INDAPAMIDE

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 Search

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

Targets

Primary Target	Pharmacology	Condition	Potency
Carbonic anhydrase XII 28	Inhibitor 7468	Heart Failure	10.0 nM [Ki]
Voltage-gated potassium channel subunit Kv7.1 3	Inhibitor 7468	Heart Failure
Voltage-gated potassium channel beta subunit Mink 3	Inhibitor 7468	Heart Failure
Carbonic anhydrase IX 33	Inhibitor 7468	Heart Failure	36.0 nM [Ki]
Carbonic anhydrase VII 34	Inhibitor 7468	Heart Failure	0.23 nM [Ki]
Thiazide-sensitive sodium-chloride cotransporter 23	Inhibitor 7468	Heart Failure

Conditions

Condition	Modality	Targets	Highest Phase	Product
Heart Failure 148	Primary	Voltage-gated potassium channel subunit Kv7.1 Voltage-gated potassium channel beta subunit Mink Thiazide-sensitive sodium-chloride cotransporter Carbonic anhydrase IX Carbonic anhydrase XII Carbonic anhydrase VII	Approved 7883	Indapamide
Hypertension 567	Primary	Voltage-gated potassium channel subunit Kv7.1 Voltage-gated potassium channel beta subunit Mink Thiazide-sensitive sodium-chloride cotransporter Carbonic anhydrase IX Carbonic anhydrase XII Carbonic anhydrase VII	Approved 7883	Indapamide
Calcium nephrolithiasis 2			Approved (off-label) 8

PubMed

Title	Date	PubMed
Antihypertensive action of indapamide. Comparative studies in several experimental models.	1975 Oct	1243026
[Effects of perindopril and its combination with indapamide on risk stratification in patients with hypertension].	2001	11642074
Perindopril/indapamide 2/0.625 mg/day: a review of its place in the management of hypertension.	2001	11465878
Indapamide plus perindopril--simpler treatment, better compliance.	2001 Apr-May	11474694
Comparison of spectrophotometric and an LC method for the determination perindopril and indapamide in pharmaceutical formulations.	2001 Aug	11451641
Recommendations for the use of low-dose diuretics.	2001 Aug-Sep	11766618
Academic support for combination therapy in hypertension.	2001 Aug-Sep	11766616
The lowering of blood pressure after stroke.	2001 Dec 8	11747948
The lowering of blood pressure after stroke.	2001 Dec 8	11747946
The lowering of blood pressure after stroke.	2001 Dec 8	11747943
Indapamide, a thiazide-like diuretic, decreases bone resorption in vitro.	2001 Feb	11204436
[New fixed combination for therapy of hypertension. "Softener" and "stimulant" supplement each other].	2001 Feb 1	11234524
Celecoxib-induced cholestatic hepatitis.	2001 Feb 6	11177350
Coversyl plus--when monotherapy is not enough.	2001 Jun-Jul	11710312
Antihypertensive drug prescription trends at the primary health care centres in Bahrain.	2001 May	11501335
Amelioration of arterial properties with a perindopril-indapamide very-low-dose combination.	2001 Nov	11848258
[Clinical study of the month. Secondary prevention of cerebrovascular accident with perindopril: the PROGRESS study].	2001 Nov	11789395
Indapamide-induced pemphigus foliaceus.	2001 Sep	12243711
[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
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
Cutaneous drug reaction case reports: from the world literature.	2002	11978142
[Efficacy and tolerance of rilmenidine in patients with mild to moderate hypertension. Results of a Czech and Slovak 6-month multicenter study].	2002 Aug	12425202
Gender influence on the dose-ranging of a low-dose perindopril-indapamide combination in hypertension: effect on systolic and pulse pressure.	2002 Aug	12172328
[Indapamide-induced pemphigus foliaceus a sulfurous affair?].	2002 Aug-Sep	12442120
Hypokalaemia and hyponatraemia due to indapamide.	2002 Dec	12472097
Hyponatraemia and hypokalaemia caused by indapamide.	2002 Jul 1	12088485
Stroke prevention: management of modifiable vascular risk factors.	2002 May	12021938
[PROGRESS--a trial on blood pressure lowering after stroke and TIA. ACE inhibitors and diuretics reduce the risk of new stroke].	2002 May 16	12082946
[Hypertension and microcirculation].	2002 Sep	12407782
The Perindopril Protection Against Recurrent Stroke Study (PROGRESS): clinical implications for older patients with cerebrovascular disease.	2003	12641480
Drug-drug interactions among elderly patients hospitalized for drug toxicity.	2003 Apr 2	12672733
Regression of left ventricular hypertrophy with echocardiography: some lessons from the LIVE study.	2003 Jan	12544454
[Secondary prevention after ischemic stroke].	2003 Jan 29	12643070
Effect of low-dose perindopril/indapamide on albuminuria in diabetes: preterax in albuminuria regression: PREMIER.	2003 May	12654706
Optimization of a solid-phase extraction method for determination of indapamide in biological fluids using high-performance liquid chromatography.	2003 May 5	12668086

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

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Name

Type

Language

INDAPAMIDE

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