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C4911

Sigma-Aldrich

Chlorothiazide

thiazide diuretic

Synonym(s):

6-Chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide

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About This Item

Empirical Formula (Hill Notation):
C7H6ClN3O4S2
CAS Number:
58-94-6
Molecular Weight:
295.72
EC Number:
200-404-9
MDL number:
MFCD00058576
UNSPSC Code:
12352202
PubChem Substance ID:
24278150
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

100

Assay

≥98% (HPLC)

form

powder

mp

>300 °C

solubility

DMF: 50 mg/mL, clear, colorless to very faintly yellow

storage temp.

2-8°C

SMILES string

O=S(C1=C2C=C(Cl)C(S(N)(=O)=O)=C1)(NC=N2)=O

InChI

1S/C7H6ClN3O4S2/c8-4-1-5-7(2-6(4)16(9,12)13)17(14,15)11-3-10-5/h1-3H,(H,10,11)(H2,9,12,13)

InChI key

JBMKAUGHUNFTOL-UHFFFAOYSA-N

Gene Information

human ... CA1(759) , CA4(762) , SLC12A3(6559)

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General description

Chlorothiazide (CTLD) is a thiazide-like diuretics and has antihypertensive effects.

Application

Chlorothiazide has been used as a reference standard in parallel artificial membrane permeability assay (PAMPA). It has also been used to test its effect on blocking pendrin activity.
One of the first in the thiazide class of diuretics.

Biochem/physiol Actions

Chlorothiazide (CTLD) shows structural resemblance with hydrochlorothiazide by having a sulfonamide group, but exhibits a long action duration. CTLD is an inhibitor of carbonic anhydrase and is more potent than hydrochlorothiazide.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Stela Dineva et al.
Journal of human hypertension, 33(11), 766-774 (2019-10-09)
Hypertension is a complex syndrome of multiple hemodynamic, neuroendocrine, and metabolic abnormalities. The goals of treatment in hypertension are to optimally control high blood pressure and to reduce associated cardiovascular morbidity and mortality using the most suitable therapy available. Hydrochlorothiazide
Emanuele Bernardinelli et al.
Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology, 38(5), 1984-1998 (2016-05-11)
Pendrin is a Cl-/I-/HCO3- exchanger playing a fundamental role in controlling blood pressure and airway function, therefore representing an attractive target for the treatment of hypertensive states and respiratory distresses. A review of the literature regarding the ability of some
Optimization of a parallel artificial membrane permeability assay for the fast and simultaneous prediction of human intestinal absorption and plasma protein binding of drug candidates: application to dibenz [b, f] azepine-5-carboxamide derivatives
Fortuna A, et al.
Journal of Pharmaceutical Sciences, 101(2), 530-540 (2012)
Julio D Duarte et al.
Expert review of cardiovascular therapy, 8(6), 793-802 (2010-06-10)
Thiazide and thiazide-like diuretics are among the most commonly used antihypertensives and have been available for over 50 years. However, the mechanism by which these drugs chronically lower blood pressure is poorly understood. Possible mechanisms include direct endothelial- or vascular
Charlotte K Leech et al.
Acta crystallographica. Section B, Structural science, 64(Pt 1), 101-107 (2008-01-22)
The compounds chlorothiazide and hydrochlorothiazide (crystalline form II) have been studied in their fully hydrogenous forms by powder neutron diffraction on the GEM diffractometer. The results of joint Rietveld refinement of the structures against multi-bank neutron and single-bank X-ray powder
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