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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
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

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
Antihypertensive action of indapamide. Comparative studies in several experimental models.
1975 Oct
[CEA comprehensive evaluation for Western and traditional Chinese hypotensive drugs].
2001 Sep
Indapamide-induced pemphigus foliaceus.
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
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
[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
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
[The challenge to treat hypertensive patients with type 2 diabetes].
2002 Oct
[Treatment of hypertensive type 2 diabetes patients with microalbuminuria].
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
[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
Dose-dependent prevention of fibrosis in aorta of salt-loaded stroke-prone spontaneously hypertensive rats by combined delapril and indapamide treatment.
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

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
Substance Class Chemical
Created
by admin
on Fri Dec 16 21:34:58 UTC 2022
Edited
by admin
on Fri Dec 16 21:34:58 UTC 2022
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
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
Related Record Type Details
Structure of INDAPAMIDE, (R)-
ENANTIOMER -> RACEMATE
Structure of INDAPAMIDE, (S)-
ENANTIOMER -> RACEMATE
Structure of INDAPAMIDE
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.
Structure of INDAPAMIDE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
Structure of INDAPAMIDE HEMIHYDRATE
SALT/SOLVATE -> PARENT
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
From 71 to 79% of the Lozol in plasma is reversibly bound to plasma proteins.
REVERSIBLE
Structure of INDAPAMIDE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
Structure of INDAPAMIDE HEMIHYDRATE
SOLVATE->ANHYDROUS
OAT-3
TRANSPORTER -> INHIBITOR
Related Record Type Details
Structure of METHYL 4-CHLORO-3-SULFAMOYLBENZOATE
METABOLITE -> PARENT
Related Record Type Details
Structure of DEHYDROINDAPAMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2-METHYLINDOLINE
IMPURITY -> PARENT
Structure of 1-AMINO-2-METHYLINDOLINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of DEHYDROINDAPAMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2-METHYL-1-NITROSO-2,3-DIHYDRO-1H-INDOLE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2-METHYL-1-NITROSO-2,3-DIHYDRO-1H-INDOLE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2-METHYLINDOLIN-1-AMINE HYDROCHLORIDE
IMPURITY -> PARENT
Related Record Type Details
Structure of INDAPAMIDE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC
NIH
NCATS
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