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Sufotidine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Sufotidine
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
PubChemCID
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC20H31N5O3S
Molar mass421.56 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,[1]USAN, codenamed AH25352) is a long-acting competitiveH2 receptorantagonist which was under development as anantiulcerant by Glaxo (nowGlaxoSmithKline).[2] It was planned to be a follow-up compound toranitidine (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 theproton pump inhibitoromeprazole.[5] Its development was terminated in 1989[6] fromphase III clinical trials based on the appearance of carcinoid tumors in long-term toxicity testing in rodents.[7]

Synthesis

[edit]

See also

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

References

[edit]
  1. ^"International Nonproprietary Names for Pharmaceutical Substances. Supplement toWHO Chronicle, 1986, Vol. 40, No. 6. Recommended International Nonproprietary Names (Rec. INN): List 26"(PDF). World Health Organization. p. 9. Retrieved12 January 2016.
  2. ^"Drug Profile: Sufotidine".AdisInsight. Springer International Publishing AG. Retrieved12 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. Retrieved12 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.
H2 antagonists ("-tidine")
Prostaglandins (E)/
analogues ("-prost-")
Proton-pump inhibitors
("-prazole")
Potassium-competitive
acid blockers ("-prazan")
Others
Combinations
H1
Agonists
Antagonists
H2
Agonists
Antagonists
H3
Agonists
Antagonists
H4
Agonists
Antagonists
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