INDAPAMIDE

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 Search

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

Targets

Primary Target	Pharmacology	Condition	Potency
Carbonic anhydrase XII 18	Inhibitor 6523	Heart Failure	10.0 nM [Ki]
Voltage-gated potassium channel subunit Kv7.1 3	Inhibitor 6523	Heart Failure
Voltage-gated potassium channel beta subunit Mink 2	Inhibitor 6523	Heart Failure
Carbonic anhydrase IX 31	Inhibitor 6523	Heart Failure	36.0 nM [Ki]
Carbonic anhydrase VII 24	Inhibitor 6523	Heart Failure	0.23 nM [Ki]
Thiazide-sensitive sodium-chloride cotransporter 19	Inhibitor 6523	Heart Failure

Conditions

Condition	Modality	Targets	Highest Phase	Product
Heart Failure 136	Primary	Voltage-gated potassium channel subunit Kv7.1 Voltage-gated potassium channel beta subunit Mink Thiazide-sensitive sodium-chloride cotransporter Carbonic anhydrase IX Carbonic anhydrase XII Carbonic anhydrase VII	Approved 7109	Indapamide
Hypertension 481	Primary	Voltage-gated potassium channel subunit Kv7.1 Voltage-gated potassium channel beta subunit Mink Thiazide-sensitive sodium-chloride cotransporter Carbonic anhydrase IX Carbonic anhydrase XII Carbonic anhydrase VII	Approved 7109	Indapamide
Calcium nephrolithiasis 2			Approved (off-label) 8

PubMed

Title	Date	PubMed
Antihypertensive action of indapamide. Comparative studies in several experimental models.	1975 Oct	1243026
Progress in reducing the burden of stroke.	2001 Dec	11903323
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	11881108
[CEA comprehensive evaluation for Western and traditional Chinese hypotensive drugs].	2001 Sep	12575552
Indapamide-induced pemphigus foliaceus.	2001 Sep	12243711
Blood pressure and stroke; the PROGRESS trial.	2001 Sep	11881116
[Changes of distensibility of the aorta in elderly patients during long-term therapy with various classes of hypotensive drugs (magnetic resonance tomography data)].	2002	12494142
[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	12494109
[Clinical assessment of efficacy and safety of noliprel in patients with hypertension].	2002	12494074
The effects of the addition of micronised fenofibrate on uric acid metabolism in patients receiving indapamide.	2002	12017210
Cutaneous drug reaction case reports: from the world literature.	2002	11978142
[Efficacy and tolerance of rilmenidine in patients with mild to moderate hypertension. Results of a Czech and Slovak 6-month multicenter study].	2002 Aug	12425202
[Arterial hypertension and tachycardia: monitoring the patient's personal drug therapy].	2002 Aug	12405021
Gender influence on the dose-ranging of a low-dose perindopril-indapamide combination in hypertension: effect on systolic and pulse pressure.	2002 Aug	12172328
[Indapamide-induced pemphigus foliaceus a sulfurous affair?].	2002 Aug-Sep	12442120
Effects of four antihypertensive monotherapies on cardiac mass and function in hypertensive patients with left ventricular hypertrophy: randomized prospective study.	2002 Dec	12476475
Hypokalaemia and hyponatraemia due to indapamide.	2002 Dec	12472097
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	12438525
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	11919395
Comparison of indapamide and low-dose hydrochlorothiazide monotherapy in black patients with mild to moderate hypertension.	2002 Jul	12197195
[Pigmented lesions secondary to indapamide].	2002 Jul	12162228
Hyponatraemia and hypokalaemia caused by indapamide.	2002 Jul 1	12088485
Hyponatraemia and hypokalaemia due to indapamide.	2002 Mar 4	11999238
Stroke prevention: management of modifiable vascular risk factors.	2002 May	12021938
[PROGRESS--a trial on blood pressure lowering after stroke and TIA. ACE inhibitors and diuretics reduce the risk of new stroke].	2002 May 16	12082946
Fixed combinations of delapril plus indapamide vs fosinopril plus hydrochlorothiazide in mild to moderate essential hypertension.	2002 May-Jun	12201354
[Reflexion of French experts on the key points of the symposium].	2002 Oct	12356003
[Treatment of hypertensive type 2 diabetes patients with microalbuminuria].	2002 Oct	12356001
Water vapor absorption into amorphous hydrophobic drug/poly(vinylpyrrolidone) dispersions.	2002 Oct	12226842
Drug-induced long QT in isolated rabbit Purkinje fibers: importance of action potential duration, triangulation and early afterdepolarizations.	2002 Oct 4	12354568
[Hypertension and microcirculation].	2002 Sep	12407782
[Combination of low-dose perindopril/indapamide versus atenolol in the hypertensive patient. Effects on systolic pressure and arterial hemodynamics. REASON Study].	2002 Sep	12407781
Indapamide induced syncope in a patient with long QT syndrome.	2002 Sep	12380780
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	12214263
Two derivative spectrophotometric determinations of indapamide in pharmaceutical dosage forms.	2002 Sep 5	12191722
[Coversyl again].	2002 Sep 9	12362877
Progress and stroke--it's time to translate evidence into action.	2002 Sep-Oct	12557875
The Perindopril Protection Against Recurrent Stroke Study (PROGRESS): clinical implications for older patients with cerebrovascular disease.	2003	12641480
Drug-drug interactions among elderly patients hospitalized for drug toxicity.	2003 Apr 2	12672733
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	12574793
Prevention of stone formation and bone loss in absorptive hypercalciuria by combined dietary and pharmacological interventions.	2003 Feb	12544288
Regression of left ventricular hypertrophy with echocardiography: some lessons from the LIVE study.	2003 Jan	12544454
Converting enzyme inhibitor or AT1-receptor blocker for decreasing long-term mortality in patients with stroke history and renal dysfunction?	2003 Jan	12511742
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	12500017
[Secondary prevention after ischemic stroke].	2003 Jan 29	12643070
Cardiovascular protective role of a low-dose antihypertensive combination in obese Zucker rats.	2003 Mar	12640256
Effects of a perindopril-based blood pressure lowering regimen on cardiac outcomes among patients with cerebrovascular disease.	2003 Mar	12633548
Mechanisms of adrenergic control of sino-atrial node discharge.	2003 Mar-Apr	12595754
Effect of low-dose perindopril/indapamide on albuminuria in diabetes: preterax in albuminuria regression: PREMIER.	2003 May	12654706
Optimization of a solid-phase extraction method for determination of indapamide in biological fluids using high-performance liquid chromatography.	2003 May 5	12668086

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

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