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

• ChemBase ID: 1158
• Molecular Formular: C11H13ClF3N3O4S3
• Molecular Mass: 439.8818296
• Monoisotopic Mass: 438.97088125
• SMILES: Clc1cc2NC(N(S(=O)(=O)c2cc1S(=O)(=O)N)C)CSCC(F)(F)F
• Canonical SMILES: CN1C(CSCC(F)(F)F)Nc2c(S1(=O)=O)cc(c(c2)Cl)S(=O)(=O)N
• InChI: InChI=1S/C11H13ClF3N3O4S3/c1-18-10(4-23-5-11(13,14)15)17-7-2-6(12)8(24(16,19)20)3-9(7)25(18,21)22/h2-3,10,17H,4-5H2,1H3,(H2,16,19,20)
• InChIKey: CYLWJCABXYDINA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-chloro-2-methyl-1,1-dioxo-3-{[(2,2,2-trifluoroethyl)sulfanyl]methyl}-3,4-dihydro-2H-1$l^{6},2,4-benzothiadiazine-7-sulfonamide; 6-chloro-2-methyl-1,1-dioxo-3-{[(2,2,2-trifluoroethyl)sulfanyl]methyl}-3,4-dihydro-2H-1λ^6,2,4-benzothiadiazine-7-sulfonamide
• IUPAC Traditional name: renese; polythiazide
• Synonyms: Polythiazide; 6-Chloro-3,4-dihydro-2-methyl-3-[[2,2,2-trifluoroethyl)thio]methyl]-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-Dioxide; (±)-Nephril; (±)-Polythiazide; 6-Chloro-3,4-dihydro-2-methyl-7-sulfamoyl-3-(2,2,2-trifluoroethylthiomethyl)-2H-1,2,4-benzothiadiazine 1,1-Dioxide; Drenusil; NSC 108161; Nephril; P 2525; Renese

Database IDs

• CAS Number: 346-18-9
• PubChem SID: 160964621; 46508633
• PubChem CID: 4870

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.308278
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.1044953
• LogD (pH = 7.4): 1.0997803
• Log P: 1.1045558
• Molar Refractivity: 90.5208 cm^3
• Polarizability: 35.26063 Å^3
• Polar Surface Area: 109.57 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.13
• LOG S: -3.22
• Solubility (Water): 2.64e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.90 [SANGSTER (1994)]

DETAILS

DrugBank - DB01324

• Drug Groups: approved
• Description: A thiazide diuretic with actions and uses similar to those of hydrochlorothiazide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p826)
• Indication: Polythiazide is a thiazide diuretic used to decrease edema and decrease blood pressure.
• Pharmacology: As a thiazide diuretic, Polythiazide inhibits the sodium-chloride symporter which decreases solute reabsorption leading to a retention of water in the urine, as water normally follows solutes. More frequent urination is due to the increased loss of water that has not been retained from the body as a result of a concomitant relationship with sodium loss from the convoluted tubule. The short-term anti-hypertensive action is based on the fact that thiazides decrease preload, decreasing blood pressure
• Affected Organisms: Humans and other mammals
• External Links: RxList; Drugs.com

Toronto Research Chemicals - P689410

Polythiazide is a thiazide diuretic. Polythiazide is used in the treatment of hypertension as well as nephrotic syndrome, cirrhosis of the liver, and nutritional edema.

REFERENCES

• Kaur, J. et al.: J. Ind. Med. Assoc., 48, 13, (1967)
• Lund-Johansen, P.: Acta Med. Scand., 187, 509 (1967)
• O'Brien, E.T. et al.: Br. Heart J., 34, 1042 (1967)