The Pharmacy of Chlorothiazide (6-Chloro-7-sulfamyl-1,2,4-benzothiadiazine-1,1-dioxide): A New Orally Effective Diuretic Agent**Merck Sharp &amp; Dohme Research Laboratories, Division of Merck &amp; Co., Inc., West Point, Pa

Charnicki, Walter F.; Bacher, Frederick A.; Freeman, Stewart A.; Decesare, Donald H.

doi:10.1002/jps.3030481114

Cited by 18 publications

(2 citation statements)

References 4 publications

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“…The concentrations obtained at the final three time points were the same and were averaged to give the saturated stoichiometric solubility (Anderson, Flora, 1996). All alkali solutions of CTZNa were analysed within one hour, as within this timeframe alkaline decomposition of the compound is insignificant (Charnicki et al, 1959).…”

Section: Solubilitymentioning

confidence: 99%

Preparation and solid state characterisation of chlorothiazide sodium intermolecular self-assembly suprastructure

Paluch

Tajber

McCabe

et al. 2010

European Journal of Pharmaceutical Sciences

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Please cite this article as: Paluch, K.J., Tajber, L., McCabe, T., O'Brien, J.E., Corrigan, O.I., Healy, A.M., Preparation and solid state characterisation of chlorothiazide sodium intermolecular self assembly suprastructure, European Journal of Pharmaceutical Sciences (2010Sciences ( ), doi:10.1016Sciences ( /j.ejps.2010 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Page 1 of 36A c c e p t e d M a n u s c r i p t A c c e p t e d M a n u s c r i p t 2 Abstract Chlorothiazide (CTZ), unlike other thiazide diuretics, can form salts. An injectable formulation containing the sodium salt is available; however neither the physicochemical characteristics of the salt nor its solid state form have been previously reported. This work reports on the crystal structure of chlorothiazide sodium. The structure was investigated by single crystal X-ray and nuclear magnetic spectroscopy (NMR) analyses and compared to chlorothiazide, while the solid state characteristics were assessed by thermal analysis, powder X-ray diffraction, infrared spectroscopy, dynamic moisture sorption and solubility analysis. The crystal structure of chlorothiazide sodium was determined to be triclinic; the crystal space group type was P-1. Chlorothiazide sodium presented a self-assembly polymeric-type suprastucture, where the unit cell comprised two chlorothiazide molecules bonded together with sodium cations through the water bridges. The coordinate centre comprised the following:The crystalline material was determined to be a monosodium dihydrate, stable in the range of 10-90% relative humidity (RH) at 25 ˚C. Additional processing of the salt resulted in a crystalline anhydrous form which was stable in the range 0-20% RH at 25 ˚C. The aqueous solubility of the chlorothiazide sodium dihydrate at 37 °C was found to be approximately 400-fold higher than that of chlorothiazide, which may present biopharmaceutical advantages for the salt compared to the non-salt form.

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Section: Solubilitymentioning

confidence: 99%

Preparation and solid state characterisation of chlorothiazide sodium intermolecular self-assembly suprastructure

Paluch

Tajber

McCabe

et al. 2010

European Journal of Pharmaceutical Sciences

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“…The aqueous solubility of CTZK dihydrate was estimated to be 78.71±1.82 mg/ml, 400-fold higher than that of CTZ (Charnicki et al 1959 A c c e p t e d M a n u s c r i p t …”

mentioning

confidence: 94%

Preparation and characterisation of novel chlorothiazide potassium solid-state salt forms: Intermolecular self assembly suprastructures

Paluch

Tajber

McCabe

et al. 2011

European Journal of Pharmaceutical Sciences

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Please cite this article as: Paluch, K.J., Tajber, L., McCabe, T., O'Brien, J.E., Corrigan, O.I., Healy, A.M., Preparation and characterisation of novel chlorothiazide potassium solid-state salt forms: intermolecular self assembly suprastructures., European Journal of Pharmaceutical Sciences (2010Sciences ( ), doi:10.1016Sciences ( /j.ejps.2010 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain.

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Neuere Entwicklungen auf dem Gebiet der quecksilberfreien Diuretica

Schlittler¹,

deStevens²,

Werner³

1962

Angewandte Chemie

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Quecksilberdiuretica sind noch heute das Mittel der Wahl, falls eine rasche und reichliche Diurese vonnoten ist. Quecksilber-Verbindungen sind jedoch tneist nur bei parenteraler Applikation wirksam, weshalb man immer wieder nach utoxischen, peroral wirksamen quecksilberfreien Prriparaten gesucht hut. In beinuhe idealer Weise entsprechen die Sulfonaniide diesen Bedingungen. Besonders wirksani sind Derivate des Chlorthiazids und Hydrochlorthiazids, die in dieseni Bericht ausfiihrlich b&hrieben werden. Daneben spielen Aldosteron-Antagonisten und Hemmer der Aldosteron-Ausscheidung vorerst nus eine geringeRolle.

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The Pharmacy of Chlorothiazide (6-Chloro-7-sulfamyl-1,2,4-benzothiadiazine-1,1-dioxide): A New Orally Effective Diuretic Agent**Merck Sharp & Dohme Research Laboratories, Division of Merck & Co., Inc., West Point, Pa

Cited by 18 publications

References 4 publications

Preparation and solid state characterisation of chlorothiazide sodium intermolecular self-assembly suprastructure

Preparation and solid state characterisation of chlorothiazide sodium intermolecular self-assembly suprastructure

Preparation and characterisation of novel chlorothiazide potassium solid-state salt forms: Intermolecular self assembly suprastructures

Neuere Entwicklungen auf dem Gebiet der quecksilberfreien Diuretica

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