6-chloro-1,1-dioxo-2H-1λ6,2,4-benzothiadiazine-7-sulfonamide

• ChemBase ID: 72774
• Molecular Formular: C7H6ClN3O4S2
• Molecular Mass: 295.72324
• Monoisotopic Mass: 294.94882537
• SMILES: c1(c(cc2c(c1)N=CNS2(=O)=O)S(=O)(=O)N)Cl
• Canonical SMILES: Clc1cc2N=CNS(=O)(=O)c2cc1S(=O)(=O)N
• InChI: 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)
• InChIKey: JBMKAUGHUNFTOL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-1,1-dioxo-2H-1λ^6,2,4-benzothiadiazine-7-sulfonamide; 6-chloro-1,1-dioxo-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide
• IUPAC Traditional name: flumen
• Synonyms: 6-Chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide; Chlorothiazide; Diuril; Chlotride; Chlorothiazide

Database IDs

• CAS Number: 58-94-6
• EC Number: 200-404-9
• MDL Number: MFCD00058576
• PubChem SID: 162037695; 24278150
• PubChem CID: 2720

CALCULATED PROPERTIES

• Acid pKa: 6.4873347
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.34729496
• LogD (pH = 7.4): -0.9954968
• Log P: -0.30979228
• Molar Refractivity: 62.9416 cm^3
• Polarizability: 24.922909 Å^3
• Polar Surface Area: 118.69 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO

Safety Information

• Storage Condition: -20°C
• RTECS: DK9450000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 42/43
• Safety Statements: 36
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CA1(759), CA4(762), SLC12A3(6559)

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1641

Research Area: Cardiovascular disease
Biological Activity:
Chlorothiazide is a diuretic and antihypertensive. By increasing the amount of salt and water that the kidneys remove from the blood, the diuretic can lower blood pressure and help with water retention. [1] The corresponding IC50 values for the thiazide diuretics chlorothiazide, cyclothiazide, hydrochlorothiazide,and trichlormethiazide were 3.8, 84.3, 67.3 and 19.2 mM) respectively. [2]

Sigma Aldrich - C4911

Application
One of the first in the thiazide class of diuretics. The effect is sparing of calcium1 and lithium2, but increases the excretion of sodium.1

REFERENCES

• Rizwan AN et al. Pharm Res. 2007 Mar;24(3):450-70.