Indapamide

Base Information

• Chemical Name: Indapamide
• CAS No.: 26807-65-8
• Deprecated CAS: 49564-58-1
• Molecular Formula: C16H16ClN3O3S
• Molecular Weight: 365.84
• Hs Code.: 2935904000
• European Community (EC) Number: 248-012-7
• NSC Number: 757075
• UNII: F089I0511L
• DSSTox Substance ID: DTXSID7044633
• Nikkaji Number: J10.425F
• Wikipedia: Indapamide
• Wikidata: Q1078392
• NCI Thesaurus Code: C29119
• RXCUI: 5764
• Pharos Ligand ID: A752MF4ZP2H1
• Metabolomics Workbench ID: 43099
• ChEMBL ID: CHEMBL406
• Mol file: 26807-65-8.mol

Synonyms:Indapamide;Metindamide;S 1520;S-1520;S1520;SE 1520;SE-1520;SE1520

Chemical Property of Indapamide

Chemical Property:

• Appearance/Colour: Crystalline solid
• Melting Point: 160-162 °C
• Refractive Index: 1.693
• Boiling Point: 110.4°C (rough estimate)
• PKA: pKa (25°) 8.8 ± 0.2
• PSA: 100.88000
• Density: 1.51 g/cm³
• LogP: 4.32040
• Storage Temp.: -20°C Freezer
• Solubility.: Practically insoluble in water, soluble in ethanol (96 per cent).
• Water Solubility.: Soluble in ethanol. Insoluble in water
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 365.0600902
• Heavy Atom Count: 24
• Complexity: 580

Purity/Quality:

99% ,99.9%, ^*data from raw suppliers

racIndapamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2=CC=CC=C2N1NC(=O)C3=CC(=C(C=C3)Cl)S(=O)(=O)N
• Recent ClinicalTrials: Zilebesiran as Add-on Therapy in Patients With Hypertension Not Adequately Controlled by a Standard of Care Antihypertensive Medication (KARDIA-2)
• Recent EU Clinical Trials: Evaluation of the clinical efficacy and safety of perindopril 10 mg/indapamide 2.5 mg/amlodipine 5 or 10 mg/bisoprolol 5 mg in single-pill combination after 8 weeks of treatment versus the free combination of perindopril 10 mg, indapamide 2.5 mg and amlodipine 5 or 10 mg in patients with uncontrolled essential hypertension. An international, multicentre, randomised, double-blind, 16-week study.
• Recent NIPH Clinical Trials: Effects of the combination therapy of irbesartan and indapamide in chronik kidney disease with hypertension
• Uses: For the treatment of mild to moderate essential hypertension. Used as an antihypertensive. Diuretic diuretic, antihypertensive Used as an antihypertensive. Diuretic.
• 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. 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.
• Therapeutic Function: Diuretic Indapamide
• 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.
• 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).

Technology Process of Indapamide

There total 7 articles about Indapamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.3%

Dehydroindapamide (63968-75-2) → Indapamide (26807-65-8,77083-52-4)

Guidance literature:

With sodium tetrahydroborate; hexachloroplatinic acid; hydrogen; In ethanol; at 10 ℃; for 1h;

Reference yield: 96.89%

N-amino-2-methylindoline hydrochloride + C8H5Cl2NO5S → Indapamide (26807-65-8,77083-52-4)

Guidance literature:

With triethylamine; In dichloromethane; at 15 ℃; for 6h; Temperature; Solvent;

Reference yield: 95.5%

4-chloro-3-sulphamoylbenzoic acid (1205-30-7) + 2-methyl indoline (6872-06-6) → Indapamide (26807-65-8,77083-52-4)

Guidance literature:

2-methyl indoline; With triethylamine; hydroxylamine-O-sulfonic acid; at 10 ℃;

4-chloro-3-sulphamoylbenzoic acid; With dicyclohexyl-carbodiimide; at 15 ℃; for 6h; Reagent/catalyst;

upstream raw materials:

4-chloro-3-sulphamoylbenzoic acid

1-amino-2,3-dihydro-2-methylindole

3-(aminosulfonyl)-4-chlorobenzoyl chloride

pyrographite

Downstream raw materials:

C₈Cl₂N₂O₂*C₁₆H₁₆ClN₃O₃S

Refernces

• 1、 -. "Synthesis method of indapamide". Paragraph 0042-0049. . Retrieved 2021/01/11.
• 2、 -. "Indapamide synthetic method". Paragraph 0027; 0028. . Retrieved 2016/10/17.