Piretanide

Summary

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
  • 3-(aminosulfonyl)-4-phenoxy-5-pyrrolidin-1-ylbenzoic acid
CAS Number
  • 55837-27-9 checkY
PubChem CID
  • 4849
IUPHAR/BPS
  • 4742
DrugBank
  • DB02925 ☒N
ChemSpider
  • 4683 ☒N
UNII
  • DQ6KK6GV93
KEGG
  • D01634 checkY
CompTox Dashboard (EPA)
  • DTXSID2023488 Edit this at Wikidata
ECHA InfoCard100.054.394 Edit this at Wikidata
Chemical and physical data
FormulaC17H18N2O5S
Molar mass362.40 g·mol−1
3D model (JSmol)
  • Interactive image
  • NS(=O)(=O)c1c(Oc2ccccc2)c(N3CCCC3)cc(c1)C(=O)O
  • 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
 ☒NcheckY (what is this?)  (verify)

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

Brand names edit

Brand names include Arelix, Eurelix, Tauliz.

References edit

  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 E (1995). Greger RF, Knauf H, Mutschler E (eds.). Diuretics. Handbook of Experimental Pharmacology. Vol. 117. Berlin, Heidelberg: Springer Science & Business Media. p. 517. ISBN 978-3642795657.
  3. ^ Musini VM, Rezapour P, Wright JM, Bassett K, Jauca CD (May 2015). "Blood pressure-lowering efficacy of loop diuretics for primary hypertension". The Cochrane Database of Systematic Reviews. 2015 (5): CD003825. doi:10.1002/14651858.CD003825.pub4. 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 J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 458. ISBN 9783527607495.

Further reading edit

  • 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.