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HomeProduct name listIndapamide

Indapamide

Synonym(s):N-(4-Chloro-3-sulfamoylbenzamido)-2-methylindoline;Indapamide

  • CAS NO.:26807-65-8
  • Empirical Formula: C16H16ClN3O3S
  • Molecular Weight: 365.83
  • MDL number: MFCD00079375
  • EINECS: 248-012-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-22 14:21:17
Indapamide Structural

What is Indapamide?

Absorption

The bioavailability of indapamide is virtually complete after an oral dose and is unaffected by food or antacids. Indapamide is highly lipid-soluble due to its indoline moiety - a characteristic that likely explains why indapamide’s renal clearance makes up less than 10% of its total systemic clearance. The Tmax occurs approximately 2.3 hours after oral administration. The Cmax and AUC0-24 values are 263 ng/mL and 2.95 ug/hr/mL, respectively.

Toxicity

Indapamide overdose symptoms may include but are not limited to nausea, vomiting, gastrointestinal disorders, electrolyte disturbances and weakness. Other signs of overdose include respiratory depression and severe hypotension. In cases of overdose, supportive care interventions may be necessary to manage symptoms. Emesis and gastric lavage may be recommended to empty the stomach; however, patients should be monitored closely for any electrolyte or fluid imbalances.

Description

Indapamide is a derivative of benzolsulfonamide and its mechanism of action is analogous to that of thiazides. It is intended for lowering arterial blood pressure and as an adjuvant drug for treating edema caused by cardiac insufficiency.

Description

Indapamide (Item No. 21308) is an analytical reference standard that is categorized as a sulfonamide diuretic that blocks delayed-rectifier potassium currents. Formulations containing indapamide are used to treat hypertension, but it is abused by athletes to reduce body weight rapidly or mask the presence of other athletic-enhancing substances. Indapamide can be detected in urine. This product is intended for research and forensic applications.

Chemical properties

Crystalline Solid

Originator

Natrilix,Pharmacodex,W. Germany,1976

The Uses of Indapamide

Used as an antihypertensive. Diuretic

The Uses of Indapamide

diuretic, antihypertensive

The Uses of Indapamide

Used as an antihypertensive. Diuretic.

Background

The most significant modifiable risk factor for cardiovascular disease and the most prominent contributor to all-cause mortality is hypertension. Characterized by an office blood pressure of ≥140/90, hypertension is pervasive and impacts an estimated 25% of adults globally. Treatment for hypertension should include a number of lifestyle changes (ie. reduced sodium intake) along with pharmacotherapy - it should be noted that treatment with several antihypertensive agents may be required in order to achieve blood pressure targets.
Thiazide-like diuretics such as indapamide are a valuable tool for the treatment of hypertension and continue to grow in popularity, falling behind only ACE inhibitors in terms of prescription frequency. When compared to hydrochlorothiazide (another commonly prescribed diuretic), indapamide has been shown to be superior at lowering systolic blood pressure, reducing left ventricular mass index, lowering oxidative stress, inhibiting platelet aggregation, and reducing microalbuminuria associated with diabetes. Interestingly, unlike thiazide diuretics, several sources suggest that indapamide is not associated with glucose or lipid disturbances.
Indapamide is characterized by both a methylindoline and a sulfamoyl chlorobenzamide functional group, with the former being largely responsible for the molecule’s lipid solubility.

Indications

Indapamide is a diuretic indicated for use as monotherapy or in combination with other blood pressure-lowering agents to treat hypertension. It may also be used to treat fluid and salt retention associated with congestive heart failure.

What are the applications of Application

Indapamide is an NCCT inhibitor

Definition

ChEBI: A sulfonamide formed by condensation of the carboxylic group of 4-chloro-3-sulfamoylbenzoic acid with the amino group of 2-methyl-2,3-dihydro-1H-indol-1-amine.

Manufacturing Process

A total of 8.9 parts of 3-sulfamyl-4-chloro-benzoylchloride in a solution of 50 parts of anhydrous tetrahydrofuran are added portionwise in the course of 60 minutes, while stirring, to a solution of 5.2 parts of N-amino-2-methyl indoline and 3.5 parts of triethylamine in 150 parts of anhydrous tetrahydrofuran. The reaction mixture is left to stand 3 hours at room temperature, then the precipitated chiorhydrate of triethylamine is filtered off. The filtrate is evaporated under vacuum and the residue is crystallized from a solution of 60 parts of isopropanol in 75 parts of water. There are obtained 9 parts of N-(3- sulfamyl-4-chlorobenzamido)-2-methyl indoline, MP (K) 184° to 186°C, MP (MK) 160° to 162°C (isopropanol/water). [The melting points beingdetermined on a Kofler heater plate under the microscope (MK) or on a Kofler Bank (K)].

brand name

Lozol (Sanofi Aventis).

Therapeutic Function

Diuretic Indapamide

Pharmacokinetics

Classified as a sulfonamide diuretic, indapamide is an effective antihypertensive agent and by extension, has shown efficacy in the prevention of target organ damage. Administration of indapamide produces water and electrolyte loss, with higher doses associated with increased diuresis. Severe and clinically significant electrolyte disturbances may occur with indapamide use - for example, hypokalemia resulting from renal potassium loss may lead to QTc prolongation. Further electrolyte imbalances may occur due to renal excretion of sodium, chloride, and magnesium.
Other indapamide induced changes include increases in plasma renin and aldosterone, and reduced calcium excretion in the urine. In many studies investigating the effects of indapamide in both non-diabetic and diabetic hypertensive patients, glucose tolerance was not significantly altered. However, additional studies are necessary to assess the long term metabolic impacts of indapamide, since thiazide related impaired glucose tolerance can take several years to develop in non-diabetic patients.

Clinical Use

Indapamide is an effective diuretic drug when GFR falls below 40 mL/min. The duration of action is approximately 24 hours, with the normal oral adult dosage starting at 2.5 mg given each morning. The dose may be increased to 5.0 mg/day, but doses beyond this level do not appear to provide additional results.

Side Effects

Effects on urine content and side effects are similar to effects induced by thiazide diuretics.

Synthesis

Indapamide, 4-chloro-N-(2-methyl-1-indolinyl)-3-sulfamoylbenzamide (21.3.33), is synthesized from 2-methylendoline, the nitrosation of which gives 2-methyl- 1-nitrosoindoline (21.3.31). Reducing this with lithium aluminum hydride leads to formation of 1-amino-2-methylendoline (21.3.32). Acylating this with 3-sulfonylamino-4-chlorbenzoic acid chloride leads to (21.3.33).

Synthesis_26807-65-8

Drug interactions

Potentially hazardous interactions with other drugs
Analgesics: increased risk of nephrotoxicity with NSAIDs; antagonism of diuretic effect.
Anti-arrhythmics: hypokalaemia leads to increased cardiac toxicity; effects of lidocaine and mexiletine antagonised.
Antibacterials: avoid administration with lymecycline.
Antidepressants: increased risk of hypokalaemia with reboxetine; enhanced hypotensive effect with MAOIs; increased risk of postural hypotension with tricyclics.
Antiepileptics: increased risk of hyponatraemia with carbamazepine.
Antifungals: increased risk of hypokalaemia with amphotericin.
Antihypertensives: enhanced hypotensive effect; increased risk of first dose hypotension with postsynaptic alpha-blockers like prazosin; hypokalaemia increases risk of ventricular arrhythmias with sotalol.
Antipsychotics: hypokalaemia increases risk of ventricular arrhythmias with amisulpride; enhanced hypotensive effect with phenothiazines; hypokalaemia increases risk of ventricular arrhythmias with pimozide - avoid.
Atomoxetine: hypokalaemia increases risk of ventricular arrhythmias.
Cardiac glycosides: increased toxicity if hypokalaemia occurs.
Ciclosporin: increased risk of nephrotoxicity and possibly hypomagnesaemia.
Cytotoxics: increased risk of ventricular arrhythmias due to hypokalaemia with arsenic trioxide; increased risk of nephrotoxicity and ototoxicity with platinum compounds.
Lithium excretion reduced (increased toxicity).

Metabolism

As a result of extensive metabolism in the liver, the majority of indapamide excreted is metabolized, with only 7% remaining unchanged. In humans, as many as 19 distinct indapamide metabolites may be produced, although not all have been identified.
There are several metabolic routes through which indapamide may be metabolized, and CYP3A4 is the main enzyme involved in the corresponding hydroxylation, carboxylation, and dehydrogenation reactions.
Indapamide can undergo dehydrogenation to form M5, then oxidation to form M4, then further hydroxylation at the indole moiety to form M2. These reactions are facilitated by CYP3A4.
Another route of metabolism occurs when indapamide is first hydroxylated to M1 by CYP3A4. M1 then undergoes dehydrogenation to form M3 and is further oxidized to form M2. Hydroxylation of indapamide’s indole moiety is thought to form the major metabolite (M1), which is less pharmacologically active compared to its parent compound according to animal studies.
Indapamide may also undergo epoxidation via CYP3A4 to form a reactive epoxide intermediate. The unstable epoxide intermediate may then undergo dihydroxylation via microsomal epoxide hydrolase to form M6, or glutathione conjugation to form M7.

Metabolism

Indapamide is strongly bound to red blood cells, and is taken up by the vascular wall in smooth vascular muscle according to its high lipid solubility. 60-70% of a single oral dose is eliminated by the kidneys and 23% by the gastrointestinal tract. Indapamide is extensively metabolised with 5-7% of unchanged drug found in the urine during the 48 hours following administration. About 16-23% of dose is excreted in the faeces

Properties of Indapamide

Melting point: 160-162°C
Boiling point: 110.4°C (rough estimate)
alpha  -0.8~+0.8°(D/20℃) (c=5, C2H5OH)
Density  1.2895 (rough estimate)
refractive index  1.6100 (estimate)
storage temp.  -20°C Freezer
solubility  Practically insoluble in water, soluble in ethanol (96 per cent).
form  neat
form  Solid
pka pKa (25°) 8.8 ± 0.2
color  White to Off-White
Water Solubility  Soluble in ethanol. Insoluble in water
Merck  14,4935
CAS DataBase Reference 26807-65-8(CAS DataBase Reference)
EPA Substance Registry System Benzamide, 3-(aminosulfonyl)-4-chloro-N-(2,3-dihydro-2-methyl-1H-indol-1-yl)- (26807-65-8)

Safety information for Indapamide

Signal word Warning
Pictogram(s)
ghs
Health Hazard
GHS08
GHS Hazard Statements H362:Reproductive toxicity, effects on or via lactation
Precautionary Statement Codes P202:Do not handle until all safety precautions have been read and understood.
P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P263:Avoid contact during pregnancy/while nursing.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for Indapamide

InChIKey NDDAHWYSQHTHNT-UHFFFAOYSA-N

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