Piretanide

Piretanide is a loop diuretic[3] 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 studies in man and finally to the introduction as a saluretic and antihypertensive[4] medication in Germany, France, Italy and other countries.

Piretanide
Clinical data
Trade namesArelix, Eurelix, Tauliz, others
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • EU: Rx-only [1]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability~90%[2]
Protein binding96%
Metabolismnot identified
ExcretionUrine (60%), feces (40%)
Identifiers
IUPAC name
  • 3-(aminosulfonyl)-4-phenoxy-5-pyrrolidin-1-ylbenzoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.054.394
Chemical and physical data
FormulaC17H18N2O5S
Molar mass362.40 g·mol−1
3D model (JSmol)
SMILES
  • NS(=O)(=O)c1c(Oc2ccccc2)c(N3CCCC3)cc(c1)C(=O)O
InChI
  • InChI=1S/C17H18N2O5S/c18-25(22,23)15-11-12(17(20)21)10-14(19-8-4-5-9-19)16(15)24-13-6-2-1-3-7-13/h1-3,6-7,10-11H,4-5,8-9H2,(H,20,21)(H2,18,22,23) N
  • Key:UJEWTUDSLQGTOA-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

It was made in 1973, patented in 1974, and approved for medical use in 1981.[5]

Brand names

Brand names include Arelix, Eurelix, Tauliz.

References
  1. "List of nationally authorised medicinal products : Active substance: piretanide: Procedure no.: PSUSA/00002433/202110" (PDF). Ema.europa.eu. Retrieved 28 June 2022.
  2. Mutschler (1995). Rainer F. Greger; H. Knauf; E. Mutschler (eds.). Diuretics. Berlin, Heidelberg: Springer Science & Business Media. p. 517. ISBN 978-3642795657.
  3. Musini, Vijaya M.; Rezapour, Pouria; Wright, James M.; Bassett, Ken; Jauca, Ciprian D. (2015-05-22). "Blood pressure-lowering efficacy of loop diuretics for primary hypertension". The Cochrane Database of Systematic Reviews (5): CD003825. doi:10.1002/14651858.CD003825.pub4. ISSN 1469-493X. PMC 7156893. PMID 26000442.
  4. Haberfeld, H, ed. (2009). Austria-Codex (in German) (2009/2010 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 978-3-85200-196-8.
  5. Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 458. ISBN 9783527607495.

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). 1979 (4): 461–9. doi:10.1002/jlac.197919790406.


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