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135-09-1 molecular structure
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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 and InChIs

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

Cite this record

CBID:654 http://www.chembase.cn/molecule-654.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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-1λ6,2,4-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
CAS Number
135-09-1
EC Number
205-173-8
MDL Number
MFCD00057316
PubChem SID
24895529
160964117
46505220
PubChem CID
3647

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.0659685  H Acceptors
H Donor LogD (pH = 5.5) -0.30191863 
LogD (pH = 7.4) -0.31005037  Log P -0.30181396 
Molar Refractivity 64.2785 cm3 Polarizability 24.82975 Å3
Polar Surface Area 118.36 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.44  LOG S -2.59 
Solubility (Water) 8.58e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
0.3 mg/mL at 25 oC [MERCK INDEX (1996)] expand Show data source
DMSO expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
Melting Point
265-268°C (dec.) expand Show data source
272-273°C expand Show data source
Hydrophobicity(logP)
-0.2 expand Show data source
Storage Condition
Refrigerator expand Show data source
Storage Warning
Irritant expand Show data source
RTECS
DK9625000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
42/43 expand Show data source
Safety Statements
36 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H317-H334 expand Show data source
GHS Precautionary statements
P261-P280-P342 + P311 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Purity
~97% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00774 external link
Item Information
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 external link
Antihypertensive; diuretic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

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