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
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)
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 | ( + / - ) |
DescriptionSources: http://www.drugbank.ca/drugs/DB00808Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/dosage/indapamide.html
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1866 Sources: http://www.drugbank.ca/drugs/DB00808 |
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Target ID: CHEMBL4872 Sources: http://www.drugbank.ca/drugs/DB00808 |
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Target ID: CHEMBL3594 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19119014 |
36.0 nM [Ki] | ||
Target ID: CHEMBL3242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19119014 |
10.0 nM [Ki] | ||
Target ID: CHEMBL2326 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19119014 |
0.23 nM [Ki] | ||
Target ID: CHEMBL1876 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D00345 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Indapamide Approved UseIndapamide 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 Date1998 |
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Primary | Indapamide Approved UseIndapamide 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 Date1998 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
260 ng/mL |
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14 h |
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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
25% |
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: |
unhealthy, 21 - 73 |
Disc. AE: Hypokalemia... AEs leading to discontinuation/dose reduction: Hypokalemia (0.64%) Sources: |
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: |
unhealthy, 21 - 73 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes [IC50 11 uM] | ||||
yes [Inhibition 10 uM] | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
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Antihypertensive action of indapamide. Comparative studies in several experimental models. | 1975 Oct |
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Perindopril/indapamide 2/0.625 mg/day: a review of its place in the management of hypertension. | 2001 |
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Progress in reducing the burden of stroke. | 2001 Dec |
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The lowering of blood pressure after stroke. | 2001 Dec 8 |
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Antihypertensive drug prescription trends at the primary health care centres in Bahrain. | 2001 May |
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Functional consequences of the arrhythmogenic G306R KvLQT1 K+ channel mutant probed by viral gene transfer in cardiomyocytes. | 2001 May 15 |
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A double-blind trial of perindopril and nitrendipine in incipient diabetic nephropathy. | 2001 Oct |
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Improvement in blood pressure, arterial stiffness and wave reflections with a very-low-dose perindopril/indapamide combination in hypertensive patient: a comparison with atenolol. | 2001 Oct |
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[CEA comprehensive evaluation for Western and traditional Chinese hypotensive drugs]. | 2001 Sep |
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Blood pressure and stroke; the PROGRESS trial. | 2001 Sep |
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[Changes of distensibility of the aorta in elderly patients during long-term therapy with various classes of hypotensive drugs (magnetic resonance tomography data)]. | 2002 |
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[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 |
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[Clinical assessment of efficacy and safety of noliprel in patients with hypertension]. | 2002 |
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Effects of antihypertensive therapy on hemorheological profiles in female hypertensive patients with initially low or high whole blood viscosity. | 2002 |
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Cutaneous drug reaction case reports: from the world literature. | 2002 |
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[Efficacy and tolerance of rilmenidine in patients with mild to moderate hypertension. Results of a Czech and Slovak 6-month multicenter study]. | 2002 Aug |
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[Arterial hypertension and tachycardia: monitoring the patient's personal drug therapy]. | 2002 Aug |
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[Indapamide-induced pemphigus foliaceus a sulfurous affair?]. | 2002 Aug-Sep |
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Effects of four antihypertensive monotherapies on cardiac mass and function in hypertensive patients with left ventricular hypertrophy: randomized prospective study. | 2002 Dec |
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Hypokalaemia and hyponatraemia due to indapamide. | 2002 Dec |
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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 |
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The PROGRESS Trial: preventing strokes by lowering blood pressure in patients with cerebral ischemia. Emerging therapies: critique of an important advance. | 2002 Jan |
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Hyponatraemia and hypokalaemia due to indapamide. | 2002 Mar 4 |
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[PROGRESS--a trial on blood pressure lowering after stroke and TIA. ACE inhibitors and diuretics reduce the risk of new stroke]. | 2002 May 16 |
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[Reflexion of French experts on the key points of the symposium]. | 2002 Oct |
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[Treatment of hypertensive type 2 diabetes patients with microalbuminuria]. | 2002 Oct |
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Water vapor absorption into amorphous hydrophobic drug/poly(vinylpyrrolidone) dispersions. | 2002 Oct |
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[Hypertension and microcirculation]. | 2002 Sep |
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[Combination of low-dose perindopril/indapamide versus atenolol in the hypertensive patient. Effects on systolic pressure and arterial hemodynamics. REASON Study]. | 2002 Sep |
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Indapamide induced syncope in a patient with long QT syndrome. | 2002 Sep |
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[Coversyl again]. | 2002 Sep 9 |
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Progress and stroke--it's time to translate evidence into action. | 2002 Sep-Oct |
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The Perindopril Protection Against Recurrent Stroke Study (PROGRESS): clinical implications for older patients with cerebrovascular disease. | 2003 |
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Drug-drug interactions among elderly patients hospitalized for drug toxicity. | 2003 Apr 2 |
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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 |
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Prevention of stone formation and bone loss in absorptive hypercalciuria by combined dietary and pharmacological interventions. | 2003 Feb |
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Regression of left ventricular hypertrophy with echocardiography: some lessons from the LIVE study. | 2003 Jan |
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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 |
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Cardiovascular protective role of a low-dose antihypertensive combination in obese Zucker rats. | 2003 Mar |
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Effects of a perindopril-based blood pressure lowering regimen on cardiac outcomes among patients with cerebrovascular disease. | 2003 Mar |
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Mechanisms of adrenergic control of sino-atrial node discharge. | 2003 Mar-Apr |
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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
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/indapamide.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11204436
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
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on
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Record UNII |
F089I0511L
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Validated (UNII)
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NCI_THESAURUS |
C49185
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NDF-RT |
N0000175420
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QC03BA11
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C03BA11
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NDF-RT |
N0000175359
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LIVERTOX |
503
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WHO-ATC |
C09BX01
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C10BX13
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QC09BX01
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248-012-7
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INDAPAMIDE
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m6245
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D007190
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7203
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F089I0511L
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F089I0511L
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Indapamide
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SUB08169MIG
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C29119
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26807-65-8
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DB00808
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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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.
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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SALT/SOLVATE -> PARENT |
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BINDER->LIGAND |
From 71 to 79% of the Lozol in plasma is reversibly bound to plasma
proteins.
REVERSIBLE
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TRANSPORTER -> INHIBITOR | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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SOLVATE->ANHYDROUS |
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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.
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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