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Abandoned drugs
Sufotidine
Другие языки:

    Sufotidine

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    Sufotidine
    Sufotidine.svg
    Clinical data
    Routes of
    administration    		 Oral
    ATC code
    • None
    Legal status
    Legal status
    • Development terminated
    Identifiers
    • 2-methyl-5-(methylsulfonylmethyl)-N-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-1,2,4-triazol-3-amine
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    KEGG
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C20H31N5O3S
    Molar mass 421.56 g·mol−1
    3D model (JSmol)
    • CN1C(=NC(=N1)CS(=O)(=O)C)NCCCOC2=CC=CC(=C2)CN3CCCCC3
    • InChI=1S/C20H31N5O3S/c1-24-20(22-19(23-24)16-29(2,26)27)21-10-7-13-28-18-9-6-8-17(14-18)15-25-11-4-3-5-12-25/h6,8-9,14H,3-5,7,10-13,15-16H2,1-2H3,(H,21,22,23)
    • Key:JEYKZWRXDALMNG-UHFFFAOYSA-N

    Sufotidine (INN,USAN, codenamed AH25352) is a long-acting competitive H2 receptor antagonist which was under development as an antiulcerant by Glaxo (now GlaxoSmithKline). It was planned to be a follow-up compound to ranitidine (Zantac). When taken in doses of 600 mg twice daily it induced virtually 24-hour gastric anacidity thus closely resembling the antisecretory effect of the proton pump inhibitor omeprazole. Its development was terminated in 1989 from phase III clinical trials based on the appearance of carcinoid tumors in long-term toxicity testing in rodents.

    Synthesis

    Sufotidine synthesis.png

    See also

    • Lavoltidine (previously known as loxtidine) — a similar compound in which methylsulfone group is replaced with hydroxyl

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