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=CC(=CC(N2CCCC2)=C1OC3=CC=CC=C3)C(O)=O

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 7 Target ID: CHEMBL4051 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24117047	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Oedema 7 Sources: http://www.medicines.ie/medicine/2178/SPC/Arelix+Tablets+6mg/	Primary		Approved 8583	Arelix Approved Use Arelix is a diuretic for the management of fluid retention and treatment of mild to moderate hypertension.
Hypertension 575 Sources: http://www.medicines.ie/medicine/2178/SPC/Arelix+Tablets+6mg/	Primary		Approved 8583	Arelix Approved Use Arelix is a diuretic for the management of fluid retention and treatment of mild to moderate hypertension.

C_max

Value	Dose	Co-administered	Analyte	Population
366 mg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3449067/	6 mg single, intramuscular dose: 6 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		PIRETANIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
2.05 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6342640/	18 mg 2 times / day multiple, oral dose: 18 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PIRETANIDE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.08 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6519164/	24 mg single, oral dose: 24 mg route of administration: Oral experiment type: SINGLE co-administered:	PIRETANIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
4.68 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6519164/	48 mg single, oral dose: 48 mg route of administration: Oral experiment type: SINGLE co-administered:	PIRETANIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8.23 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6519164/	96 mg single, oral dose: 96 mg route of administration: Oral experiment type: SINGLE co-administered:	PIRETANIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
51095 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2506054/	6 mg single, intravenous dose: 6 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PIRETANIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
2.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6342640/	18 mg 2 times / day multiple, oral dose: 18 mg route of administration: Oral experiment type: MULTIPLE co-administered:	PIRETANIDE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.29 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3449067/	6 mg single, intravenous dose: 6 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PIRETANIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
97 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2506054/	6 mg single, intravenous dose: 6 mg route of administration: Intravenous experiment type: SINGLE co-administered:	PIRETANIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
12 mg single, intravenous Studied dose Dose: 12 mg Route: intravenous Route: single Dose: 12 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6840162/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6840162/	Sources: https://pubmed.ncbi.nlm.nih.gov/6840162/
48 mg single, oral Studied dose Dose: 48 mg Route: oral Route: single Dose: 48 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7213511/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7213511/	Sources: https://pubmed.ncbi.nlm.nih.gov/7213511/
6 mg 1 times / day steady-state, oral Studied dose Dose: 6 mg, 1 times / day Route: oral Route: steady-state Dose: 6 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7060317/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7060317/	Sources: https://pubmed.ncbi.nlm.nih.gov/7060317/

PubMed

Title	Date	PubMed
In-vitro characterization of gastroretentive microballoons prepared by the emulsion solvent diffusion method.	2010-01	22247832
Blood pressure lowering efficacy of loop diuretics for primary hypertension.	2009-10-07	19821314
Combined effect of solvent content, temperature and pH on the chromatographic behaviour of ionisable compounds.	2007-09-07	17585924
[Diuretic therapy in heart failure].	2006-04-25	16634001
Functional characterization of human monocarboxylate transporter 6 (SLC16A5).	2005-12	16174808
Stability-indicating methods for the determination of piretanide in presence of the alkaline induced degradates.	2005-10-04	16223647
Screening procedure for detection of diuretics and uricosurics and/or their metabolites in human urine using gas chromatography-mass spectrometry after extractive methylation.	2005-08	16044110
Thiopurine S-methyltransferase as a target for drug interactions.	2005-07	15952020
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.	2005-04	15869478
Peripheral and central antinociceptive action of Na+-K+-2Cl- cotransporter blockers on formalin-induced nociception in rats.	2005-03	15733649
Differential regulation of collecting duct Na+, K+-ATPase and K+ excretion by furosemide and piretanide: role of bradykinin.	2004-04	15034089
Effects of pH and the presence of micelles on the resolution of diuretics by reversed-phase liquid chromatography.	2004-01-02	14753771
Comparison of a preliminary procedure for the general unknown screening of drugs and toxic compounds using a quadrupole-linear ion-trap mass spectrometer with a liquid chromatography-mass spectrometry reference technique.	2003-06-05	12726839
Rat NKCC2/NKCC1 cotransporter selectivity for loop diuretic drugs.	2002-03	11882915
Drug interaction: omeprazole and phenprocoumon.	2001	11313000
Quantitative evaluation of ototoxic side effects of furosemide, piretanide, bumetanide, azosemide and ozolinone in the cat--a new approach to the problem of ototoxicity.	1985-11	4088324
A double-blind multicentre study of piretanide and hydrochlorothiazide in patients with essential hypertension.	1984	6373442

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 `Wed Apr 02 09:13:55 GMT 2025` Edited by `admin` on `Wed Apr 02 09:13:55 GMT 2025`
Record UNII	DQ6KK6GV93
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ARELIX

Preferred Name

English

PIRETANIDE

Official Name

English

PIRETANIDE [MART.]

Common 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