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

• ChemBase ID: 319
• Molecular Formular: C15H14F3N3O4S2
• Molecular Mass: 421.4145696
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: bendroflumethiazide
• Brand Name: 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
• Synonyms: 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; 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

Database IDs

• CAS Number: 73-48-3
• EC Number: 200-800-1
• MDL Number: MFCD00078963
• PubChem SID: 46508672; 24891862; 160963782
• PubChem CID: 2315
• CHEBI ID: 3013
• ATC CODE: C03AA01
• CHEMBL: 1684
• Chemspider ID: 2225
• DrugBank ID: DB00436
• KEGG ID: D00650
• Unique Ingredient Identifier: 5Q52X6ICJI
• Wikipedia Title: Bendroflumethiazide

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.043274
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.6982855
• LogD (pH = 7.4): 1.6896976
• Log P: 1.698396
• Molar Refractivity: 93.6846 cm^3
• Polarizability: 35.91275 Å^3
• Polar Surface Area: 118.36 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.83
• LOG S: -3.29
• Solubility (Water): 2.14e-01 g/l

PROPERTIES

Physical Property

• Solubility: 108 mg/L; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 205-207°C
• Hydrophobicity(logP): 1.7

Safety Information

• Storage Condition: Refrigerator
• RTECS: DK8225000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: Others
• Admin Routes: Oral
• Bioavailability: 100%
• Half Life: 3-4 hours
• Metabolism: extensive
• Protein Bound: 96%
• Legal Status: POM (UK)
• Pregnancy Category: Risk neonatal thrombocytopenia in 3rd trimester

Product Information

• Grade: analytical standard, for drug analysis
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C15H14F3N3O4S2

DETAILS

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.

REFERENCES

• 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)