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

• ChemBase编号: 654
• 分子式: C8H8F3N3O4S2
• 平均质量: 331.2920296
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 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传统名: hydroflumethiazide
• 商标名: Diuredemina; Diurometon; Enjit; Flutizide; Glomerulin; Hidroalogen; Robezon; Spandiuril
• 别名: 氢氟噻嗪; 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

登记号

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

理论计算性质

JChem

• Acid pKa: 9.0659685
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -0.30191863
• LogD (pH = 7.4): -0.31005037
• Log P: -0.30181396
• 摩尔折射率: 64.2785 cm^3
• 极化性: 24.82975 Å^3
• 极化表面积: 118.36 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.44
• LOG S: -2.59
• 溶解度: 8.58e-01 g/l

分子性质

理化性质

• 溶解度: 0.3 mg/mL at 25 oC [MERCK INDEX (1996)]; DMSO; Methanol
• 外观: White Solid
• 熔点: 265-268°C (dec.); 272-273°C
• 疏水性(logP): -0.2

安全信息

• 保存条件: Refrigerator
• 保存注意事项: Irritant
• RTECS编号: DK9625000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 2
• 危险公开号: 42/43
• 安全公开号: 36
• GHS危险品标识: GHS08
• GHS警示词: Danger
• GHS危险声明: H317-H334
• GHS警示性声明: P261-P280-P342 + P311
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

产品相关信息

• 纯度: ~97%

详细说明

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.

参考文献

• 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)