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=C(C=CC=C2)N1NC(=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

Molecular Formula C16H16ClN3O3S
Molecular Weight 365.835
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/dosage/indapamide.html

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

Curator's Comment: Indapamide was synthesised by Servier Laboratories in 1969

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Indapamide

Approved Use

Indapamide tablets are indicated for the treatment of hypertension, alone or in combination with other antihypertensive drugs. Indapamide tablets are also indicated for the treatment of salt and fluid retention associated with congestive heart failure.

Launch Date

1998
Primary
Indapamide

Approved Use

Indapamide tablets are indicated for the treatment of hypertension, alone or in combination with other antihypertensive drugs. Indapamide tablets are also indicated for the treatment of salt and fluid retention associated with congestive heart failure.

Launch Date

1998
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
260 ng/mL
5 g single, oral
dose: 5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
INDAPAMIDE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
47.79 ng/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDAPAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
919.52 ng × h/mL
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDAPAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
14 h
5 g single, oral
dose: 5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
INDAPAMIDE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
23.23 h
5 mg single, oral
dose: 5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDAPAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
25%
5 g single, oral
dose: 5 g
route of administration: Oral
experiment type: SINGLE
co-administered:
INDAPAMIDE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2.5 mg 1 times / day multiple, oral
Recommended
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources: Page: p.261
unhealthy, 21 - 73
n = 311
Health Status: unhealthy
Condition: Hypertension
Age Group: 21 - 73
Sex: M+F
Population Size: 311
Sources: Page: p.261
Disc. AE: Hypokalemia...
AEs leading to
discontinuation/dose reduction:
Hypokalemia (0.64%)
Sources: Page: p.261
AEs

AEs

AESignificanceDosePopulation
Hypokalemia 0.64%
Disc. AE
2.5 mg 1 times / day multiple, oral
Recommended
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources: Page: p.261
unhealthy, 21 - 73
n = 311
Health Status: unhealthy
Condition: Hypertension
Age Group: 21 - 73
Sex: M+F
Population Size: 311
Sources: Page: p.261
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Perindopril/indapamide 2/0.625 mg/day: a review of its place in the management of hypertension.
2001
Indapamide plus perindopril--simpler treatment, better compliance.
2001 Apr-May
Comparison of spectrophotometric and an LC method for the determination perindopril and indapamide in pharmaceutical formulations.
2001 Aug
Recommendations for the use of low-dose diuretics.
2001 Aug-Sep
Academic support for combination therapy in hypertension.
2001 Aug-Sep
Progress in reducing the burden of stroke.
2001 Dec
The lowering of blood pressure after stroke.
2001 Dec 8
The lowering of blood pressure after stroke.
2001 Dec 8
The lowering of blood pressure after stroke.
2001 Dec 8
The lowering of blood pressure after stroke.
2001 Dec 8
Significant hypertrophy regression with indapamide sustained release 1.5 mg.
2001 Feb-Mar
[PROGRESS Study examines transient cerebral ischemia and stroke patients. Future goal: attaining basic blood pressure control].
2001 Jul 5
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
Clinical benefit of very-low-dose perindopril-indapamide combination in hypertension.
2001 Nov
Amelioration of arterial properties with a perindopril-indapamide very-low-dose combination.
2001 Nov
[Clinical study of the month. Secondary prevention of cerebrovascular accident with perindopril: the PROGRESS study].
2001 Nov
Sodium intake, large artery stiffness, and proteoglycans in the spontaneously hypertensive rat.
2001 Nov
A double-blind trial of perindopril and nitrendipine in incipient diabetic nephropathy.
2001 Oct
Indapamide-induced pemphigus foliaceus.
2001 Sep
Blood pressure and stroke; the PROGRESS trial.
2001 Sep
[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
Effects of antihypertensive therapy on hemorheological profiles in female hypertensive patients with initially low or high whole blood viscosity.
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 of 12-week monotherapy with arifon-retard of patients with isolated systolic hypertension].
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
[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
Molecular and functional characterization of ERG, KCNQ, and KCNE subtypes in rat stomach smooth muscle.
2002 Feb
The PROGRESS Trial: preventing strokes by lowering blood pressure in patients with cerebral ischemia. Emerging therapies: critique of an important advance.
2002 Jan
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
Hyponatraemia and hypokalaemia caused by indapamide.
2002 Jul 1
Hyponatraemia and hypokalaemia due to indapamide.
2002 Mar 4
Combined therapy with indapamide and perindopril but not perindopril alone reduced the risk for recurrent stroke.
2002 Mar-Apr
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
[The challenge to treat hypertensive patients with type 2 diabetes].
2002 Oct
[Arterial hypertension in elderly individuals].
2002 Oct
[Management of hypertensive patients with left ventricular hypertrophy].
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
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
Drug-drug interactions among elderly patients hospitalized for drug toxicity.
2003 Apr 2
Regression of left ventricular hypertrophy with echocardiography: some lessons from the LIVE study.
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
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

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
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:05:45 GMT 2023
Edited
by admin
on Fri Dec 15 17:05:45 GMT 2023
Record UNII
F089I0511L
Record Status Validated (UNII)
Record Version
  • Download
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 [JAN]
Common Name English
NORANAT
Brand Name English
INDAPAMIDE [MI]
Common Name English
SE-1520
Code English
NSC-757075
Code English
Indapamide [WHO-DD]
Common Name English
indapamide [INN]
Common 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
INDAPAMIDE [EP IMPURITY]
Common Name English
ARIFON
Brand Name English
INDAFLEX
Brand Name English
NATRIX
Brand Name English
INDAPAMIDE [USP MONOGRAPH]
Common Name English
FLUPAMID
Brand Name English
DAMIDE
Brand Name English
LOZOL
Brand Name English
INDAPAMIDE [MART.]
Common Name English
INDAPAMIDE [EP MONOGRAPH]
Common Name English
LORVAS
Brand Name English
FLUDIN
Brand Name English
INDAMIDE
Brand Name English
INDAPAMIDE [USP-RS]
Common Name English
BR-1015 component Indapamide
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 Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
NDF-RT N0000175420
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
WHO-VATC QC03BA11
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
WHO-ATC C03BA11
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
NDF-RT N0000175359
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
LIVERTOX 503
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
WHO-ATC C09BX01
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
WHO-ATC C10BX13
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
WHO-VATC QC09BX01
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
Code System Code Type Description
DRUG CENTRAL
1433
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
ECHA (EC/EINECS)
248-012-7
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
WIKIPEDIA
INDAPAMIDE
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
MERCK INDEX
m6245
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY Merck Index
MESH
D007190
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
IUPHAR
7203
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PRIMARY
PUBCHEM
3702
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
FDA UNII
F089I0511L
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID7044633
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
DAILYMED
F089I0511L
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
LACTMED
Indapamide
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
ChEMBL
CHEMBL406
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
RS_ITEM_NUM
1338801
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PRIMARY
NSC
757075
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PRIMARY
CHEBI
5893
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PRIMARY
EVMPD
SUB08169MIG
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
NCI_THESAURUS
C29119
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
CAS
26807-65-8
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
INN
3333
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
RXCUI
5764
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY RxNorm
SMS_ID
100000092651
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
DRUG BANK
DB00808
Created by admin on Fri Dec 15 17:05:45 GMT 2023 , Edited by admin on Fri Dec 15 17:05:45 GMT 2023
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
EXCRETED UNCHANGED
Lozol is an extensively metabolized drug, with only about 7% of the total dose administered, recovered in the urine as unchanged drug during the first 48 hours after administration.
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
SALT/SOLVATE -> PARENT
BINDER->LIGAND
From 71 to 79% of the Lozol in plasma is reversibly bound to plasma proteins.
REVERSIBLE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
SOLVATE->ANHYDROUS
TARGET -> INHIBITOR
indapamide has both diuretic and vasodilator properties. A low urinary excretion and specific accumulation into arterial smooth muscle of this lipophilic molecule may provide a rationale for this dual activity.
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC