Piretanide

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 448119456

| IUPAC_name = 3-(aminosulfonyl)-4-phenoxy-5-pyrrolidin-1-ylbenzoic acid

| image = Piretanide structure.svg

| image_class = skin-invert-image

| tradename = Arelix, Eurelix, Tauliz, others

| Drugs.com = {{drugs.com|international|piretanide}}

| pregnancy_AU =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_EU = Rx-only

| legal_EU_comment = {{cite web|url=https://www.ema.europa.eu/documents/psusa/piretanide-list-nationally-authorised-medicinal-products-psusa/00002433/202110_en.pdf|title=List of nationally authorised medicinal products : Active substance: piretanide: Procedure no.: PSUSA/00002433/202110|website=Ema.europa.eu|access-date=28 June 2022}}

| legal_status = Rx-only

| routes_of_administration = By mouth

| bioavailability = ~90%{{cite book| vauthors = Mutschler E | veditors = Greger RF, Knauf H, Mutschler E | title = Diuretics | series = Handbook of Experimental Pharmacology | volume = 117 |date=1995 |publisher=Springer Science & Business Media |location=Berlin, Heidelberg|isbn=978-3642795657|page=517}}

| protein_bound = 96%

| metabolism = not identified

| elimination_half-life =

| excretion = Urine (60%), feces (40%)

| IUPHAR_ligand = 4742

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 55837-27-9

| ATC_prefix = C03

| ATC_suffix = CA03

| ATC_supplemental =

| PubChem = 4849

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB02925

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = DQ6KK6GV93

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D01634

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4683

| chemical_formula =

| C=17 | H=18 | N=2 | O=5 | S=1

| smiles = NS(=O)(=O)c1c(Oc2ccccc2)c(N3CCCC3)cc(c1)C(=O)O

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = UJEWTUDSLQGTOA-UHFFFAOYSA-N

}}

Piretanide is a loop diuretic{{cite journal | vauthors = Musini VM, Rezapour P, Wright JM, Bassett K, Jauca CD | title = Blood pressure-lowering efficacy of loop diuretics for primary hypertension | journal = The Cochrane Database of Systematic Reviews | volume = 2015 | issue = 5 | pages = CD003825 | date = May 2015 | pmid = 26000442 | pmc = 7156893 | doi = 10.1002/14651858.CD003825.pub4 }} 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{{cite book|title=Austria-Codex| veditors = Haberfeld H|publisher=Österreichischer Apothekerverlag|location=Vienna|year=2009|edition=2009/2010|isbn=978-3-85200-196-8|language=German}} medication in Germany, France, Italy and other countries.

It was made in 1973, patented in 1974, and approved for medical use in 1981.{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=458 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA458 |language=en}}