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	80343-63-1;
PubChem CID	71763;
ChemSpider	64802;
UNII	56B0591Y76;
KEGG	D05939;
CompTox Dashboard (EPA)	DTXSID50230254 ;
Chemical and physical data
Formula	C20H31N5O3S
Molar mass	421.56 g·mol−1
3D model (JSmol)	Interactive image;
	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

References

^ "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.
^ "Drug Profile: Sufotidine". AdisInsight. Springer International Publishing AG. Retrieved 12 January 2016.
^ "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.
^ 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.
^ 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.
^ Ganellin CR, Triggle DJ, eds. (1999). Dictionary of Pharmacological Agents (1st ed.). London: Chapman & Hall. ISBN 9780412466304.
^ Lawton G, Witty DR, eds. (2011). Progress in Medicinal Chemistry. Vol. 50 (1st ed.). London: Academic. p. 36. ISBN 978-0-12-381290-2.

[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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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	80343-63-1
PubChem CID	71763
ChemSpider	64802
UNII	56B0591Y76
KEGG	D05939
CompTox Dashboard (EPA)	DTXSID50230254
Chemical and physical data
Formula	C₂₀H₃₁N₅O₃S
Molar mass	421.56 g·mol⁻¹
3D model (JSmol)	Interactive image
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

Synthesis

See also

References