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 [1] In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	~90% [2]
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  Y
PubChem CID	4849
IUPHAR/BPS	4742
DrugBank	DB02925  N
ChemSpider	4683  N
UNII	DQ6KK6GV93
KEGG	D01634  Y
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) N Key:UJEWTUDSLQGTOA-UHFFFAOYSA-N N
NY  (what is this?)    (verify)

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.

It was made in 1973, patented in 1974, and approved for medical use in 1981. ^[5]

Brand names

Brand names include Arelix, Eurelix, Tauliz.

References

1. "List of nationally authorised medicinal products: Active substance: piretanide: Procedure no.: PSUSA/00002433/202110" (PDF). Ema.europa.eu. Retrieved 28 June 2022.
2. Mutschler E (1995). Greger RF, Knauf H, Mutschler E (eds.). Diuretics. Handbook of Experimental Pharmacology. Vol. 117. Berlin, Heidelberg: Springer Science & Business Media. p. 517. ISBN   978-3-642-79565-7.
3. Musini VM, Rezapour P, Wright JM, Bassett K, Jauca CD (May 2015). "Blood pressure-lowering efficacy of loop diuretics for primary hypertension". The Cochrane Database of Systematic Reviews. 2015 (5) CD003825. doi:10.1002/14651858.CD003825.pub4. PMC   7156893 . PMID   26000442.
4. Haberfeld H, ed. (2009). Austria-Codex (in German) (2009/2010 ed.). Vienna: Österreichischer Apothekerverlag. ISBN   978-3-85200-196-8.
5. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 458. ISBN   978-3-527-60749-5.

Further reading

• Merkel W, Bormann D, Mania D, Muschaweck R, Hropot M (1976). "Piretanide (HOE118): A new high-ceiling sali-diuretic". European Journal of Medicinal Chemistry. 11: 399.
• Merkel W, Mania D, Bormann D (1979). "Selektive Reduktion von Imiden mit funktionellen Gruppen" [Selective reduction of imides in the presence of other function groups]. Liebigs Annalen der Chemie (in German). 1979 (4): 461–9. doi:10.1002/jlac.197919790406.