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Abandoned drugs
Tibric acid
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    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
    EC Number
    • 253-344-0
    KEGG
    PubChem CID
    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. 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. 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.

    Synthesis

    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.


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