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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=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

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

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
[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
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
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
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
Coversyl plus--when monotherapy is not enough.
2001 Jun-Jul
Antihypertensive drug prescription trends at the primary health care centres in Bahrain.
2001 May
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
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
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 and tolerance of rilmenidine in patients with mild to moderate hypertension. Results of a Czech and Slovak 6-month multicenter study].
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
Hypokalaemia and hyponatraemia due to indapamide.
2002 Dec
Hyponatraemia and hypokalaemia caused by indapamide.
2002 Jul 1
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
[Hypertension and microcirculation].
2002 Sep
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
Regression of left ventricular hypertrophy with echocardiography: some lessons from the LIVE study.
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

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 Tue Oct 22 00:33:48 UTC 2019
Edited
by admin
on Tue Oct 22 00:33:48 UTC 2019
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 [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
Related Record Type Details
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY