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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

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

Servier
42
Curator's Comment: Indapamide was synthesised by Servier Laboratories in 1969

Approval Year

1983
53
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8146
Inhibitor
8146
Inhibitor
8146
 36.0 nM [Ki]
Inhibitor
8146
 10.0 nM [Ki]
Inhibitor
8146
 0.23 nM [Ki]
Inhibitor
8146
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8307
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

9.0106561E11
Primary
Approved
8307
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

9.0106561E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
260 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/018538s028lbl.pdf
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/23447043
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/23447043
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/018538s028lbl.pdf
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
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/23447043
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%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/018538s028lbl.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/6346848
Page: p.261
unhealthy, 21 - 73
n = 311
Health Status: unhealthy
Condition: Hypertension
Age Group: 21 - 73
Sex: M+F
Population Size: 311
Sources:
https://pubmed.ncbi.nlm.nih.gov/6346848
Page: p.261
Disc. AE: Hypokalemia...
AEs leading to
discontinuation/dose reduction:
Hypokalemia (0.64%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/6346848
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:
https://pubmed.ncbi.nlm.nih.gov/6346848
Page: p.261
unhealthy, 21 - 73
n = 311
Health Status: unhealthy
Condition: Hypertension
Age Group: 21 - 73
Sex: M+F
Population Size: 311
Sources:
https://pubmed.ncbi.nlm.nih.gov/6346848
Page: p.261
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1670
substrate
985
inhibitor
1570

OverviewOther

Other InhibitorOther SubstrateOther Inducer
OAT3
625

OATP1B3
691
CYP2C19
955

CYP2C8
670
CYP2C23
8

CYP4A1
17
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP4A1
25
 no
OAT3
627
 yes [IC50 11 uM]
OATP1B3
700
 yes [Inhibition 10 uM]
CYP2C23
8
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1670
 major
CYP2C19
955
 yes
CYP2C8
670
 yes
CYP2C9
985
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1603
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:5893
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5893
ChemicalBook
CB2420420
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2420420
MolPort
MolPort-003-666-209
https://www.molport.com/shop/molecule-link/MolPort-003-666-209
Selleck Chemicals
Indapamide(Lozol)
http://www.selleckchem.com/products/Indapamide(Lozol).html
eMolecules
539574
https://www.emolecules.com/cgi-bin/more?vid=539574
PubMed

PubMed

TitleDatePubMed
A comparative study of the activity of a new agent, indapamide, in essential arterial hypertension.
1975
[Effects of perindopril and its combination with indapamide on risk stratification in patients with hypertension].
2001
Perindopril/indapamide 2/0.625 mg/day: a review of its place in the management of hypertension.
2001
Hypertension in the Very Elderly Trial (HYVET): protocol for the main trial.
2001
Pulse wave velocity as endpoint in large-scale intervention trial. The Complior study. Scientific, Quality Control, Coordination and Investigation Committees of the Complior Study.
2001 Apr
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
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
A comparison of indapamide SR 1.5 mg with both amlodipine 5 mg and hydrochlorothiazide 25 mg in elderly hypertensive patients: a randomized double-blind controlled study.
2001 Feb
Indapamide, a thiazide-like diuretic, decreases bone resorption in vitro.
2001 Feb
[New fixed combination for therapy of hypertension. "Softener" and "stimulant" supplement each other].
2001 Feb 1
Celecoxib-induced cholestatic hepatitis.
2001 Feb 6
Coronary microvasculature alteration in hypertensive rats. Effect of treatment with a diuretic and an ACE inhibitor.
2001 Jan
Stripping voltammetric determination of indapamide in serum at castor oil-based carbon paste electrodes.
2001 Jan
Functional consequences of the arrhythmogenic G306R KvLQT1 K+ channel mutant probed by viral gene transfer in cardiomyocytes.
2001 May 15
Clinical benefit of very-low-dose perindopril-indapamide combination in hypertension.
2001 Nov
[Clinical study of the month. Secondary prevention of cerebrovascular accident with perindopril: the PROGRESS study].
2001 Nov
[Efficacy of a converting enzyme inhibitor in the prevention of recurrence of stroke].
2001 Nov 24
[CEA comprehensive evaluation for Western and traditional Chinese hypotensive drugs].
2001 Sep
Very-low-dose combination of perindopril and indapamide as a novel strategy in first-line management of hypertension.
2001 Sep
Growth inhibitory activity of indapamide on vascular smooth muscle cells.
2001 Sep 28
Randomised trial of a perindopril-based blood-pressure-lowering regimen among 6,105 individuals with previous stroke or transient ischaemic attack.
2001 Sep 29
[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
Effects of four antihypertensive monotherapies on cardiac mass and function in hypertensive patients with left ventricular hypertrophy: randomized prospective study.
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
Combined therapy with indapamide and perindopril but not perindopril alone reduced the risk for recurrent stroke.
2002 Mar-Apr
[Reflexion of French experts on the key points of the symposium].
2002 Oct
[The challenge to treat hypertensive patients with type 2 diabetes].
2002 Oct
[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
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
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
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
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

JP3292732B2
20

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 [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
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 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
NDF-RT N0000175420
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
WHO-VATC QC03BA11
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
WHO-ATC C03BA11
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
NDF-RT N0000175359
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
LIVERTOX 503
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
WHO-ATC C09BX01
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
WHO-ATC C10BX13
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
WHO-VATC QC09BX01
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
Code System Code Type Description
DRUG CENTRAL
1433
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
ECHA (EC/EINECS)
248-012-7
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
WIKIPEDIA
INDAPAMIDE
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
MERCK INDEX
M6245
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY Merck Index
MESH
D007190
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
IUPHAR
7203
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
PUBCHEM
3702
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
FDA UNII
F089I0511L
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
EPA CompTox
DTXSID7044633
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
DAILYMED
F089I0511L
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
LACTMED
Indapamide
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
ChEMBL
CHEMBL406
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
RS_ITEM_NUM
1338801
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
NSC
757075
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
CHEBI
5893
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
EVMPD
SUB08169MIG
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
NCI_THESAURUS
C29119
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
CAS
26807-65-8
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
INN
3333
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
RXCUI
5764
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY RxNorm
DRUG BANK
DB00808
Created by admin on Fri Dec 16 21:34:58 UTC 2022 , Edited by admin on Fri Dec 16 21:34:58 UTC 2022
PRIMARY
ACTIVE MOIETY
Structure of INDAPAMIDE
SALT/SOLVATE (PARENT)
Structure of INDAPAMIDE HEMIHYDRATE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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