2-chloro-5-(1-hydroxy-3-oxo-2,3-dihydro-1H-isoindol-1-yl)benzene-1-sulfonamide

• ChemBase ID: 195
• Molecular Formular: C14H11ClN2O4S
• Molecular Mass: 338.76614
• Monoisotopic Mass: 338.01280552
• SMILES: Clc1c(S(=O)(=O)N)cc(C2(O)NC(=O)c3c2cccc3)cc1
• Canonical SMILES: O=C1NC(c2c1cccc2)(O)c1ccc(c(c1)S(=O)(=O)N)Cl
• InChI: InChI=1S/C14H11ClN2O4S/c15-11-6-5-8(7-12(11)22(16,20)21)14(19)10-4-2-1-3-9(10)13(18)17-14/h1-7,19H,(H,17,18)(H2,16,20,21)
• InChIKey: JIVPVXMEBJLZRO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloro-5-(1-hydroxy-3-oxo-2,3-dihydro-1H-isoindol-1-yl)benzene-1-sulfonamide
• IUPAC Traditional name: chlorthalidone
• Brand Name: Higroton; Hydro-Long; Hygroton; Igroton; Isoren; Natriuran; Oradil; Phthalamodine; Phthalamudine; Renon; Saluretin; Tenoretic; Thalitone; Zambesil
• Synonyms: 2-Chloro-5-(2,3-dihydro-1-hydroxy-3-oxo-1H-isoindol-1-yl)-benzenesulfonamide; 3-Hydroxy-3-[4-chloro-3-sulfamylphenyl]phthalimidine; Chlorthalidone; Hygroton; Igroton; Phthalamudine; Zambesil; NSC 69200; Chlorothalidone; Chlorphthalidolone; Chlorphthalidone; Chlortalidone; Chlorthalidon; Clodronic Acid; Chlorthalidone; 2-Chloro-5-(1-hydroxy-3-oxoisoindolin-1-yl)benzenesulfonamide

Database IDs

• CAS Number: 77-36-1
• MDL Number: MFCD00036257
• PubChem SID: 46505541; 160963658
• PubChem CID: 2732

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.579576
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.6031008
• LogD (pH = 7.4): 1.5784703
• Log P: 1.6034211
• Molar Refractivity: 81.3005 cm^3
• Polarizability: 31.75829 Å^3
• Polar Surface Area: 109.49 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.27
• LOG S: -3.81
• Solubility (Water): 5.28e-02 g/l

PROPERTIES

Physical Property

• Solubility: 120 mg/L; DMSO; Methanol
• Apperance: White Solid
• Melting Point: >215°C (dec.)
• Hydrophobicity(logP): 1.3

Safety Information

• Storage Condition: -20°C Freezer

Product Information

• Purity: 95+%

DETAILS

DrugBank - DB00310

• Drug Groups: approved
• Description: A benzenesulfonamide-phthalimidine that tautomerizes to a benzophenones form. It is considered a thiazide-like diuretic. [PubChem]
• Indication: For 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.
• Pharmacology: Chlorthalidone, a monosulfonamyl diuretic, differs form other thiazide diuretics in that a double ring system is incorporated into its structure. Chlorthalidone is used alone or with atenolol in the management of hypertension and edema.
• Toxicity: Symptoms of overdose include nausea, weakness, dizziness and disturbances of electrolyte balance.
• Affected Organisms: Humans and other mammals
• Biotransformation: Liver
• Absorption: Absorbed relatively rapidly after oral administration.
• Half Life: 40 hours
• Protein Binding: High (75% [58% to albumin])
• Elimination: The major portion of the drug is excreted unchanged by the kidneys.
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - C427500

Chlorthalidone is used as a diuretic; antihypertensive.

REFERENCES

• Beisenherz, et al.: Arch. Int. Pharmacodyn. Ther., 161, 76 (1966)
• Zsoter, et al.: J. Pharmacol. Exp. Ther., 180, 723 (1966)
• Singer, J.M., et al.: Anal. Profiles Drug Subs., 14, 1 (1966)