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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:42 UTC
HMDB IDHMDB0014455
Secondary Accession Numbers
  • HMDB14455
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
Data?1582753182
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
ChlortalidoneChEBI
PhthalamodineChEBI
PhthalamudineChEBI
HygrotonKegg
ThalitoneKegg
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
OxodolineHMDB
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 KeyJIVPVXMEBJLZRO-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Benzenesulfonamide
  • Isoindolone
  • Isoindole
  • Benzenesulfonyl group
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Organosulfonic acid amide
  • Benzenoid
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Azacycle
  • Alkanolamine
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organohalogen compound
  • Organic nitrogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point218 - 264 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.053 g/LNot Available
LogP1.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.053 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity81.3 m³·mol⁻¹ChemAxon
Polarizability31.23 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-1932000000-80f6e933d5d7eeee2db5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006t-5933000000-417e307059ffff5b4ad7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-0269000000-ea7da059eeece096f30eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0006-2982000000-a0107386ee7e2a9cf40eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0609000000-faf1d2e7aeaeb67be716Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000b-1910000000-e0b8fe4609e6388b1ffdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-002b-4910000000-73abcbf2a1d59168b6bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-002b-7900000000-f7d1994811fe2a4e97a7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004j-9600000000-fa803d15f1d75531f680Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-01ta-9300000000-f8f2617e8f0094998274Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0009000000-0395bc83917f9fc4af05Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0029000000-bbee59ce6cba3ba80a24Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0192000000-8f7aa98268ee9e344849Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-1490000000-7e99919cc132fee88dbfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udr-1950000000-4195d981453db67a37b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-1910000000-27cef04d1420bbc9441eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0269000000-ea7da059eeece096f30eSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-2982000000-a0107386ee7e2a9cf40eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-67b53043d132974133f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0429000000-0efa86c04b2da822a87cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-2951000000-738f0888b8209e7f8848Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-98e0e6f03d6613acf34fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1219000000-3fb4fa6225f52220443bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9200000000-832e9a5813b0e3609f12Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00310 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00310 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00310
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2631
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorthalidone
METLIN IDNot Available
PubChem Compound2732
PDB IDNot Available
ChEBI ID3654
Food Biomarker OntologyNot Available
VMH IDNot Available
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. [PubMed: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. [PubMed:17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]