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
Routes of administration	Oral
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	~90%[1]
Protein binding	96%
Metabolism	not identified
Excretion	Urine (60%), feces (40%)
Identifiers
CAS Number	55837-27-9
ATC code	C03CA03 (WHO)
PubChem	CID 4849
IUPHAR/BPS	4742
DrugBank	DB02925
ChemSpider	4683
UNII	DQ6KK6GV93
KEGG	D01634
Chemical data
Formula	C17H18N2O5S
Molar 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) Key:UJEWTUDSLQGTOA-UHFFFAOYSA-N
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Piretanide (INN, trade names Arelix, Eurelix, Tauliz) has been synthesized in 1973 at Hoechst AG (Germany) as a loop diuretic^[2] 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^[3] medication in Germany, France, Italy and other countries.

References

1. Mutschler, Edited by Rainer F. Greger, H. Knauf, E. Mutschler (1995). Diuretics. Handbook of Experimental Pharmacology (Том 117). Berlin, Heidelberg: Springer Science & Business Media, 2012. p. 517. ISBN 364279565X.
2. Musini, V. M.; Wright, J. M.; Bassett, K.; Jauca, C. D. (2009). Musini, Vijaya M, ed. "Blood pressure lowering efficacy of loop diuretics for primary hypertension". The Cochrane Library (4): CD003825. doi:10.1002/14651858.CD003825.pub2. PMID 19821314.
3. Haberfeld, H, ed. (2009). Austria-Codex (in German) (2009/2010 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 3-85200-196-X.

• 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).