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

• ChemBase ID: 444
• Molecular Formular: C15H14ClN3O4S3
• Molecular Mass: 431.93736
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: regulon
• Brand Name: Aquatag; Benzothiazide; Benzthazide; Dihydrex; Diucen; Edemex; Exna; Exosalt; Fovane; Freeuril; Hydrine; Lemazide; Naclex; Pfizer 1393; Proaqua; Urese
• Synonyms: 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

Database IDs

• CAS Number: 91-33-8
• PubChem SID: 160963907; 46506752
• PubChem CID: 2343
• CHEBI ID: 3047
• CHEMBL: 1201039
• Chemspider ID: 2253
• DrugBank ID: DB00562
• KEGG ID: D00651
• Unique Ingredient Identifier: 1TD8J48L61
• Wikipedia Title: Benzthiazide

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.766833
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.8404658
• LogD (pH = 7.4): 1.8236142
• Log P: 1.840787
• Molar Refractivity: 104.1407 cm^3
• Polarizability: 41.080338 Å^3
• Polar Surface Area: 118.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.26
• LOG S: -4.53
• Solubility (Water): 1.29e-02 g/l

PROPERTIES

Physical Property

• Solubility: 8.91 mg/L
• Hydrophobicity(logP): 1.7

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 60 to 70%
• Excretion: Renal
• Half Life: 5 to 15 hours
• Protein Bound: 30%
• Legal Status: Rx-only

DETAILS

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.

REFERENCES

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