1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide

• ChemBase ID: 654
• Molecular Formular: C8H8F3N3O4S2
• Molecular Mass: 331.2920296
• Monoisotopic Mass: 330.99083241
• SMILES: S1(=O)(=O)NCNc2c1cc(S(=O)(=O)N)c(c2)C(F)(F)F
• Canonical SMILES: FC(c1cc2NCNS(=O)(=O)c2cc1S(=O)(=O)N)(F)F
• InChI: InChI=1S/C8H8F3N3O4S2/c9-8(10,11)4-1-5-7(2-6(4)19(12,15)16)20(17,18)14-3-13-5/h1-2,13-14H,3H2,(H2,12,15,16)
• InChIKey: DMDGGSIALPNSEE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide; 1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1λ^6,2,4-benzothiadiazine-7-sulfonamide
• IUPAC Traditional name: hydroflumethiazide
• Brand Name: Diuredemina; Diurometon; Enjit; Flutizide; Glomerulin; Hidroalogen; Robezon; Spandiuril
• Synonyms: Dihydroflumethazide; Hydroflumethazide; Hydroflumethizide; Hidroflumetiazid; Trifluoromethylhydrazide; Trifluoromethylhydrothiazide; Hydroflumethiazide; Hydroflumethiazide; 3,4-Dihydro-6-(trifluoromethyl)-2H-1,2,4-benzothiadiazine-7-sulphonamide 1,1-dioxide 95+%; Hydroflumethiazide; 3,4-Dihydro-6-(trifluoromethyl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-Dioxide; Bristab; Bristurin; Dihydroflumethiazide; Diucardin; Elodrine; Finuret; Flutizide; Glomerulin; Hidroalogen; Leodrine; Saluron; Vergonil; 氢氟噻嗪

Database IDs

• CAS Number: 135-09-1
• EC Number: 205-173-8
• MDL Number: MFCD00057316
• PubChem SID: 160964117; 24895529; 46505220
• PubChem CID: 3647

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.0659685
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.30191863
• LogD (pH = 7.4): -0.31005037
• Log P: -0.30181396
• Molar Refractivity: 64.2785 cm^3
• Polarizability: 24.82975 Å^3
• Polar Surface Area: 118.36 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.44
• LOG S: -2.59
• Solubility (Water): 8.58e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.3 mg/mL at 25 oC [MERCK INDEX (1996)]; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 265-268°C (dec.); 272-273°C
• Hydrophobicity(logP): -0.2

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Irritant
• RTECS: DK9625000
• 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

Product Information

• Purity: ~97%

DETAILS

DrugBank - DB00774

• Drug Groups: approved
• Description: A thiazide diuretic with actions and uses similar to those of hydrochlorothiazide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p822)
• Indication: Used as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy. Also used in the management of hypertension either as the sole therapeutic agent or to enhance the effect of other antihypertensive drugs in the more severe forms of hypertension.
• Pharmacology: Hydroflumethiazide is an oral thiazide used to treat hypertension and edema. High blood pressure adds to the workload of the heart and arteries. If it continues for a long time, the heart and arteries may not function properly. This can damage the blood vessels of the brain, heart, and kidneys, resulting in a stroke, heart failure, or kidney failure. High blood pressure may also increase the risk of heart attacks. Like other thiazides, Hydroflumethiazide promotes water loss from the body (diuretics). Thiazides inhibit Na+/Cl- reabsorption from the distal convoluted tubules in the kidneys. Thiazides also cause loss of potassium and an increase in serum uric acid. Thiazides are often used to treat hypertension, but their hypotensive effects are not necessarily due to their diuretic activity. Thiazides have been shown to prevent hypertension-related morbidity and mortality although the mechanism is not fully understood. Thiazides cause vasodilation by activating calcium-activated potassium channels (large conductance) in vascular smooth muscles and inhibiting various carbonic anhydrases in vascular tissue.
• Toxicity: Overdoses lead to diuresis, lethargy progressing to coma, with minimal cardiorespiratory depression and with or without significant serum electrolyte changes or dehydration.
• Affected Organisms: Humans and other mammals
• Biotransformation: Essentially unchanged
• Absorption: Hydroflumethiazide is incompletely but fairly rapidly absorbed from the gastrointestinal tract
• Half Life: It appears to have a biphasic biological half-life with an estimated alpha-phase of about 2 hours and an estimated beta-phase of about 17 hours
• Protein Binding: 74%
• References: Moser M, Feig PU: Fifty years of thiazide diuretic therapy for hypertension. Arch Intern Med. 2009 Nov 9;169(20):1851-6. [Pubmed]
• External Links: RxList

Toronto Research Chemicals - H714630

Antihypertensive; diuretic.

REFERENCES

• Moser M, Feig PU: Fifty years of thiazide diuretic therapy for hypertension. Arch Intern Med. 2009 Nov 9;169(20):1851-6. Pubmed
• Piala, J.J., et al.: J. Pharmacol. Exp. Ther., 134, 273 (1961)
• Orzech, C.E., et al.: Anal. Profiles Drug Subs., 7, 297 (1961)