Piretanide

Piretanide
Clinical data
Trade names	Arelix, Eurelix, Tauliz, others
AHFS/Drugs.com	International Drug Names
Routes of; administration	By mouth
ATC code	C03CA03 (WHO) ;
Legal status
Legal status	EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	~90%
Protein binding	96%
Metabolism	not identified
Excretion	Urine (60%), feces (40%)
Identifiers
	IUPAC name 3-(aminosulfonyl)-4-phenoxy-5-pyrrolidin-1-ylbenzoic acid;
CAS Number	55837-27-9 ;
PubChem CID	4849;
IUPHAR/BPS	4742;
DrugBank	DB02925 ;
ChemSpider	4683 ;
UNII	DQ6KK6GV93;
KEGG	D01634 ;
CompTox Dashboard (EPA)	DTXSID2023488 ;
ECHA InfoCard	100.054.394
Chemical and physical data
Formula	C17H18N2O5S
Molar mass	362.40 g·mol−1
3D model (JSmol)	Interactive image;
	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) ; Key:UJEWTUDSLQGTOA-UHFFFAOYSA-N ;
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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.