Sufotidine

Sufotidine
Clinical data
Routes of
administration		Oral
ATC code
  • None
Legal status
Legal status
  • Development terminated
Identifiers
IUPAC name
  • 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
FormulaC20H31N5O3S
Molar mass421.56 g·mol−1
3D model (JSmol)
SMILES
  • CN1C(=NC(=N1)CS(=O)(=O)C)NCCCOC2=CC=CC(=C2)CN3CCCCC3
InChI
  • 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

See also

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

References

  1. ↑ "International Nonproprietary Names for Pharmaceutical Substances. Supplement to WHO Chronicle, 1986, Vol. 40, No. 6. Recommended International Nonproprietary Names (Rec. INN): List 26" (PDF). World Health Organization. p. 9. Retrieved 12 January 2016.
  2. ↑ "Drug Profile: Sufotidine". AdisInsight. Springer International Publishing AG. Retrieved 12 January 2016.
  3. ↑ "Glaxo Plans to Follow Up Zantac with Long-acting Sufotidine; H2 Antagonist Is One of Seven Drugs Targeted for Worldwide Marketing Applications in 1988–90". Pharma & MedTech Business Intelligence. Informa Business Intelligence, Inc., an Informa Company. November 30, 1987. Retrieved 12 January 2016.
  4. ↑ Smith JT, Pounder RE (March 1990). "Sufotidine 600 mg bd virtually eliminates 24 hour intragastric acidity in duodenal ulcer subjects". Gut. 31 (3): 291–3. doi:10.1136/gut.31.3.291. PMC 1378269. PMID 1969833.
  5. ↑ Fiorucci S, Santucci L, Farroni F, Pelli MA, Morelli A (October 1989). "Effect of omeprazole on gastroesophageal reflux in Barrett's esophagus". The American Journal of Gastroenterology. 84 (10): 1263–7. PMID 2801676.
  6. ↑ Ganellin CR, Triggle DJ, eds. (1999). Dictionary of Pharmacological Agents (1st ed.). London: Chapman & Hall. ISBN 9780412466304.
  7. ↑ Lawton G, Witty DR, eds. (2011). Progress in Medicinal Chemistry. Vol. 50 (1st ed.). London: Academic. p. 36. ISBN 978-0-12-381290-2.
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