3-[(benzylsulfanyl)methyl]-6-chloro-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide

• ChemBase编号: 444
• 分子式: C15H14ClN3O4S3
• 平均质量: 431.93736
• 单一同位素质量: 430.98349662
• SMILES: Clc1c(S(=O)(=O)N)cc2S(=O)(=O)N=C(Nc2c1)CSCc1ccccc1
• Canonical SMILES: Clc1cc2NC(=NS(=O)(=O)c2cc1S(=O)(=O)N)CSCc1ccccc1
• InChI: InChI=1S/C15H14ClN3O4S3/c16-11-6-12-14(7-13(11)25(17,20)21)26(22,23)19-15(18-12)9-24-8-10-4-2-1-3-5-10/h1-7H,8-9H2,(H,18,19)(H2,17,20,21)
• InChIKey: NDTSRXAMMQDVSW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-[(benzylsulfanyl)methyl]-6-chloro-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide; 3-[(benzylsulfanyl)methyl]-6-chloro-1,1-dioxo-4H-1λ^6,2,4-benzothiadiazine-7-sulfonamide
• IUPAC传统名: regulon
• 商标名: Aquatag; Benzothiazide; Benzthazide; Dihydrex; Diucen; Edemex; Exna; Exosalt; Fovane; Freeuril; Hydrine; Lemazide; Naclex; Pfizer 1393; Proaqua; Urese
• 别名: Benzthiazide; 6-Chloro-3-[[(phenylmethyl)thio]methyl]-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-Dioxide; 3-[(Benzylthio)methyl]-6-chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-Dioxide; Aquatag; Benzothiazide; Dihydrex; Diucen; Diucene; Edemex; ExNa; Exosalt; Fovane; Freeuril; HyDrine; Lemazide; P 1393; Pfizer 1393; Proaqua; Regulon; Urese

登记号

• CAS号: 91-33-8
• PubChem SID: 160963907; 46506752
• PubChem CID: 2343
• CHEBI ID: 3047
• CHEMBL: 1201039
• Chemspider ID: 2253
• DrugBank ID: DB00562
• KEGG ID: D00651
• 美国药典/FDA物质标识码: 1TD8J48L61
• 维基百科标题: Benzthiazide

理论计算性质

JChem

• Acid pKa: 8.766833
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): 1.8404658
• LogD (pH = 7.4): 1.8236142
• Log P: 1.840787
• 摩尔折射率: 104.1407 cm^3
• 极化性: 41.080338 Å^3
• 极化表面积: 118.69 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.26
• LOG S: -4.53
• 溶解度: 1.29e-02 g/l

分子性质

理化性质

• 溶解度: 8.91 mg/L
• 疏水性(logP): 1.7

药理学性质

• 给药途径: Oral
• 生物利用度: 60 to 70%
• 排泄: Renal
• 半衰期: 5 to 15 hours
• 蛋白结合率: 30%
• 法定药品分级: Rx-only

详细说明

DrugBank - DB00562

• Drug Groups: approved
• Description: Benzthiazide is used to treat hypertension and edema. Like other thiazides, benzthiazide promotes water loss from the body (diuretics). They 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.
• Indication: For the treatment of high blood pressure and management of edema.
• Pharmacology: Benzthiazide is used to treat hypertension and edema. Like other thiazides, benzthiazide promotes water loss from the body (diuretics). They 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: Symptoms of overdose include nausea, vomiting, fatigue, urinary problems and drowsiness.
• Affected Organisms: Humans and other mammals
• Absorption: Absorbed in the digestive tract.
• Protein Binding: 30%

Toronto Research Chemicals - B209925

Benzthiazide is a diuretic, antihypertensive agent.

参考文献

• Mollica, J., et al.: J. Pharm. Sci., 58, 635 (1969)
• Chienthavorn, O., et al.: J. Pharm. Biomed. Anal., 36, 477 (1969)