PIRETANIDE

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 Search

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

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.medicines.ie/medicine/2178/SPC/Arelix+Tablets+6mg/

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
Cystic fibrosis transmembrane conductance regulator 6 Target ID: CHEMBL4051 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24117047	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Oedema 7 Sources: http://www.medicines.ie/medicine/2178/SPC/Arelix+Tablets+6mg/	Primary		Approved 8429	Arelix Approved Use Arelix is a diuretic for the management of fluid retention and treatment of mild to moderate hypertension.
Hypertension 567 Sources: http://www.medicines.ie/medicine/2178/SPC/Arelix+Tablets+6mg/	Primary		Approved 8429	Arelix Approved Use Arelix 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	6373442
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	4088324
Differential regulation of collecting duct Na+, K+-ATPase and K+ excretion by furosemide and piretanide: role of bradykinin.	2004 Apr	15034089
A pentylenetetrazole-induced generalized seizure in early life enhances the efficacy of muscarinic receptor coupling to G-protein in hippocampus and neocortex of adult rat.	2005 Apr	15869478
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	16044110
Functional characterization of human monocarboxylate transporter 6 (SLC16A5).	2005 Dec	16174808
Peripheral and central antinociceptive action of Na+-K+-2Cl- cotransporter blockers on formalin-induced nociception in rats.	2005 Mar	15733649
Stability-indicating methods for the determination of piretanide in presence of the alkaline induced degradates.	2005 Oct 4	16223647
[Diuretic therapy in heart failure].	2006 Jan-Feb	16634001
Combined effect of solvent content, temperature and pH on the chromatographic behaviour of ionisable compounds.	2007 Sep 7	17585924
Blood pressure lowering efficacy of loop diuretics for primary hypertension.	2009 Oct 7	19821314
In-vitro characterization of gastroretentive microballoons prepared by the emulsion solvent diffusion method.	2010 Jan	22247832

Patents

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 Created by `admin` on `Sat Dec 16 17:29:52 GMT 2023` Edited by `admin` on `Sat Dec 16 17:29:52 GMT 2023`
Record UNII	DQ6KK6GV93
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PIRETANIDE

Official Name

English

PIRETANIDE [MART.]

Common Name

English

ARELIX

Brand Name

English

HOE 118

Code

English

BENZOIC ACID, 3-(AMINOSULFONYL)-4-PHENOXY-5-(1-PYRROLIDINYL)-

Common Name

English

PIRETANIDE [MI]

Common Name

English

S-73-4118

Code

English

PIRETANIDE [EP MONOGRAPH]

Common Name

English

4-PHENOXY-3-(PYRROLIDINYL)-5-SULFAMOYLBENZOIC ACID

Systematic Name

English

PIRETANIDE [USAN]

Common Name

English

PIRETANIDE [JAN]

Common Name

English

S-734118

Code

English

piretanide [INN]

Common Name

English

HOE-118

Code

English

Piretanide [WHO-DD]

Common Name

English

S 73 4118

Code

English

Classification Tree Code System Code

WHO-VATC

QC03CA03