Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C17H17N2O5S.Na |
| Molecular Weight | 384.382 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].NS(=O)(=O)C1=C(OC2=CC=CC=C2)C(=CC(=C1)C([O-])=O)N3CCCC3
InChI
InChIKey=HZVLWIUJVNFUMW-UHFFFAOYSA-M
InChI=1S/C17H18N2O5S.Na/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);/q;+1/p-1
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 medication in Germany, France, Italy and other countries.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL4051 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Arelix Approved UseArelix is a diuretic for the management of fluid retention and treatment of mild to moderate hypertension. |
|||
| Primary | Arelix Approved UseArelix is a diuretic for the management of fluid retention and treatment of mild to moderate hypertension. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| A double-blind multicentre study of piretanide and hydrochlorothiazide in patients with essential hypertension. | 1984 |
|
| Quantitative evaluation of ototoxic side effects of furosemide, piretanide, bumetanide, azosemide and ozolinone in the cat--a new approach to the problem of ototoxicity. | 1985 Nov |
|
| Screening procedure for detection of diuretics and uricosurics and/or their metabolites in human urine using gas chromatography-mass spectrometry after extractive methylation. | 2005 Aug |
|
| Stability-indicating methods for the determination of piretanide in presence of the alkaline induced degradates. | 2005 Oct 4 |
|
| [Diuretic therapy in heart failure]. | 2006 Jan-Feb |
Sample Use Guides
Oedema: The usual initial adult dose is 6mg daily, adjusted according to response to a maximum of 30mg. An initial dose of 3mg may be sufficient in some patients.
Hypertension: The usual initial adult dose is 6mg daily in mild to moderate hypertension. This dose should be continued for 2-4 weeks then increased if necessary at 2-4 week intervals to a maximum of 18mg daily. The maintenance dose is usually 6mg daily.
Route of Administration:
Oral
To investigate the voltage and external Cl− concentration dependence of channel block, we used voltage-ramp protocols to acquire current–voltage (I–V) relationships To explore the time dependence of blockade, we bathed membrane patches in symmetrical Cl−-rich solutions and stepped voltage first from 0 to −100 mV and then from −100 to +100 mV before returning to 0 mV; the duration of each voltage step was 250 ms. We averaged multiple current records (5–30) acquired in the absence and presence of drugs before subtracting basal currents with no active channels recorded in the absence of PKA (75 nM) and ATP (1 mM) to isolate macroscopic CFTR Cl− currents.
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ACTIVE MOIETY
SUBSTANCE RECORD
