You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:28:36 UTC
HMDB IDHMDB14455
Secondary Accession NumbersNone
Metabolite Identification
Common NameChlorthalidone
DescriptionChlorthalidone is only found in individuals that have used or taken this drug. It is a benzenesulfonamide-phthalimidine that tautomerizes to a benzophenones form. It is considered a thiazide-like diuretic. [PubChem]Chlorthalidone inhibits sodium ion transport across the renal tubular epithelium in the cortical diluting segment of the ascending limb of the loop of Henle. By increasing the delivery of sodium to the distal renal tubule, Chlorthalidone indirectly increases potassium excretion via the sodium-potassium exchange mechanism.
Structure
Thumb
Synonyms
ValueSource
1-keto-3-(3'-Sulfamyl-4'-chlorophenyl)-3-hydroxyisoindolineChEBI
1-oxo-3-(3-Sulfamyl-4-chlorophenyl)-3-hydroxyisoindolineChEBI
2-chloro-5-(1-Hydroxy-3-oxo-1-isoindolinyl)benzenesulfonamideChEBI
2-chloro-5-(2,3-dihydro-1-Hydroxy-3-oxo-1H-isoindol-1-yl)benzenesulfonamideChEBI
3-(4'-chloro-3'-Sulfamoylphenyl)-3-hydroxyphthalimidineChEBI
3-Hydroxy-3-(4-chloro-3-sulfamylphenyl)phthalimidineChEBI
ChlorphthalidoloneChEBI
PhthalamodineChEBI
PhthalamudineChEBI
1-keto-3-(3'-Sulphamyl-4'-chlorophenyl)-3-hydroxyisoindolineGenerator
1-oxo-3-(3-Sulphamyl-4-chlorophenyl)-3-hydroxyisoindolineGenerator
2-chloro-5-(1-Hydroxy-3-oxo-1-isoindolinyl)benzenesulphonamideGenerator
2-chloro-5-(2,3-dihydro-1-Hydroxy-3-oxo-1H-isoindol-1-yl)benzenesulphonamideGenerator
3-(4'-chloro-3'-Sulphamoylphenyl)-3-hydroxyphthalimidineGenerator
3-Hydroxy-3-(4-chloro-3-sulphamylphenyl)phthalimidineGenerator
ChlorothalidoneHMDB
ChlorphthalidoneHMDB
ChlorthalidonHMDB
Chemical FormulaC14H11ClN2O4S
Average Molecular Weight338.766
Monoisotopic Molecular Weight338.012805247
IUPAC Name2-chloro-5-(1-hydroxy-3-oxo-2,3-dihydro-1H-isoindol-1-yl)benzene-1-sulfonamide
Traditional Namechlorthalidone
CAS Registry Number77-36-1
SMILES
NS(=O)(=O)C1=C(Cl)C=CC(=C1)C1(O)NC(=O)C2=CC=CC=C12
InChI Identifier
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)
InChI KeyInChIKey=JIVPVXMEBJLZRO-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoindoles and derivatives
Sub ClassIsoindolines
Direct ParentIsoindolones
Alternative Parents
Substituents
  • Isoindolone
  • Benzenesulfonamide
  • Isoindole
  • Halobenzene
  • Chlorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Alkanolamine
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antihypertensive Agents
  • Diuretics
  • Sodium Chloride Symporter Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point218 - 264 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.28e-02 g/LNot Available
LogP1.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.053 mg/mLALOGPS
logP1.27ALOGPS
logP1.6ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.58ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.49 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity81.3 m3·mol-1ChemAxon
Polarizability31.23 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Chlorthalidone PathwaySMP00122Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00310
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00310
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00310
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2631
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorthalidone
NuGOwiki LinkHMDB14455
Metagene LinkHMDB14455
METLIN IDNot Available
PubChem Compound2732
PDB IDNot Available
ChEBI ID3654
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Transporters

General function:
Involved in transport
Specific function:
Electrically silent transporter system. Mediates sodium and chloride reabsorption. Plays a vital role in the regulation of ionic balance and cell volume
Gene Name:
SLC12A1
Uniprot ID:
Q13621
Molecular weight:
121449.1
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]