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

• ChemBase编号: 319
• 分子式: C15H14F3N3O4S2
• 平均质量: 421.4145696
• 单一同位素质量: 421.0377826
• SMILES: S1(=O)(=O)NC(Nc2c1cc(S(=O)(=O)N)c(c2)C(F)(F)F)Cc1ccccc1
• Canonical SMILES: O=S1(=O)NC(Cc2ccccc2)Nc2c1cc(c(c2)C(F)(F)F)S(=O)(=O)N
• InChI: InChI=1S/C15H14F3N3O4S2/c16-15(17,18)10-7-11-13(8-12(10)26(19,22)23)27(24,25)21-14(20-11)6-9-4-2-1-3-5-9/h1-5,7-8,14,20-21H,6H2,(H2,19,22,23)
• InChIKey: HDWIHXWEUNVBIY-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-benzyl-1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide; 3-benzyl-1,1-dioxo-6-(trifluoromethyl)-3,4-dihydro-2H-1λ^6,2,4-benzothiadiazine-7-sulfonamide
• IUPAC传统名: bendroflumethiazide
• 商标名: Aprinox; Bentride; Benuron; Benzy-Rodiuran; Benzylrodiuran; Berkozide; Bristuric; Bristuron; Centyl; Corzide; FT 8; Flumersil; Flumesil; Intolex; Livesan; Naigaril; Nateretin; Naturetin; Naturetin-2.5; Naturine; Neo-Naclex; Neo-Rontyl; Niagaril; Nikion; Orsile; Pluryl; Pluryle; Plusuril; Poliuron; Rautrax N; Rauzide; Relan Beta; Repicin; Salural; Salures; Sinesalin; Sodiuretic; Thiazidico; Urlea
• 别名: 3-苄基-6-三氟甲基-7-氨磺酰-3,4-二氢-2H-1,2,4-苯并噻二嗪-1,1-二氧化物; 苄氟噻嗪; 3-Benzyl-6-trifluoromethyl-7-sulfamoyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide; Bendroflumethiazide; Bendroflumethazide; Bendroflumethiazidum [INN-Latin]; Bendroflumetiazida [INN-Spanish]; Bendrofumethiazide; Bendrofluazide; Benzhydroflumethiazide; Benzydroflumethiazide; Benzylhydroflumethiazide; BHFT; Bendroflumethiazide; 3,4-Dihydro-3-(phenylmethyl)-6-(trifluoromethyl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-Dioxide; 3-Benzyl-3,4-dihydro-6-(trifluoromethyl)-2H-1,2,4-benzothiadia-zine-7-sulfonamide 1,1-Dioxide; Aprinox; Be 724A; (+/-)-Bendro-flumethiazide; Bristuron; Centyl; Corzide; FT 81; Flumersil; Naturine; Sinesaline; Sodiuretic; Thiazidico; Urlea; rac Bendroflumethiazide

登记号

• CAS号: 73-48-3
• EC号: 200-800-1
• MDL号: MFCD00078963
• PubChem SID: 160963782; 24891862; 46508672
• PubChem CID: 2315
• CHEBI ID: 3013
• ATC码: C03AA01
• CHEMBL: 1684
• Chemspider ID: 2225
• DrugBank ID: DB00436
• KEGG ID: D00650
• 美国药典/FDA物质标识码: 5Q52X6ICJI
• 维基百科标题: Bendroflumethiazide

理论计算性质

JChem

• Acid pKa: 9.043274
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 1.6982855
• LogD (pH = 7.4): 1.6896976
• Log P: 1.698396
• 摩尔折射率: 93.6846 cm^3
• 极化性: 35.91275 Å^3
• 极化表面积: 118.36 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.83
• LOG S: -3.29
• 溶解度: 2.14e-01 g/l

分子性质

理化性质

• 溶解度: 108 mg/L; DMSO; Methanol
• 外观: White Solid
• 熔点: 205-207°C
• 疏水性(logP): 1.7

安全信息

• 保存条件: Refrigerator
• RTECS编号: DK8225000
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 作用靶点: Others
• 给药途径: Oral
• 生物利用度: 100%
• 半衰期: 3-4 hours
• 代谢: extensive
• 蛋白结合率: 96%
• 法定药品分级: POM (UK)
• 妊娠期药物分类: Risk neonatal thrombocytopenia in 3rd trimester

产品相关信息

• 级别: analytical standard, for drug analysis
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C15H14F3N3O4S2

详细说明

DrugBank - DB00436

• Drug Groups: approved
• Description: A thiazide diuretic with actions and uses similar to those of hydrochlorothiazide. It has been used in the treatment of familial hyperkalemia, hypertension, edema, and urinary tract disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p810)
• Indication: For the treatment of high blood pressure and management of edema related to heart failure.
• Pharmacology: Bendroflumethiazide, a thiazide diuretic, removes excess water from the body by increasing how often you urinate (pass water) and also widens the blood vessels which helps to reduce blood pressure. It inhibits 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.
• Affected Organisms: Humans and other mammals
• Absorption: Absorbed relatively rapidly after oral administration
• Half Life: 8.5 hours
• Protein Binding: 96%
• External Links: Wikipedia; Drugs.com

Toronto Research Chemicals - B133500

Diuretic; antihypertensive.

参考文献

• Atkinson, A., et al.: Drug Metab. Dispos., 33, 1637 (2005)
• Ayrton, A., et al.: Xenobiotica, 38, 676 (2005)
• Diao, L., et al.: Pharm. Res., 26, 1890 (2005)