6-chloro-3-(dichloromethyl)-1,1-dioxo-3,4-dihydro-2H-1λ6,2,4-benzothiadiazine-7-sulfonamide

• ChemBase ID: 894
• Molecular Formular: C8H8Cl3N3O4S2
• Molecular Mass: 380.65582
• Monoisotopic Mass: 378.90218079
• SMILES: ClC(Cl)C1NS(=O)(=O)c2c(N1)cc(Cl)c(S(=O)(=O)N)c2
• Canonical SMILES: ClC(C1Nc2cc(Cl)c(cc2S(=O)(=O)N1)S(=O)(=O)N)Cl
• InChI: InChI=1S/C8H8Cl3N3O4S2/c9-3-1-4-6(2-5(3)19(12,15)16)20(17,18)14-8(13-4)7(10)11/h1-2,7-8,13-14H,(H2,12,15,16)
• InChIKey: LMJSLTNSBFUCMU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-3-(dichloromethyl)-1,1-dioxo-3,4-dihydro-2H-1λ^6,2,4-benzothiadiazine-7-sulfonamide; 6-chloro-3-(dichloromethyl)-1,1-dioxo-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide
• IUPAC Traditional name: trichlormethiazide; aquazide
• Brand Name: Achletin; Anatran; Anistadin; Aponorin; Carvacron; Chlopolidine; Cretonin; Diu-Hydrin; Diurazida; Diurese; Diuroral; Esmarin; Eurinol; Fluitran; Flurese; Flutra; Gangesol; Hydrotrichlorothiazide; Intromene; Isestran; Kubacron; Metahydrin; Metatensin; Nakva; Naqua; Naquasone; Salurin; Schebitran; Tachionin; Tolcasone; Trichlorex; Trichlormas; Trichlormetazid; Trichlormethiazid; Trichlormethiazide W/ Reserpine; Trichloromethiadiazide; Trichloromethiazide; Triclordiuride; Triclormetiazide; Triflumen
• Synonyms: Trichlormethiazide; Trichlormethiazide; 6-Chloro-3-[dichloromethyl]-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide-1,1-dioxide; TRICHLOROMETHIAZIDE; Achletin; Diu-Hydrin; Triflumen; Trichlormethiazide (Achletin)

Database IDs

• CAS Number: 133-67-5
• EC Number: 205-118-8
• MDL Number: MFCD00057315
• PubChem SID: 46508880; 24899924; 160964357
• PubChem CID: 5560

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.32218
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.97276896
• LogD (pH = 7.4): 0.9297084
• Log P: 0.97334945
• Molar Refractivity: 77.4351 cm^3
• Polarizability: 31.037252 Å^3
• Polar Surface Area: 118.36 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.86
• LOG S: -2.96
• Solubility (Water): 4.15e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.8 mg/mL at 25 oC [MERCK (1989)]
• Melting Point: 273-276°C
• Hydrophobicity(logP): 0.7

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: DK8925000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 42/43
• Safety Statements: 36
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Target: Others

Product Information

• Salt Data: Free Base

DETAILS

MP Biomedicals - 02190020

White crystalline powder

DrugBank - DB01021

• Drug Groups: approved
• Description: A thiazide diuretic with properties similar to those of hydrochlorothiazide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p830)
• Indication: Used in the treatment of oedema (including that associated with heart failure) and hypertension.
• Pharmacology: Trichloromethiazide is indicated as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy. Trichloromethiazide has also been found useful in edema due to various forms of renal dysfunction such as nephrotic syndrome, acute glomer-ulonephritis, and chronic renal failure. Trichloromethiazide 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. Like other thiazides, Trichloromethiazide 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: Oral Rat LD₅₀ = 5600 mg/kg, oral Mouse LD₅₀ = 2600 mg/kg
• Affected Organisms: Humans and other mammals

Sigma Aldrich - T1016

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. T1016.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.