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Indapamide
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  • Name Indapamide
  • EINECS248-012-7
  • CAS No. 26807-65-8
  • Density1.51 g/cm3
  • PSA100.88000
  • LogP4.32040
  • SolubilitySoluble in ethanol. Insoluble in water
  • Melting Point160-162 °C
  • FormulaC16H16ClN3O3S
  • Boiling Point110.4°C (rough estimate)
  • Molecular Weight365.84
  • Flash PointN/A
  • Transport InformationN/A
  • AppearanceCrystalline solid
  • Safety
  • Risk CodesN/A
  • Molecular Structure
    Molecular Structure of 26807-65-8 (Indapamide)
  • Hazard SymbolsN/A
  • SynonymsN/A
  • Article Data8

Indapamide Synthetic route

63968-75-2

Dehydroindapamide

26807-65-8

Indapamide

Conditions
ConditionsYield
With sodium tetrahydroborate; hexachloroplatinic acid; hydrogen In ethanol at 10℃; for 1h;99.3%

N-amino-2-methylindoline hydrochloride

C8H5Cl2NO5S

26807-65-8

Indapamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 15℃; for 6h; Temperature; Solvent;96.89%
1205-30-7

4-chloro-3-sulphamoylbenzoic acid

6872-06-6

2-methyl indoline

26807-65-8

Indapamide

Conditions
ConditionsYield
Stage #1: 2-methyl indoline With triethylamine; hydroxylamine-O-sulfonic acid at 10℃;
Stage #2: 4-chloro-3-sulphamoylbenzoic acid With dicyclohexyl-carbodiimide at 15℃; for 6h; Reagent/catalyst;		95.5%

1-amino-2,3-dihydro-2-methyl-1H-indole mesylate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran80.5%
1205-30-7

4-chloro-3-sulphamoylbenzoic acid

31529-46-1

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

26807-65-8

Indapamide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In ethanol at -12 - -4℃; for 2h;70%

N-amino-2-methylindoline hydrochloride

70049-77-3

3-(aminosulfonyl)-4-chlorobenzoyl chloride

26807-65-8

Indapamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuranPurity (HPLC)
26807-65-8

Indapamide

592-82-5

butyl isothiocyanate

4-chloro-3-({[(butylamino)carbonothioyl]amino}sulfonyl)-N-(2-methyl-2,3-dihydro-1H-indole-1-yl)benzamide

Conditions
ConditionsYield
Stage #1: Indapamide With potassium carbonate In acetone for 0.5h; Reflux;
Stage #2: butyl isothiocyanate In acetone for 10h; Reflux;		87%
26807-65-8

Indapamide

2131-55-7

4-Chlorophenyl isothiocyanate

4-chloro-3-[({[(4-chlorophenyl)amino]carbonothioyl}amino)sulfonyl]-N-(2-methyl-2,3-dihydro-1H-indole-1-yl)benzamide

Conditions
ConditionsYield
Stage #1: Indapamide With potassium carbonate In acetone for 0.5h; Reflux;
Stage #2: 4-Chlorophenyl isothiocyanate In acetone for 10h; Reflux;		87%
26807-65-8

Indapamide

1544-68-9

4-fluorophenyl isothiocyanate

4-chloro-3-[({[(4-fluorophenyl)amino]carbonothioyl}amino)sulfonyl]-N-(2-methyl-2,3-dihydro-1H-indole-1-yl)benzamide

Conditions
ConditionsYield
Stage #1: Indapamide With potassium carbonate In acetone for 0.5h; Reflux;
Stage #2: 4-fluorophenyl isothiocyanate In acetone for 10h; Reflux;		85%
26807-65-8

Indapamide

2284-20-0

4-Methoxyphenyl isothiocyanate

4-chloro-3-[({[(4-methoxyphenyl)amino]carbonothioyl}amino)sulfonyl]-N-(2-methyl-2,3-dihydro-1H-indole-1-yl)benzamide

Conditions
ConditionsYield
Stage #1: Indapamide With potassium carbonate In acetone for 0.5h; Reflux;
Stage #2: 4-Methoxyphenyl isothiocyanate In acetone for 10h; Reflux;		78%

Indapamide Chemical Properties

Molecular Structure of Indapamide (CAS NO.26807-65-8):

IUPAC Name: 4-Chloro-N-(2-methyl-2,3-dihydroindol-1-yl)-3-sulfamoylbenzamide 
 Molecular Formula: C16H16ClN3O3S
Molecular Weight: 365.83
EINECS: 248-012-7  
Melting Point: 160-162 °C
Index of Refraction: 1.693
Molar Refractivity: 92.82 cm3
Molar Volume: 241.8 cm3
Surface Tension: 73.7 dyne/cm
Density: 1.51 g/cm3
Appearance: Crystalline Solid
Canonical SMILES: CC1CC2=CC=CC=C2N1NC(=O)C3=CC(=C(C=C3)Cl)S(=O)(=O)N
InChI: 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)
InChIKey: NDDAHWYSQHTHNT-UHFFFAOYSA-N
Classification Code: Antihypertensive; Antihypertensive agents; Cardiovascular Agents; Diuretic; Diuretics; Drug / Therapeutic Agent;; Natriuretic Agents; Reproductive Effect

Indapamide Uses

 Indapamide (CAS NO.26807-65-8) is a non-thiazide sulphonamide diuretic drug marketed by Servier, generally used in the treatment of hypertension, as well as decompensated cardiac failure.

Indapamide Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intraperitoneal 347mg/kg (347mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1491, 1975.
guinea pig LD50 intravenous 272mg/kg (272mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1491, 1975.
guinea pig LD50 oral > 3gm/kg (3000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1491, 1975.
mouse LD50 intraperitoneal 410mg/kg (410mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1491, 1975.
mouse LD50 intravenous 577mg/kg (577mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1491, 1975.
mouse LD50 oral > 3gm/kg (3000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1491, 1975.
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 1110, 1981.
rabbit LD50 intravenous 337mg/kg (337mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 1110, 1981.
rat LD50 intraperitoneal 393mg/kg (393mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1491, 1975.
rat LD50 intravenous 394mg/kg (394mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1491, 1975.
rat LD50 oral > 3gm/kg (3000mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 25, Pg. 1491, 1975.
rat LD50 subcutaneous > 5gm/kg (5000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 1110, 1981.

Indapamide Safety Profile

Poison by intravenous and intraperitoneal routes. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of Cl−, SOx, and NOx.

Indapamide Specification

 Indapamide (CAS NO.26807-65-8), its Synonyms are 3-(Aminosulfonyl)-4-chloro-N-(2,3-dihydro-2-methyl-1H-indol-1-yl)benzamide ; 4-Chloro-N-(2-methyl-1-indolinyl)-3-sulfamoylbenzamide ; Arifon ; Bajaten ; Cormil ; Damide ; Fludex ; Indaflex ; Indamol ; Indapamida ; Ipamix ; Lozol ; Natrilix ; Noranat ; Pressurai ; Benzamide, 3-(aminosulfonyl)-4-chloro-N-(2,3-dihydro-2-methyl-1H-indol-1-yl)- (9CI) ; Benzamide, 3-(aminosulfonyl)-4-chloro-N-(2,3-dihydro-2-methyl-1H-indol-l-yl)- ; Benzamide, 4-chloro-N-(2-methyl-1-indolinyl)-3-sulfamoyl- .

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