6-chloro-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide

• ChemBase编号: 758
• 分子式: C7H6ClN3O4S2
• 平均质量: 295.72324
• 单一同位素质量: 294.94882537
• SMILES: Clc1c(S(=O)(=O)N)cc2S(=O)(=O)N=CNc2c1
• Canonical SMILES: Clc1cc2NC=NS(=O)(=O)c2cc1S(=O)(=O)N
• InChI: InChI=1S/C7H6ClN3O4S2/c8-4-1-5-7(2-6(4)16(9,12)13)17(14,15)11-3-10-5/h1-3H,(H,10,11)(H2,9,12,13)
• InChIKey: JBMKAUGHUNFTOL-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 6-chloro-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide; 6-chloro-1,1-dioxo-4H-1λ^6,2,4-benzothiadiazine-7-sulfonamide
• IUPAC传统名: chlorothiazide; microzide
• 商标名: Aldoclor; Alurene; Chloriazid; Chlorosal; Chlorurit; Chlotride; Chlrosal; Clotride; Diupres; Diuresal; Diuril; Diuril Boluses; Diurilix; Diurite; Diutrid; Esidrix; Flumen; Hydro-D; Hydrodiuril; Microzide; Minzil; Neo-Dema; Oretic; Salisan; Salunil; Saluretil; Saluric; Sk-Chlorothiazide; Thiazide; Urinex; Warduzide; Yadalan; Zide
• 别名: 6-Chloro-7-sulfamyl-1,2,4-benzothiadiazine-1,1-dioxide; 6-Chloro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide; Chlotride; Diuril; Saluric; Urinex; Chlorothiazid; Chlorthiazide; Chlortiazid; Chlorothiazide

登记号

• CAS号: 58-94-6
• PubChem SID: 46507032; 160964221
• PubChem CID: 2720
• CHEBI ID: 3640
• ATC码: C03AA04
• CHEMBL: 842
• Chemspider ID: 2619
• DrugBank ID: DB00880
• KEGG ID: D00519
• 美国药典/FDA物质标识码: 77W477J15H
• 维基百科标题: Chlorothiazide
• Medline Plus: a682341

理论计算性质

JChem

• Acid pKa: 9.1031065
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): -0.44231102
• LogD (pH = 7.4): -0.44985485
• Log P: -0.4421815
• 摩尔折射率: 62.5082 cm^3
• 极化性: 24.935616 Å^3
• 极化表面积: 118.69 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.41
• LOG S: -2.87
• 溶解度: 3.98e-01 g/l

分子性质

理化性质

• 溶解度: 266 mg/L; Dimethyl Sulfoxide
• 外观: White to Off-White Solid
• 熔点: 300°C (dec.)
• 疏水性(logP): -0.5

安全信息

• 保存条件: Refrigerator

药理学性质

• 给药途径: Oral
• 排泄: Renal
• 半衰期: 45 to 120 minutes
• 代谢: Nil
• 法定药品分级: Rx-only (US)
• 妊娠期药物分类: C (US)

详细说明

DrugBank - DB00880

• Drug Groups: approved
• Description: A thiazide diuretic with actions and uses similar to those of hydrochlorothiazide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p812)
• Indication: Chlorothiazide is indicated as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy. It is also indicated in the management of hypertension either as the sole therapeutic agent or to enhance the effectiveness of other antihypertensive drugs in the more severe forms of hypertension.
• Pharmacology: Like other thiazides, chlorothiazide promotes water loss from the body (diuretics). 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. Chlorothiazide affects the distal renal tubular mechanism of electrolyte reabsorption. At maximal therapeutic dosages, all thiazides are approximately equal in their diuretic efficacy. Chlorothiazide increases excretion of sodium and chloride in approximately equivalent amounts. Natriuresis may be accompanied by some loss of potassium and bicarbonate. After oral doses, 10-15 percent of the dose is excreted unchanged in the urine. Chlorothiazide crosses the placental but not the blood-brain barrier and is excreted in breast milk.
• Toxicity: Oral, rat LD₅₀: > 10 g/kg. Signs of overdose include those caused by electrolyte depletion (hypokalemia, hypochloremia, hyponatremia) and dehydration resulting from excessive diuresis. If digitalis has also been administered hypokalemia may accentuate cardiac arrhythmias.
• Affected Organisms: Humans and other mammals
• Biotransformation: Chlorothiazide is not metabolized but is eliminated rapidly by the kidney.
• Absorption: Rapidly absorbed following oral administration.
• Half Life: 45-120 minutes
• Protein Binding: Approximately 40% bound to plasma proteins.
• Elimination: Chlorothiazide is not metabolized but is eliminated rapidly by the kidney. After oral doses, 10 to 15 percent of the dose is excreted unchanged in the urine. Chlorothiazide crosses the placental but not the blood-brain barrier and is excreted in breast milk.
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - C380000

Diuretic; antihypertensive.

参考文献

• Brittain, H.G., et al.: Anal. Profiles Drug Subs., 18, 33 (1989)
• Yoshida, F., et al.: J. Med. Chem., 43, 2575 (1989)
• Luan, F., et al.: Chem. Res. Toxicol., 18, 198 (1989)
• Si, H., et al.: Bioorg. Med. Chem., 14, 4834 (1989)