ContaminantDB: Chlorthalidone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:38:52 UTC

Update Date

2016-11-09 01:15:26 UTC

Accession Number

CHEM016629

Identification

Common Name

Chlorthalidone

Class

Small Molecule

Description

Chlorthalidone is a thiazide-like diuretic used for the treatment of hypertension and for management of edema caused by conditions such as heart failure or renal impairment. Chlorthalidone improves blood pressure and swelling by preventing water absorption from the kidneys through inhibition of the Na+/Cl− symporter in the distal convoluted tubule cells in the kidney. The exact mechanism of chlorthalidone's anti-hypertensive effect is under debate, however, it is thought that increased diuresis results in decreased plasma and extracellular fluid volume, decreased cardiac output and therefore overall reduction in blood pressure. Chlorthalidone is considered first-line therapy for management of uncomplicated hypertension as there is strong evidence from meta-analyses that thiazide diuretics such as chlorthalidone reduce the risk of stroke, myocardial infarction, heart failure, and cardiovascular all-cause mortality in patients with hypertension. In particular, the ALLHAT trial confirmed the role of thiazide diuretics as first-line therapy and demonstrated that chlorthalidone had a statistically significant lower incidence of stroke and heart failure when compared to , , or . Further studies have indicated that low-dose thiazides are as good as, and in some secondary endpoints, better than β-blockers, ACE inhibitors, Calcium Channel Blockers or ARBs. Chlorthalidone has been shown to have a number of pleiotropic effects that differentiate it from other diuretics such as . In addition to its antihypertensive effects, chlorthalidone has also been shown to decrease platelet aggregation and vascular permeability, as well as promote angiogenesis in vitro, which is thought to be partly the result of reductions in carbonic anhydrase–dependent pathways. These pathways may play a role in chlorthalidone's cardiovascular risk reduction effects.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Keto-3-(3'-sulfamyl-4'-chlorophenyl)-3-hydroxyisoindoline	ChEBI
1-oxo-3-(3-Sulfamyl-4-chlorophenyl)-3-hydroxyisoindoline	ChEBI
2-Chloro-5-(1-hydroxy-3-oxo-1-isoindolinyl)benzenesulfonamide	ChEBI
2-Chloro-5-(2,3-dihydro-1-hydroxy-3-oxo-1H-isoindol-1-yl)benzenesulfonamide	ChEBI
3-(4'-Chloro-3'-sulfamoylphenyl)-3-hydroxyphthalimidine	ChEBI
3-Hydroxy-3-(4-chloro-3-sulfamylphenyl)phthalimidine	ChEBI
Chlorphthalidolone	ChEBI
Chlortalidone	ChEBI
Phthalamodine	ChEBI
Phthalamudine	ChEBI
Hygroton	Kegg
Thalitone	Kegg
1-Keto-3-(3'-sulphamyl-4'-chlorophenyl)-3-hydroxyisoindoline	Generator
1-oxo-3-(3-Sulphamyl-4-chlorophenyl)-3-hydroxyisoindoline	Generator
2-Chloro-5-(1-hydroxy-3-oxo-1-isoindolinyl)benzenesulphonamide	Generator
2-Chloro-5-(2,3-dihydro-1-hydroxy-3-oxo-1H-isoindol-1-yl)benzenesulphonamide	Generator
3-(4'-Chloro-3'-sulphamoylphenyl)-3-hydroxyphthalimidine	Generator
3-Hydroxy-3-(4-chloro-3-sulphamylphenyl)phthalimidine	Generator
Chlorothalidone	HMDB
Chlorphthalidone	HMDB
Chlorthalidon	HMDB
Oxodoline	HMDB

Chemical Formula

C₁₄H₁₁ClN₂O₄S

Average Molecular Mass

338.766 g/mol

Monoisotopic Mass

338.013 g/mol

CAS Registry Number

77-36-1

IUPAC Name

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

Traditional Name

chlorthalidone

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 Key

JIVPVXMEBJLZRO-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

sulfonamide (CHEBI:3654 )
monochlorobenzenes (CHEBI:3654 )
isoindoles (CHEBI:3654 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.053 g/L	ALOGPS
logP	1.27	ALOGPS
logP	1.6	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.58	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	109.49 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.3 m³·mol⁻¹	ChemAxon
Polarizability	31.23 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-1932000000-80f6e933d5d7eeee2db5	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006t-5933000000-417e307059ffff5b4ad7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00di-0269000000-ea7da059eeece096f30e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0006-2982000000-a0107386ee7e2a9cf40e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-0609000000-faf1d2e7aeaeb67be716	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000b-1910000000-e0b8fe4609e6388b1ffd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-002b-4910000000-73abcbf2a1d59168b6bf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-002b-7900000000-f7d1994811fe2a4e97a7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004j-9600000000-fa803d15f1d75531f680	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-01ta-9300000000-f8f2617e8f0094998274	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-0009000000-0395bc83917f9fc4af05	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-00di-0029000000-bbee59ce6cba3ba80a24	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0006-0192000000-8f7aa98268ee9e344849	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0006-1490000000-7e99919cc132fee88dbf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udr-1950000000-4195d981453db67a37b0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-1910000000-27cef04d1420bbc9441e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-0269000000-ea7da059eeece096f30e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0006-2982000000-a0107386ee7e2a9cf40e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-00di-0009000000-3ff5bc6538f1dfa17848	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-0019000000-c6b20cb28198f7ab7528	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0006-1490000000-7526156fee26c5ee4f45	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-67b53043d132974133f9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0429000000-0efa86c04b2da822a87c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-2951000000-738f0888b8209e7f8848	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-98e0e6f03d6613acf34f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1219000000-3fb4fa6225f52220443b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-9200000000-832e9a5813b0e3609f12	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00310

HMDB ID

HMDB0014455

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Chlorthalidone (CHEM016629)

Structure for CHEM016629: Chlorthalidone