Piretanide

Piretanide
Clinical data
Trade names	Arelix, Eurelix, Tauliz
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	C03CA03 (WHO) ;
Legal status
Legal status	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 g·mol−1
3D model (JSmol)	Interactive image;
	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

^ 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. {{cite book}}: |first1= has generic name (help)CS1 maint: multiple names: authors list (link)
^ 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.
^ 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).

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[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. {{cite book}}: |first1= has generic name (help)CS1 maint: multiple names: authors list (link)

[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.

[AustriaCodex-3] Haberfeld, H, ed. (2009). Austria-Codex (in German) (2009/2010 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 3-85200-196-X.

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