Piretanide

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Piretanide
Piretanide structure.svg
Clinical data
Trade names Arelix, Eurelix, Tauliz
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability ~90%[1]
Protein binding 96%
Metabolism not identified
Excretion Urine (60%), feces (40%)
Identifiers
CAS Number
  • 55837-27-9 ☑Y
PubChem CID
  • 4849
IUPHAR/BPS
  • 4742
DrugBank
  • DB02925 ☒N
ChemSpider
  • 4683 ☒N
UNII
  • DQ6KK6GV93
KEGG
  • D01634 ☑Y
ECHA InfoCard 100.054.394
Chemical and physical data
Formula C17H18N2O5S
Molar mass 362.40 g/mol g·mol−1
3D model (JSmol)
  • Interactive image
 ☒N☑Y (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][needs update] 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.CS1 maint: Extra text: authors list (link)
  2. ^ Musini VM, Rezapour P, Wright JM, Bassett K, Jauca CD (August 2012). Musini VM, ed. "Blood pressure lowering efficacy of loop diuretics for primary hypertension". The Cochrane Database of Systematic Reviews (8): CD003825. doi:10.1002/14651858.CD003825.pub3. PMID 22895937.
  3. ^ Haberfeld, H, ed. (2009). Austria-Codex (in German) (2009/2010 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 3-85200-196-X.

Further reading

  • Merkel W, Bormann D, Mania D, Muschaweck R, Hropot M (1976). "Piretanide (HOE118): A new high-ceiling sali-diuretic". European Journal of Medicinal Chemistry. 11: 399.
  • Merkel W, Mania D, Bormann D (1979). "Selektive Reduktion von Imiden mit funktionellen Gruppen" [Selective reduction of imides in the presence of other function groups]. Liebigs Annalen der Chemie (in German). 4: 461–9. doi:10.1002/jlac.197919790406.
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