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Chlortalidone

Chlortalidone Structure
Chlortalidone
  • CAS No.77-36-1
  • Chemical Name:Chlortalidone
  • CBNumber:CB3233539
  • Molecular Formula:C14H11ClN2O4S
  • Formula Weight:338.77
  • MOL File:77-36-1.mol
Chlortalidone Property
Safety
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H315-H319-H335
  • Precautionary statements P261-P264-P271-P280-P302+P352-P305+P351+P338
Chlortalidone Price More Price(2)
  • Brand: Sigma-Aldrich(India)
  • Product number: SML0591
  • Product name : Chlorthalidone
  • Purity: ≥98% (HPLC)
  • Packaging: 5MG
  • Price: ₹6235.2
  • Updated: 2022/06/14
  • Buy: Buy
  • Brand: Sigma-Aldrich(India)
  • Product number: SML0591
  • Product name : Chlorthalidone
  • Purity: ≥98% (HPLC)
  • Packaging: 25MG
  • Price: ₹25352.15
  • Updated: 2022/06/14
  • Buy: Buy

Chlortalidone Chemical Properties,Usage,Production

  • Chemical Properties Chlortalidone is White Solid
  • Originator Hygroton, Geigy, US ,1960
  • Uses In terms of activity, chlorothalidone is very similar to benzothiadiazide (21.3.13) and is used as an independent drug or in combination with other antihypertensive agents for lowering arterial blood pressure, and also as an adjuvant drug for treating edema caused by cardiac insufficiency and renal irregularities, including nephrotic syndrome.
  • Uses Antihypertensive Agents,Diuretics,Sodium Chloride Symporter Inhibitors
  • Uses Chlorthalidone is used as a diuretic; antihypertensive.
  • Definition ChEBI: Chlorthalidone is a sulfonamide, a member of isoindoles and a member of monochlorobenzenes.
  • Manufacturing Process 15 parts of aqueous 46% sodium nitrite solution are gradually added to a mixture of 27.5 parts of 4-chloro-3-amino-benzophenone-2'-carboxylic acid, 200 parts of glacial acetic acid and 20 parts of 37% hydrochloric acid at 0° to 10°C. The solution of the diazonium salt is poured into an ice-cooled mixture of 200 parts of 30% sulfur dioxide solution in glacial acetic acid and 3 parts of crystallized cupric chloride in 15 parts of water. Nitrogen is developed and, after a short time, the 4-chloro-2'-carboxy-benzophenone-3-sulfochloride crystallizes out. After 1 hour it is filtered off and washed with water. MP 178° to 182°C.
    35.9 parts of 4-chloro-2'-carboxy-benzophenone-3-sulfochloride and 50 parts of thionyl chloride are heated first for 3 hours at 30° to 35°C and then for 1 hour at 45°C. The excess thionyl chloride is distilled off in the vacuum, the dichloride, 3-chloro-3-(3'-chlorosulfonyl-4'-chlorophenyl)phthalide, which remains as a crystallized mass is dissolved in 150 parts of chloroform and a mixture of 200 parts of 25% aqueous ammonia solution and 200 parts of ethanol is added dropwise at about 10°C while stirring and cooling. After stirring for 1 hour at 40°C, the solvent is distilled off in the vacuum and diluted hydro chloric acid is added to the residue whereupon the 1-oxo-3-(3'- sulfamyl-4'-chloro-phenyl)3-hydroxy-isoindoline which is tautomeric to the 4- chloro-2'-carbamyl-benzophenone-3-sulfonamide, separates out. On recrystallizing from diluted ethanol, the isoindoline derivative melts at 215°C on decomposition.
    Instead of reacting the dichloride in aqueous solution with ammonia, it can also be reacted at -50° to -40°C with a great excess of liquid ammonia. After removal of the ammonia, the crude product obtained is recrystallized as described above.
  • brand name Hygroton (Sanofi Aventis); Thalitone (Monarch).
  • Therapeutic Function Diuretic, Antihypertensive
  • Biochem/physiol Actions Chlorthalidone is a thiazide-like diuretic, an inhibitor of the Na+-Cl- cotransporter. Chlorthalidone inhibits sodium ion transport across the renal tubular epithelium increasing the delivery of sodium to the distal renal tubule and indirectly increasing potassium excretion via the sodium-potassium exchange mechanism. Chlorthalidone also promotes Ca++ reabsorption by an unknown mechanism. Several recent comparison studies inidcate that chlorthalidone may be a better drug in preventing cardiovascular events than hydrochlorothiazide.
  • Clinical Use Chlorthalidone has a long duration of action (48–72 hours). Although quinethazone and metolazone are administered daily, chlorthalidone may be administered in doses of 25 to 100 mg three times a week. When chlorthalidone is formulated with the excipient povidone, the product, Thalitone, has greater bioavailability (>90%) and reaches peak plasma concentrations in a shorter time compared with its other products. Similar to the quinazolinones, it also is extensively bound to carbonic anhydrase in the erythrocytes.
  • Synthesis Chlorothalidone, 2-chloro-5-(1-hydroxy-3-oxo-1-isoindolinyl)benzolsulfamide (21.3.26), is synthesized by two proposed methods from 2-carboxy-4-chlorobenzophenone (21.3.21), which is easily synthesized by acylating chlorobenzol with phthalic anhydride in the presence of aluminum chloride. The resulting benzophenone (21.3.21) undergoes nitration by nitric acid, which gives 2-carboxy-3-nitro-4-chlorobenzophenone (21.3.22). The nitro group in the resulting compound is reduced by tin dichloride to 2- carboxy-3-amino-4-chlorobenzophenone (21.3.23). Next, subsequent diazotation and reaction with sulfur dioxide in the presence of copper dichloride gives the corresponding sulfonylchloride (21.3.24). Upon reaction with thionyl chloride, this compound undergoes cyclization into phtahlide (21.3.25), which when reacted with aqueous ammonia rearranges into a derivative of isoindoline with simultaneous substitution of the chloride atom in the sulfogroup with an amino group, which results in chlorothalidone (21.3.26).

    Synthesis_77-36-1

  • 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 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 Chlortalidone is highly bound to red blood cells; the receptor to which it is bound has been identified as carbonic anhydrase. It is much less strongly bound to plasma proteins.
    Chlortalidone is mainly excreted unchanged in the urine.
Chlortalidone Preparation Products And Raw materials
Raw materials
Preparation Products
Chlortalidone Suppliers
Global(253)Suppliers
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Chlortalidone Spectrum
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  • C14H11ClN2O4S
  • 氯塞酮/用于峰鉴别试验
  • 氯噻酮-[13C6]/精确称量
  • 甲醇中氯噻酮
  • PERFEMIKER]氯塞酮,98%
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  • 氯噻酮
  • 氯塞酮(氯噻酮)
  • 氯塞酮/2-氯-5-(2,3-二氢-1-羟基-3-氧代-1H-异吲哚-1-基)苯磺酰胺
  • 氯塞酮
  • 2-氯-5-(2,3-二氢-1-羟基-3-氧代-1H-异吲哚-1-基)苯磺酰胺
  • 77-36-1
  • Chlorthalidone - Bio-X ?
  • Chlorthalidone in Methanol
  • Clorthalidone Reference Standard
  • Chlorthalidone API
  • Chlortalidone 2-Chloro-5-(1-hydroxy-3-oxo-1- isoindolinyl)benzenesulfonamide
  • 2-chloro-5-(1-hydroxy-3-oxo-2H-isoindol-1-yl)benzenesulfonamide (chlorotalidone)
  • 2-c h loro-5-[(1RS)-1-h yd roxy-3-oxo-2,3-d i h yd ro-1h -i soi nd ol-1-yl]b e nze ne sulf ona mi d e

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