Sufotidine

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Sufotidine
Sufotidine.svg
Systematic (IUPAC) name
2-methyl-5-(methylsulfonylmethyl)-N-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]-1,2,4-triazol-3-amine
Clinical data
Legal status
  • Development terminated
Routes of
administration		 Oral
Identifiers
CAS Number 80343-63-1
ATC code None
PubChem CID: 71763
ChemSpider 64802
UNII 56B0591Y76
KEGG D05939
Chemical data
Formula C20H31N5O3S
Molecular mass 421.556 g/mol
  • 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,[1] USAN, codenamed AH25352) is a long-acting competitive H2 receptor antagonist which was under development as an antiulcerant by Glaxo (now GlaxoSmithKline).[2] It was planned to be a follow-up compound to ranitidine (Zantac).[3] When taken in doses of 600 mg twice daily it induced virtually 24-hour gastric anacidity[4] thus closely resembling the antisecretory effect of the proton pump inhibitor omeprazole.[5] Its development was terminated in 1989[6] from phase III clinical trials based on the appearance of carcinoid tumors in long-term toxicity testing in rodents.[7]

Synthesis

Sufotidine synthesis.png

See also

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

References

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