Piretanide

Piretanide

Systematic (IUPAC) name
3-(aminosulfonyl)-4-phenoxy-5-pyrrolidin-1-ylbenzoic acid
Clinical data
Trade names	Arelix, Eurelix, Tauliz
AHFS/Drugs.com	International Drug Names
Legal status	℞ (Prescription only)
Routes of administration	Oral
Pharmacokinetic data
Bioavailability	~90%
Protein binding	96%
Metabolism	not identified
Excretion	Urine (60%), feces (40%)
Identifiers
CAS Number	55837-27-9 Y
ATC code	C03CA03 (WHO)
PubChem	CID: 4849
IUPHAR/BPS	4742
DrugBank	DB02925 N
ChemSpider	4683 N
UNII	DQ6KK6GV93 Y
KEGG	D01634 Y
Chemical data
Formula	C17H18N2O5S
Molecular mass	362.40 g/mol
SMILES C1CCN(C1)C2=C(C(=CC(=C2)C(=O)O)S(=O)(=O)N)OC3=CC=CC=C3
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)

Piretanide (INN, trade names Arelix, Eurelix, Tauliz) has been synthesized in 1973 at Hoechst AG (Germany) as a loop diuretic 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 clinical studies in man and finally to the introduction as a saluretic and antihypertensive medication in Germany, France, Italy and other countries.

References

• 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).