Piretanide: Difference between revisions

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{{Drugbox

| Verifiedfields = changed

| verifiedrevid = ~~443244645~~

| verifiedrevid = 448119456

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

| image = Piretanide.~~png~~

| image = Piretanide structure.svg

| tradename =

| tradename = Arelix, Eurelix, Tauliz, others

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

| pregnancy_AU =

⚫

| pregnancy_category =

| pregnancy_US =

⚫

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_EU = Rx-only

| legal_EU_comment = <ref>{{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}}</ref>

| legal_status = Rx-only

| routes_of_administration = Oral

| routes_of_administration = [[Oral administration|By mouth]]

| bioavailability = ~90%<ref>{{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}}</ref>

| bioavailability =

| protein_bound =

| protein_bound = 96%

| metabolism =

| metabolism = not identified

| elimination_half-life =

| excretion =

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

| IUPHAR_ligand = 4742

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

| CAS_number = 55837-27-9

| ATC_prefix = C03

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| ATC_supplemental =

| PubChem = 4849

| DrugBank_Ref = {{drugbankcite|~~correct~~|drugbank}}

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

| 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

| molecular_weight = 362.40 g/mol

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

| smiles = C1CCN(C1)C2=C(C(=CC(=C2)C(=O)O)S(=O)(=O)N)OC3=CC=CC=C3

| 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]]<ref>{{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 }}</ref> 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<ref name="AustriaCodex">{{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}}</ref> medication in Germany, France, Italy and other countries.

'''Piretanide''' ([4-phenoxy-3-(1-pyrrolidinyl)-5-sulfamoyl-benzoic acid][[International Nonproprietary Name|INN]])

Piretanide has been synthesized in 1973 at Hoechst AG (Germany) as a diuretic and

saluretic compound by using a new method for introducing cyclic amine residues in an

aromatic nucleus in the presence of other aromatically bonded functional groups like sulfamoyl-,

ester-,nitro-,amino-,hydroxy-,cyano-,halogen- or sulfonylimino-groups.

Intensive studies of piretanide in rats and dogs in comparison with other high-ceiling diuretics

e.g.furosemide and bumetanide revealed its diuretic and saluretic potency with a more

suitable dose/response (regression lines) and a more favourable Na/K excretion ratio.

These findings led eventually to clinical studies in man and finally to the introduction

as a saluretic and antihypertensive<ref>[ Diuretics lecture, pharmacology and therapeutics by Dr. Chris John - Imperial College London]</ref> medication in Germany,France,Italy and other countries.

⚫

~~Trade~~ names: ~~ARELIX~~,Eurelix,Tauliz.

Bibliography :

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)

It was made in 1973, patented in 1974, and approved for medical use in 1981.<ref>{{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}}</ref>

==~~References~~==

==Brand names==

⚫

Brand names include Arelix, Eurelix, Tauliz.

== References ==

== Further reading ==

* {{cite journal | vauthors = Merkel W, Bormann D, Mania D, Muschaweck R, Hropot M | title = Piretanide (HOE118): A new high-ceiling sali-diuretic | journal = European Journal of Medicinal Chemistry | volume = 11 | pages = 399 | year = 1976 }}

* {{cite journal | vauthors = Merkel W, Mania D, Bormann D | title = Selektive Reduktion von Imiden mit funktionellen Gruppen | trans-title = Selective reduction of imides in the presence of other function groups | language = German | journal = Liebigs Annalen der Chemie | volume = 1979 | issue = 4 | pages = 461–9 | year = 1979 | doi = 10.1002/jlac.197919790406 }}

[[Category:Diuretics]]

[[Category:~~Pyrrolidines~~]]

[[Category:1-Pyrrolidinyl compounds]]

[[Category:Phenol ethers]]

[[Category:Benzoic acids]]

[[Category:Carbonic anhydrase inhibitors]]

[[Category:NMDA receptor antagonists]]

[[it:Piretanide]]