INDAPAMIDE HEMIHYDRATE

Details

Stereochemistry	RACEMIC
Molecular Formula	2C16H16ClN3O3S.H2O
Molecular Weight	749.684
Optical Activity	( + / - )
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.CC1CC2=CC=CC=C2N1NC(=O)C3=CC(=C(Cl)C=C3)S(N)(=O)=O.CC4CC5=CC=CC=C5N4NC(=O)C6=CC(=C(Cl)C=C6)S(N)(=O)=O

InChI

InChIKey=GPFKQEHXQLDCEK-UHFFFAOYSA-N

InChI=1S/2C16H16ClN3O3S.H2O/c2*1-10-8-11-4-2-3-5-14(11)20(10)19-16(21)12-6-7-13(17)15(9-12)24(18,22)23;/h2*2-7,9-10H,8H2,1H3,(H,19,21)(H2,18,22,23);1H2

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Sources: http://www.drugbank.ca/drugs/DB00808
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Voltage-gated potassium channel subunit Kv7.1 3 Target ID: CHEMBL1866 Sources: http://www.drugbank.ca/drugs/DB00808	Inhibitor 8504
Voltage-gated potassium channel beta subunit Mink 3 Target ID: CHEMBL4872 Sources: http://www.drugbank.ca/drugs/DB00808	Inhibitor 8504
Carbonic anhydrase IX 36 Target ID: CHEMBL3594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19119014	Inhibitor 8504	36.0 nM [Ki]
Carbonic anhydrase XII 30 Target ID: CHEMBL3242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19119014	Inhibitor 8504	10.0 nM [Ki]
Carbonic anhydrase VII 35 Target ID: CHEMBL2326 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19119014	Inhibitor 8504	0.23 nM [Ki]
Thiazide-sensitive sodium-chloride cotransporter 28 Target ID: CHEMBL1876 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D00345	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Congestive heart failure 54 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/98/75-105_Indapamide_prntlbl.pdf	Primary		Approved 8583	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
Hypertension 575 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/98/75-105_Indapamide_prntlbl.pdf	Primary		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
260 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/018538s028lbl.pdf	5 mg single, oral dose: 5 mg 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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
14 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/018538s028lbl.pdf	5 mg single, oral dose: 5 mg 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

F_unbound

Value	Dose	Co-administered	Analyte	Population
25% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/018538s028lbl.pdf	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:		INDAPAMIDE blood	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse 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	unhealthy, 21 - 73 Health Status: unhealthy Age Group: 21 - 73 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6346848	Disc. AE: Hypokalemia... AEs leading to discontinuation/dose reduction: Hypokalemia (0.64%) Sources: https://pubmed.ncbi.nlm.nih.gov/6346848

AEs

AE	Significance	Dose	Population
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	unhealthy, 21 - 73 Health Status: unhealthy Age Group: 21 - 73 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/6346848

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193		inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT3 747 OATP1B3 961	CYP2C19 1119 CYP2C8 810	CYP2C23 12 CYP4A1 17

Drug as perpetrator

Target	Modality	Activity
CYP4A1 25	inducer 1966 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3716319/	no
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17314201/	yes [IC50 11 uM]
OATP1B3 970	inhibitor 4027 Sources: https://molpharm.aspetjournals.org/content/83/6/1257	yes [Inhibition 10 uM]
CYP2C23 12	inducer 1966 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3716319/	yes

Drug as victim

Target	Modality	Activity
CYP3A4 1946	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2645476/	major
CYP2C19 1119	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2645476/	yes
CYP2C8 810	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2645476/	yes
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/22579001/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/7923634/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5893	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5893
ChemicalBook	CB2420420	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2420420
eMolecules	539574	https://www.emolecules.com/cgi-bin/more?vid=539574
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

PubMed

Title	Date	PubMed
Optimization of a solid-phase extraction method for determination of indapamide in biological fluids using high-performance liquid chromatography.	2003-05-05	12668086
Effect of low-dose perindopril/indapamide on albuminuria in diabetes: preterax in albuminuria regression: PREMIER.	2003-05	12654706
Drug-drug interactions among elderly patients hospitalized for drug toxicity.	2003-04-02	12672733
Cardiovascular protective role of a low-dose antihypertensive combination in obese Zucker rats.	2003-03	12640256
Effects of a perindopril-based blood pressure lowering regimen on cardiac outcomes among patients with cerebrovascular disease.	2003-03	12633548
Progress and stroke--it's time to translate evidence into action.	2003-02-01	12557875
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.	2003-02	12574793
Prevention of stone formation and bone loss in absorptive hypercalciuria by combined dietary and pharmacological interventions.	2003-02	12544288
[Secondary prevention after ischemic stroke].	2003-01-29	12643070
Regression of left ventricular hypertrophy with echocardiography: some lessons from the LIVE study.	2003-01	12544454
Converting enzyme inhibitor or AT1-receptor blocker for decreasing long-term mortality in patients with stroke history and renal dysfunction?	2003-01	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.	2003-01	12500017
The Perindopril Protection Against Recurrent Stroke Study (PROGRESS): clinical implications for older patients with cerebrovascular disease.	2003	12641480
Effects of four antihypertensive monotherapies on cardiac mass and function in hypertensive patients with left ventricular hypertrophy: randomized prospective study.	2002-12	12476475
Hypokalaemia and hyponatraemia due to indapamide.	2002-12	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.	2002-12	12438525
[Indapamide-induced pemphigus foliaceus a sulfurous affair?].	2002-11-21	12442120
Drug-induced long QT in isolated rabbit Purkinje fibers: importance of action potential duration, triangulation and early afterdepolarizations.	2002-10-04	12354568
[Reflexion of French experts on the key points of the symposium].	2002-10	12356003
[The challenge to treat hypertensive patients with type 2 diabetes].	2002-10	12356002
[Treatment of hypertensive type 2 diabetes patients with microalbuminuria].	2002-10	12356001
[Arterial hypertension in elderly individuals].	2002-10	12356000
[Management of hypertensive patients with left ventricular hypertrophy].	2002-10	12355999
Water vapor absorption into amorphous hydrophobic drug/poly(vinylpyrrolidone) dispersions.	2002-10	12226842
[Coversyl again].	2002-09-09	12362877
Two derivative spectrophotometric determinations of indapamide in pharmaceutical dosage forms.	2002-09-05	12191722
[Hypertension and microcirculation].	2002-09	12407782
[Combination of low-dose perindopril/indapamide versus atenolol in the hypertensive patient. Effects on systolic pressure and arterial hemodynamics. REASON Study].	2002-09	12407781
Indapamide induced syncope in a patient with long QT syndrome.	2002-09	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.	2002-09	12214263
Dose-dependent prevention of fibrosis in aorta of salt-loaded stroke-prone spontaneously hypertensive rats by combined delapril and indapamide treatment.	2002-09	12198325
Fixed combinations of delapril plus indapamide vs fosinopril plus hydrochlorothiazide in mild to moderate essential hypertension.	2002-08-31	12201354
[Efficacy and tolerance of rilmenidine in patients with mild to moderate hypertension. Results of a Czech and Slovak 6-month multicenter study].	2002-08	12425202
[Arterial hypertension and tachycardia: monitoring the patient's personal drug therapy].	2002-08	12405021
Gender influence on the dose-ranging of a low-dose perindopril-indapamide combination in hypertension: effect on systolic and pulse pressure.	2002-08	12172328
Mechanisms of adrenergic control of sino-atrial node discharge.	2002-07-31	12595754
Hyponatraemia and hypokalaemia caused by indapamide.	2002-07-01	12088485
Comparison of indapamide and low-dose hydrochlorothiazide monotherapy in black patients with mild to moderate hypertension.	2002-07	12197195
[Pigmented lesions secondary to indapamide].	2002-07	12162228
[PROGRESS--a trial on blood pressure lowering after stroke and TIA. ACE inhibitors and diuretics reduce the risk of new stroke].	2002-05-16	12082946
Stroke prevention: management of modifiable vascular risk factors.	2002-05	12021938
Hyponatraemia and hypokalaemia due to indapamide.	2002-03-04	11999238
[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
Effects of antihypertensive therapy on hemorheological profiles in female hypertensive patients with initially low or high whole blood viscosity.	2002	12082261
The effects of the addition of micronised fenofibrate on uric acid metabolism in patients receiving indapamide.	2002	12017210
[CEA comprehensive evaluation for Western and traditional Chinese hypotensive drugs].	2001-09	12575552
Indapamide-induced pemphigus foliaceus.	2001-09	12243711
Antihypertensive action of indapamide. Comparative studies in several experimental models.	1975-10	1243026

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 `Mon Mar 31 22:29:57 GMT 2025` Edited by `admin` on `Mon Mar 31 22:29:57 GMT 2025`
Record UNII	W0LY35K007
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

INDAPAMIDE HEMIHYDRATE

Common Name

English

TENAXIL

Preferred Name

English

BENZAMIDE, 3-(AMINOSULFONYL)-4-CHLORO-N-(2,3-DIHYDRO-2-METHYL-1H-INDOL-1-YL)-, HYDRATE (2:1)

Systematic Name

English

4-CHLORO-N-(2-METHYL-2,3-DIHYDRO-1H-INDOL-1-YL)-3-SULFAMOYLBENZAMIDE HYDRATE (2:1)

Systematic Name

English

D06401

Code

English

Indapamide hemihydrate [WHO-DD]

Common Name

English

INDAPAMIDE HYDRATE

Common Name

English

Code System Code Type Description

FDA UNII

W0LY35K007