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Details

Stereochemistry ACHIRAL
Molecular Formula C17H18N2O5S
Molecular Weight 362.4
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRETANIDE

SMILES

NS(=O)(=O)C1=C(OC2=CC=CC=C2)C(=CC(=C1)C(O)=O)N3CCCC3

InChI

InChIKey=UJEWTUDSLQGTOA-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C17H18N2O5S
Molecular Weight 362.4
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Arelix
Primary
Arelix

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Substance Class Chemical
Record UNII
DQ6KK6GV93
Record Status Validated (UNII)
Record Version