U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C16H16ClN3O3S
Molecular Weight 365.835
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDAPAMIDE

SMILES

CC1CC2=CC=CC=C2N1NC(=O)C3=CC(=C(Cl)C=C3)S(N)(=O)=O

InChI

InChIKey=NDDAHWYSQHTHNT-UHFFFAOYSA-N
InChI=1S/C16H16ClN3O3S/c1-10-8-11-4-2-3-5-14(11)20(10)19-16(21)12-6-7-13(17)15(9-12)24(18,22)23/h2-7,9-10H,8H2,1H3,(H,19,21)(H2,18,22,23)

HIDE SMILES / InChI

Description

Indapamide is an antihypertensive and a diuretic. It contains both a polar sulfamoyl chlorobenzamide moiety and a lipid- soluble methylindoline moiety. Indapamide blocks the slow component of delayed rectifier potassium current (IKs) without altering the rapid component (IKr) or the inward rectifier current. Specifically it blocks or antagonizes the action the proteins KCNQ1 and KCNE1. Indapamide is also thought to stimulate the synthesis of the vasodilatory hypotensive prostaglandin PGE2. Indapamide is used for the treatment of hypertension, alone or in combination with other antihypertensive drugs, as well as for the treatment of salt and fluid retention associated with congestive heart failure or edema from pregnancy (appropriate only in the management of edema of pathologic origin during pregnancy when clearly needed). Also used for the management of edema as a result of various causes.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Antihypertensive action of indapamide. Comparative studies in several experimental models.
1975 Oct
Progress in reducing the burden of stroke.
2001 Dec
Effects of combination of low doses of angiotensin-converting enzyme inhibitor and diuretics on renal function in spontaneously hypertensive rats: comparison between acute and chronic treatment.
2001 Jun
[CEA comprehensive evaluation for Western and traditional Chinese hypotensive drugs].
2001 Sep
Indapamide-induced pemphigus foliaceus.
2001 Sep
Blood pressure and stroke; the PROGRESS trial.
2001 Sep
[Changes of distensibility of the aorta in elderly patients during long-term therapy with various classes of hypotensive drugs (magnetic resonance tomography data)].
2002
[Tolerability and efficacy of retard form of indapamide in the treatment of hypertension in elderly patients (results of multicenter open non-comparative trial in Russian program ARGUS)].
2002
[Clinical assessment of efficacy and safety of noliprel in patients with hypertension].
2002
The effects of the addition of micronised fenofibrate on uric acid metabolism in patients receiving indapamide.
2002
Cutaneous drug reaction case reports: from the world literature.
2002
[Efficacy and tolerance of rilmenidine in patients with mild to moderate hypertension. Results of a Czech and Slovak 6-month multicenter study].
2002 Aug
[Arterial hypertension and tachycardia: monitoring the patient's personal drug therapy].
2002 Aug
Gender influence on the dose-ranging of a low-dose perindopril-indapamide combination in hypertension: effect on systolic and pulse pressure.
2002 Aug
[Indapamide-induced pemphigus foliaceus a sulfurous affair?].
2002 Aug-Sep
Effects of four antihypertensive monotherapies on cardiac mass and function in hypertensive patients with left ventricular hypertrophy: randomized prospective study.
2002 Dec
Hypokalaemia and hyponatraemia due to indapamide.
2002 Dec
Very-low-dose combination of the angiotensin-converting enzyme inhibitor perindopril and the diuretic indapamide induces an early and sustained increase in neovascularization in rat ischemic legs.
2002 Dec
Efficacious response with low-dose indapamide therapy in the treatment of type II diabetic patients with normal renal function or moderate renal insufficiency and moderate hypertension.
2002 Jan-Feb
Comparison of indapamide and low-dose hydrochlorothiazide monotherapy in black patients with mild to moderate hypertension.
2002 Jul
[Pigmented lesions secondary to indapamide].
2002 Jul
Hyponatraemia and hypokalaemia caused by indapamide.
2002 Jul 1
Hyponatraemia and hypokalaemia due to indapamide.
2002 Mar 4
Stroke prevention: management of modifiable vascular risk factors.
2002 May
[PROGRESS--a trial on blood pressure lowering after stroke and TIA. ACE inhibitors and diuretics reduce the risk of new stroke].
2002 May 16
Fixed combinations of delapril plus indapamide vs fosinopril plus hydrochlorothiazide in mild to moderate essential hypertension.
2002 May-Jun
[Reflexion of French experts on the key points of the symposium].
2002 Oct
[Treatment of hypertensive type 2 diabetes patients with microalbuminuria].
2002 Oct
Water vapor absorption into amorphous hydrophobic drug/poly(vinylpyrrolidone) dispersions.
2002 Oct
Drug-induced long QT in isolated rabbit Purkinje fibers: importance of action potential duration, triangulation and early afterdepolarizations.
2002 Oct 4
[Hypertension and microcirculation].
2002 Sep
[Combination of low-dose perindopril/indapamide versus atenolol in the hypertensive patient. Effects on systolic pressure and arterial hemodynamics. REASON Study].
2002 Sep
Indapamide induced syncope in a patient with long QT syndrome.
2002 Sep
Efficacy of very low dose perindopril 2 mg/indapamide 0.625 mg combination on left ventricular hypertrophy in hypertensive patients: the P.I.C.X.E.L. study rationale and design.
2002 Sep
Two derivative spectrophotometric determinations of indapamide in pharmaceutical dosage forms.
2002 Sep 5
[Coversyl again].
2002 Sep 9
Progress and stroke--it's time to translate evidence into action.
2002 Sep-Oct
The Perindopril Protection Against Recurrent Stroke Study (PROGRESS): clinical implications for older patients with cerebrovascular disease.
2003
Drug-drug interactions among elderly patients hospitalized for drug toxicity.
2003 Apr 2
Evaluation of the efficacy and tolerability of the combination delapril plus indapamide in the treatment of mild to moderate essential hypertension: a randomised, multicentre, controlled study.
2003 Feb
Prevention of stone formation and bone loss in absorptive hypercalciuria by combined dietary and pharmacological interventions.
2003 Feb
Regression of left ventricular hypertrophy with echocardiography: some lessons from the LIVE study.
2003 Jan
Converting enzyme inhibitor or AT1-receptor blocker for decreasing long-term mortality in patients with stroke history and renal dysfunction?
2003 Jan
Blinded test in isolated female rabbit heart reliably identifies action potential duration prolongation and proarrhythmic drugs: importance of triangulation, reverse use dependence, and instability.
2003 Jan
[Secondary prevention after ischemic stroke].
2003 Jan 29
Cardiovascular protective role of a low-dose antihypertensive combination in obese Zucker rats.
2003 Mar
Effects of a perindopril-based blood pressure lowering regimen on cardiac outcomes among patients with cerebrovascular disease.
2003 Mar
Mechanisms of adrenergic control of sino-atrial node discharge.
2003 Mar-Apr
Effect of low-dose perindopril/indapamide on albuminuria in diabetes: preterax in albuminuria regression: PREMIER.
2003 May
Optimization of a solid-phase extraction method for determination of indapamide in biological fluids using high-performance liquid chromatography.
2003 May 5
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Edema Initial dose: 2.5 mg orally once a day. Usual Adult Dose for Hypertension Initial dose: 1.25 mg orally once a day.
Route of Administration: Oral
In Vitro Use Guide
10(-4) M Indapamide decreased bone resorption in organ cultures and in cocultures of osteoblast-like cells and bone marrow cells in the presence of 10(-8) M 1,25-dihydroxyvitamin D3
Name Type Language
INDAPAMIDE
EP   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
IPAMIX
Brand Name English
INDAPAMIDE [USAN]
Common Name English
INDAPAMIDE [USP]
Common Name English
INDAPAMIDE [JAN]
Common Name English
NORANAT
Brand Name English
INDAPAMIDE [MI]
Common Name English
SE-1520
Code English
INDAPAMIDE [INN]
Common Name English
BENZAMIDE, 3-(AMINOSULFONYL)-4-CHLORO-N-(2,3-DIHYDRO-2-METHYL-1H-INDOL-1-YL)-
Systematic Name English
BAJATEN
Brand Name English
NATRILIX
Brand Name English
KYD-041
Code English
INDAPAMIDE [VANDF]
Common Name English
TANDIX
Common Name English
FLUDEX
Brand Name English
INDAMOL
Brand Name English
FLUBEST
Brand Name English
4-CHLORO-N-(2-METHYL-1-INDOLINYL)-3-SULFAMOYLBENZAMIDE
Systematic Name English
TERTENSIF
Brand Name English
ARIFON
Brand Name English
INDAFLEX
Brand Name English
NATRIX
Brand Name English
FLUPAMID
Brand Name English
DAMIDE
Brand Name English
LOZOL
Brand Name English
INDAPAMIDE [MART.]
Common Name English
LORVAS
Brand Name English
FLUDIN
Brand Name English
INDAMIDE
Brand Name English
INDAPAMIDE [USP-RS]
Common Name English
INDAPAMIDE [EP]
Common Name English
INDAPAMIDE [WHO-DD]
Common Name English
INDAPAMIDE [ORANGE BOOK]
Common Name English
S-1520
Code English
VEROXIL
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C49185
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
NDF-RT N0000175420
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
WHO-VATC QC03BA11
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
WHO-ATC C03BA11
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
NDF-RT N0000175359
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
LIVERTOX 503
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
WHO-ATC C09BX01
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
WHO-ATC C10BX13
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
WHO-VATC QC09BX01
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
Code System Code Type Description
ECHA (EC/EINECS)
248-012-7
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
PRIMARY
LactMed
26807-65-8
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
PRIMARY
WIKIPEDIA
INDAPAMIDE
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
PRIMARY
MERCK INDEX
M6245
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
PRIMARY Merck Index
MESH
D007190
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
PRIMARY
IUPHAR
7203
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
PRIMARY
PUBCHEM
3702
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
PRIMARY
EPA CompTox
26807-65-8
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
PRIMARY
ChEMBL
CHEMBL406
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
PRIMARY
EVMPD
SUB08169MIG
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
PRIMARY
NCI_THESAURUS
C29119
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
PRIMARY
CAS
26807-65-8
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
PRIMARY
INN
3333
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
PRIMARY
RXCUI
5764
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
PRIMARY RxNorm
DRUG BANK
DB00808
Created by admin on Tue Oct 22 00:33:48 UTC 2019 , Edited by admin on Tue Oct 22 00:33:48 UTC 2019
PRIMARY