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

• ChemBase ID: 117
• Molecular Formular: C9H11Cl2N3O4S2
• Molecular Mass: 360.23734
• Monoisotopic Mass: 358.95680321
• SMILES: ClCC1N(S(=O)(=O)c2c(N1)cc(Cl)c(S(=O)(=O)N)c2)C
• Canonical SMILES: ClCC1Nc2cc(Cl)c(cc2S(=O)(=O)N1C)S(=O)(=O)N
• InChI: InChI=1S/C9H11Cl2N3O4S2/c1-14-9(4-10)13-6-2-5(11)7(19(12,15)16)3-8(6)20(14,17)18/h2-3,9,13H,4H2,1H3,(H2,12,15,16)
• InChIKey: CESYKOGBSMNBPD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-3-(chloromethyl)-2-methyl-1,1-dioxo-3,4-dihydro-2H-1λ^6,2,4-benzothiadiazine-7-sulfonamide; 6-chloro-3-(chloromethyl)-2-methyl-1,1-dioxo-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide
• IUPAC Traditional name: methyclothiazide; naturon
• Brand Name: Aquaresen; Aquatensen; Duretic; Enduron; Enduronum
• Synonyms: 6-chloro-3-(chloromethyl)-2-methyl-1,1-dioxo-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide; Methychlothiazide; Methyclothiazid; Methycyclothiazide; Methylchlorothiazide; Methylclothiazide; Methylcyclothiazide; Methyclothiazide

Database IDs

• CAS Number: 135-07-9
• MDL Number: MFCD00242610
• PubChem SID: 160963580; 46509197
• PubChem CID: 4121

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.291687
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.52826226
• LogD (pH = 7.4): 0.5233532
• Log P: 0.52832526
• Molar Refractivity: 77.2777 cm^3
• Polarizability: 30.891014 Å^3
• Polar Surface Area: 109.57 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.93
• LOG S: -2.64
• Solubility (Water): 8.24e-01 g/l

PROPERTIES

Physical Property

• Solubility: 11.2 mg/L
• Hydrophobicity(logP): 0.6; 0.937

Pharmacology Properties

• Target: Others

Product Information

• Purity: 95%
• Salt Data: Free Base

DETAILS

DrugBank - DB00232

• Drug Groups: approved
• Description: A thiazide diuretic with properties similar to those of hydrochlorothiazide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p825)
• Indication: For use in the management of hypertension either as the sole therapeutic agent or to enhance the effect of other antihypertensive drugs in the more severe forms of hypertension. Also used as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy.
• Pharmacology: Methyclothiazide, a diuretic-antihypertensive agent, is a member of the benzothiadiazine (thiazide) class of drugs. Methyclothiazide has a per mg natriuretic activity approximately 100 times that of the prototype thiazide, chlorothiazide. At maximal therapeutic dosages, all thiazides are approximately equal in their diuretic/natriuretic effects. Like other benzothiadiazines, methyclothiazide also has antihypertensive properties, and may be used for this purpose either alone or to enhance the antihypertensive action of other drugs.
• Toxicity: Acute oral toxicity (LD₅₀): >4000 mg/kg [Rat]. Symptoms of overdosage include electrolyte imbalance and signs of potassium deficiency such as confusion, dizziness, muscular weakness, and gastrointestinal disturbances.
• Affected Organisms: Humans and other mammals
• Absorption: Rapidly absorbed following oral administration.
• External Links: RxList; Drugs.com