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piretanide
Sign in to savePiretanide is 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 studies in man and finally to the introduction as a saluretic and antihypertensive medication in Germany, France, Italy and other countries.
Chemical data
- Formula
- C17H18N2O5S
- Molecular weight
- 362.4 g/mol
- IUPAC name
- 4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid
- SMILES
- C1CCN(C1)C2=C(C(=CC(=C2)C(=O)O)S(=O)(=O)N)OC3=CC=CC=C3
- InChIKey
- UJEWTUDSLQGTOA-UHFFFAOYSA-N
- XLogP
- 2.2
- Polar surface area
- 118 Ų
- H-bond donors
- 2
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- Indications
- cardiovascular disease
via ChEMBL · EBI
Research
347 papers- Piretanide. A preliminary review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy.Drugs · 1985
- Piretanide: a loop-active diuretic. Pharmacology, therapeutic efficacy and adverse effects.Pharmacotherapy · 1984
- Piretanide for hypertension.Drug and therapeutics bulletin · 1985
- Loop diuretics.Renal physiology · 1987
- The absorption of piretanide from the gastro-intestinal tract is site-dependent.European journal of clinical pharmacology · 1986
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 362.093643
- Has use
- medication
Show 4 more facts
- chemical formula
- C₁₇H₁₈N₂O₅S
- canonical SMILES
- C1CCN(C1)C2=C(C(=CC(=C2)C(=O)O)S(=O)(=O)N)OC3=CC=CC=C3
- subject has role
- diuretic
- Commons category
- Piretanide
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Brand names
- References
- Further reading
Piretanide is 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 studies in man and finally to the introduction as a saluretic and antihypertensive medication in Germany, France, Italy and other countries.
It was made in 1973, patented in 1974, and approved for medical use in 1981.
Excerpted from Wikipedia’s “piretanide” article, available under the CC BY-SA 4.0 licence.
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via Wikidata sitelinks · CC0