Piretanide

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Piretanide
Piretanide structure.svg
Systematic (IUPAC) name
3-(aminosulfonyl)-4-phenoxy-5-pyrrolidin-1-ylbenzoic acid
Clinical data
Trade names Arelix, Eurelix, Tauliz
AHFS/Drugs.com International Drug Names
Legal status
  • ℞ (Prescription only)
Routes of
administration
Oral
Pharmacokinetic data
Bioavailability ~90%[1]
Protein binding 96%
Metabolism not identified
Excretion Urine (60%), feces (40%)
Identifiers
CAS Number 55837-27-9 YesY
ATC code C03CA03 (WHO)
PubChem CID: 4849
IUPHAR/BPS 4742
DrugBank DB02925 N
ChemSpider 4683 N
UNII DQ6KK6GV93 YesY
KEGG D01634 YesY
Chemical data
Formula C17H18N2O5S
Molecular mass 362.40 g/mol
 NYesY (what is this?)  (verify)

Piretanide (INN, trade names Arelix, Eurelix, Tauliz) has been synthesized in 1973 at Hoechst AG (Germany) as a loop diuretic[2] compound by using a then-new method for introducing cyclic amine residues in an aromatic nucleus in the presence of other aromatically bonded functional groups. Studies of piretanide in rats and dogs in comparison with other high-ceiling diuretics such as furosemide and bumetanide found a more suitable dose/response rate (regression line) and a more favourable sodium/potassium excretion ratio. These findings led eventually to clinical studies in man and finally to the introduction as a saluretic and antihypertensive[3] medication in Germany, France, Italy and other countries.

References

  1. Mutschler, Edited by Rainer F. Greger, H. Knauf, E. Mutschler (1995). Diuretics. Handbook of Experimental Pharmacology (Том 117). Berlin, Heidelberg: Springer Science & Business Media, 2012. p. 517. ISBN 364279565X. <templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  2. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  3. Haberfeld, H, ed. (2009). Austria-Codex (in German) (2009/2010 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 3-85200-196-X. <templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  • W.Merkel, D.Bormann, D.Mania, R.Muschaweck and M.Hropot, Eur. J. Med. Chem.-Chim.Ther. 11,399 (1976).
  • W.Merkel, D.Mania and D.Bormann, Liebigs Ann. Chem. 461 (1979).