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Identification
Name Chlorthalidone
Accession Number DB00310 (APRD00127)
Type small molecule
Groups approved
Description

A benzenesulfonamide-phthalimidine that tautomerizes to a benzophenones form. It is considered a thiazide-like diuretic. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Chlorothalidone
  • Chlorphthalidolone
  • Chlorphthalidone
  • Chlortalidone
  • Chlorthalidon
  • Clodronic Acid
Brand names
  • Higroton
  • Hydro-Long
  • Hygroton
  • Igroton
  • Isoren
  • Natriuran
  • Oradil
  • Phthalamodine
  • Phthalamudine
  • Renon
  • Saluretin
  • Tenoretic
  • Thalitone
  • Zambesil
Brand name mixtures
  • Tenoretic (chlorthalidone + atenolol)
Categories
  • Antihypertensive Agents
  • Diuretics
  • Sodium Chloride Symporter Inhibitors
CAS number 77-36-1
Weight Average: 338.766
Monoisotopic: 338.012805247
Chemical Formula C14H11ClN2O4S
InChI Key InChIKey=JIVPVXMEBJLZRO-UHFFFAOYSA-N
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)
Plain Text
IUPAC Name
2-chloro-5-(1-hydroxy-3-oxo-2,3-dihydro-1H-isoindol-1-yl)benzene-1-sulfonamide
SMILES
NS(=O)(=O)C1=C(Cl)C=CC(=C1)C1(O)NC(=O)C2=C1C=CC=C2
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzenesulfonamides
  • Indoles and Indole Derivatives
  • Lactams
  • Benzamides
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Amino Ketones
  • Sulfonyls
  • Benzene and Derivatives
  • Aminals and Derivatives
  • Aryl Halides
  • Carboxylic Acids and Derivatives
  • Benzenesulfonamides
  • Halobenzenes
  • Indoles and Indole Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Sulfonamides
  • Lactams
  • Benzoyl Derivatives
  • Benzamides
  • Pyrrolines
Pharmacology
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.
Pharmacodynamics 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.
Mechanism of action 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.
Absorption Absorbed relatively rapidly after oral administration.
Volume of distribution Not Available
Protein binding High (75% [58% to albumin])
Metabolism

Liver
Route of elimination The major portion of the drug is excreted unchanged by the kidneys.
Half life 40 hours
Clearance Not Available
Toxicity Symptoms of overdose include nausea, weakness, dizziness and disturbances of electrolyte balance.
Affected organisms
  • Humans and other mammals
Pathways
Pathway Name SMPDB ID
Smp00122 Chlorthalidone Pathway SMP00122
Pharmacoeconomics
Manufacturers
  • Abbott laboratories pharmaceutical products div
  • Ascot hosp pharmaceuticals inc div travenol laboratories inc
  • Clonmel healthcare ltd
  • Ivax pharmaceuticals inc
  • Kv pharmaceutical co
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Pioneer pharmaceuticals inc
  • Pliva inc
  • Purepac pharmaceutical co
  • Sandoz inc
  • Superpharm corp
  • Teva pharmaceuticals usa inc
  • Usl pharma inc
  • Vangard laboratories inc div midway medical co
  • Warner chilcott div warner lambert co
  • Watson laboratories inc
  • Sanofi aventis us llc
  • Monarch pharmaceuticals inc
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Tenoretic 100 100-25 mg tablet 2.91 USD tablet
Tenoretic 100 tablet 2.91 USD tablet
Tenoretic 50 50-25 mg tablet 2.18 USD tablet
Tenoretic 50 tablet 2.07 USD tablet
Thalitone 15 mg tablet 1.55 USD tablet
Chlorthalidone 100 mg tablet 1.07 USD tablet
Chlorthalidone 50 mg tablet 0.46 USD tablet
Chlorthalidone 25 mg tablet 0.28 USD tablet
Apo-Chlorthalidone 50 mg Tablet 0.13 USD tablet
Patents Not Available
Properties
State solid
Melting point 218-264oC
Experimental Properties
Property Value Source
water solubility 120 mg/L PhysProp
logP 1.3 PhysProp
Predicted Properties
Property Value Source
water solubility 5.28e-02 g/l ALOGPS
logP 1.27 ALOGPS
logP 1.60 ChemAxon Molconvert
logS -3.81 ALOGPS
pKa 9.22 ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 3 ChemAxon Molconvert
polar surface area 109.49 ChemAxon Molconvert
rotatable bond count 2 ChemAxon Molconvert
refractivity 81.30 ChemAxon Molconvert
polarizability 31.23 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00272 Link_out
PubChem Compound 2732 Link_out
PubChem Substance 46505541 Link_out
ChemSpider 2631 Link_out
BindingDB 25900 Link_out
ChEBI 3654 Link_out
ChEMBL 3654 Link_out
Therapeutic Targets Database DAP000521 Link_out
Drug Product Database 360279 Link_out
RxList http://www.rxlist.com/cgi/generic3/chlorthalidone.htm Link_out
Drugs.com http://www.drugs.com/cdi/chlorthalidone.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Chlorthalidone Link_out
ATC Codes
  • C03BA04
AHFS Codes
  • 40:28.24
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Take with food (increases availability).
Targets

1. Solute carrier family 12 member 1

Pharmacological action: yes
Actions: inhibitor

Electrically silent transporter system. Mediates sodium and chloride reabsorption. Plays a vital role in the regulation of ionic balance and cell volume

Organism class: human
UniProt ID: Q13621 Link_out
Gene: SLC12A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:38

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.