsky, D.; Dempsey, M. E.; Eisenberg, S.; Felts, J. M.; Frantz, I. D.; Hess, R.; Levy, R. I.; Miettinen, T. A.; Rudel, L. L.; Sodhi, H. S.; Stäubli, W.; Zemplényi, T. (2012). Hypolipidemic Agents. Progress in Drug Research. Fortschritte der Arzneimittelforschung. Progres des Recherches Pharmaceutiques. Vol. 13. Springer Science & Business Media. pp. 217–292. doi:10.1007/978-3-0348-7068-9_5. ISBN 9783642661907. PMID 4982663.
  2. ^ Lalloyer, F.; Staels, B. (14 April 2010). "Fibrates, Glitazones, and Peroxisome Proliferator-Activated Receptors". Arteriosclerosis, Thrombosis, and Vascular Biology. 30 (5): 894–899. doi:10.1161/ATVBAHA.108.179689. PMC 2997800. PMID 20393155.
  3. ^ Cohen, A.J.; Grasso, P. (January 1981). "Review of the hepatic response to hypolipidaemic drugs in rodents and assessment of its toxicological significance to man". Food and Cosmetics Toxicology. 19 (5): 585–605. doi:10.1016/0015-6264(81)90509-5. PMID 7030887.
  4. ^ Lai, David Y. (26 December 2004). "Rodent Carcinogenicity of Peroxisome Proliferators and Issues on Human Relevance". Journal of Environmental Science and Health, Part C. 22 (1): 37–55. doi:10.1081/GNC-120038005. PMID 15845221. S2CID 23950095.
  5. ^ Lednicer, Daniel; Mitscher, Lester A.; Georg, Gunda I. (1977). The Organic Chemistry of Drug Synthesis. John Wiley & Sons. p. 87. ISBN 9780471043928.