Identification

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Name
Chlorthalidone
Accession Number
DB00310  (APRD00127)
Type
Small Molecule
Groups
Approved
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[5].

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[1]. 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 Lisinopril, Amlodipine, or Doxazosin [2, 3]. 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 Hydrochlorothiazide. 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[7].

Structure
Thumb
Synonyms
  • 1-keto-3-(3'-sulfamyl-4'-chlorophenyl)-3-hydroxyisoindoline
  • 1-oxo-3-(3-sulfamyl-4-chlorophenyl)-3-hydroxyisoindoline
  • 2-chloro-5-(1-hydroxy-3-oxo-1-isoindolinyl)benzenesulfonamide
  • 2-chloro-5-(2,3-dihydro-1-hydroxy-3-oxo-1H-isoindol-1-yl)benzenesulfonamide
  • 3-(4'-chloro-3'-sulfamoylphenyl)-3-hydroxyphthalimidine
  • 3-hydroxy-3-(4-chloro-3-sulfamylphenyl)phthalimidine
  • Chlorphthalidolone
  • Chlortalidone
  • Chlortalidonum
  • Chlorthalidone
  • Clortalidona
  • Phthalamodine
  • Phthalamudine
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Chlorthalidone Tab 100mgTablet100 mgOralApotex Corporation1976-12-31Not applicableCanada
ChlorthalidoneTablet50 mgOralAa Pharma Inc1976-12-31Not applicableCanada
Chlorthalidone 100mg TabletsTablet100 mgOralLaboratoires Confab IncNot applicableNot applicableCanada
Chlorthalidone 50mg TabletsTablet50 mgOralLaboratoires Confab IncNot applicableNot applicableCanada
Chlorthalidone Tab 100mgTablet100 mgOralDuchesnay Inc.1978-12-312003-07-18Canada
Chlorthalidone Tab 100mgTablet100 mgOralPro Doc Limitee1978-12-311999-08-12Canada
Chlorthalidone Tab 50mgTablet50 mgOralDuchesnay Inc.1978-12-312003-07-18Canada
Chlorthalidone Tab 50mgTablet50 mgOralPro Doc Limitee1978-12-311999-08-12Canada
Hygroton 50mgTablet50 mgOralNovartis1968-12-311999-08-04Canada
ThalitoneTablet15 mg/1OralMonarch Pharmaceuticals, Inc.1988-12-20Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ChlorthalidoneTablet25 mg/1OralAphena Pharma Solutions Tennessee, Inc.2016-02-12Not applicableUs
ChlorthalidoneTablet50 mg/1OralAphena Pharma Solutions Tennessee, Inc.2016-02-12Not applicableUs
ChlorthalidoneTablet25 mg/1OralAppco Pharma Llc2018-10-22Not applicableUs
ChlorthalidoneTablet50 mg/1OralAppco Pharma Llc2018-10-22Not applicableUs
ChlorthalidoneTablet50 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2017-05-17Not applicableUs
ChlorthalidoneTablet25 mg/1OralSun Pharmaceutical Industries Limited2016-02-12Not applicableUs
ChlorthalidoneTablet50 mg/1OralSun Pharmaceutical Industries Limited2016-02-12Not applicableUs
ChlorthalidoneTablet50 mg/1OralA-S Medication Solutions2016-02-12Not applicableUs
ChlorthalidoneTablet25 mg/1OralRemedy Repack2017-09-19Not applicableUs
ChlorthalidoneTablet25 mg/1OralNucare Pharmaceuticals, Inc.2016-02-12Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Apo-atenidoneChlorthalidone (25 mg) + Atenolol (50 mg)TabletOralApotex Corporation2004-08-12Not applicableCanada
Apo-atenidoneChlorthalidone (25 mg) + Atenolol (100 mg)TabletOralApotex Corporation2004-08-12Not applicableCanada
Atenolol and ChlorthalidoneChlorthalidone (25 mg/1) + Atenolol (50 mg/1)TabletOralRemedy Repack2013-02-222014-02-22Us00378 2063 01 nlmimage10 8233c15e
Atenolol and ChlorthalidoneChlorthalidone (25 mg/1) + Atenolol (100 mg/1)TabletOralLake Erie Medical Dba Quality Care Produts Llc2013-03-282015-12-31Us
Atenolol and ChlorthalidoneChlorthalidone (25 mg/1) + Atenolol (50 mg/1)TabletOralAidarex Pharmaceuticals LLC1992-08-01Not applicableUs
Atenolol and ChlorthalidoneChlorthalidone (25 mg/1) + Atenolol (100 mg/1)TabletOralbryant ranch prepack1992-08-012018-05-29Us
Atenolol and ChlorthalidoneChlorthalidone (25 mg/1) + Atenolol (50 mg/1)TabletOralMylan Pharmaceuticals Inc.1993-10-312020-04-30Us0378 206320180913 8702 rfj0yw
Atenolol and ChlorthalidoneChlorthalidone (25 mg/1) + Atenolol (100 mg/1)TabletOralMylan Pharmaceuticals Inc.1993-10-312020-04-30Us
Atenolol and ChlorthalidoneChlorthalidone (25 mg/1) + Atenolol (50 mg/1)TabletOralZydus Pharmaceuticals (USA) Inc.2019-03-12Not applicableUs
Atenolol and ChlorthalidoneChlorthalidone (25 mg/1) + Atenolol (100 mg/1)TabletOralZydus Pharmaceuticals (USA) Inc.2019-03-12Not applicableUs
International/Other Brands
Hygroton (Novartis) / Saluretin (Balkanpharma)
Categories
UNII
Q0MQD1073Q
CAS number
77-36-1
Weight
Average: 338.766
Monoisotopic: 338.012805247
Chemical Formula
C14H11ClN2O4S
InChI Key
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)
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=CC=CC=C12

Pharmacology

Indication

Chlorthalidone is indicated in the 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.

Chlorthalidone is indicated as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy.

Chlorthalidone has also been found useful in edema due to various forms of renal dysfunction, such as nephrotic syndrome, acute glomerulonephritis, and chronic renal failure.

Associated Conditions
Pharmacodynamics
Not Available
Mechanism of action

Chlorthalidone prevents reabsorption of sodium and chloride through inhibition of the Na+/Cl- symporter in the corticol diluting segment of the ascending limb of the loop of Henle[4]. Reduction of sodium reabsorption subsequently reduces extracellular fluid and plasma volume via an osmotic, sodium-driven diuresis. By increasing the delivery of sodium to the distal renal tubule, Chlorthalidone indirectly increases potassium excretion via the sodium-potassium exchange mechanism. 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 which therefore requires decreased cardiac output and overall lowers blood pressure[5]. 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[7].

TargetActionsOrganism
ASolute carrier family 12 member 1
inhibitor
Humans
ACarbonic anhydrase 1
inhibitor
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption
Not Available
Volume of distribution

Chlorthalidone has been shown to rapidly concentrate within erythrocytes and subsequently equilibrate via a slow diffusion back into the serum compartment, resulting in a large volume of distribution.[6]

Protein binding

Approximately 75 percent of the drug is bound to plasma proteins, 58 percent of the drug being bound to albumin [Label]. This is caused by an increased affinity of the drug to erythrocyte carbonic anhydrase.

Metabolism

Liver

Route of elimination

Approximately 50% of the administered dose is excreted unmetabolized through the kidney, and excretion is characterized by biphasic elimination with a rapid phase followed by a slow secretory phase[6].

Half life

40-50 hours [Label, 6].

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Chlorthalidone Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of hypotension can be increased when Chlorthalidone is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
1-benzylimidazole1-benzylimidazole may decrease the antihypertensive activities of Chlorthalidone.
1alpha-Hydroxyvitamin D5The risk or severity of hypercalcemia can be increased when Chlorthalidone is combined with 1alpha-Hydroxyvitamin D5.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Chlorthalidone.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the antihypertensive activities of Chlorthalidone.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the antihypertensive activities of Chlorthalidone.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the antihypertensive activities of Chlorthalidone.
4-Methoxyamphetamine4-Methoxyamphetamine may decrease the antihypertensive activities of Chlorthalidone.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may decrease the antihypertensive activities of Chlorthalidone.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Chlorthalidone.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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  • Evidence Level
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Food Interactions
  • Take with food (increases availability).

References

Synthesis Reference

Graf, W., Schmid, E. and Stoll, W.G.; US Patent 3,055,904; September 25,1962; assigned to Geigy Chemical Corporation.

General References
  1. Wright JM, Lee CH, Chambers GK: Systematic review of antihypertensive therapies: does the evidence assist in choosing a first-line drug? CMAJ. 1999 Jul 13;161(1):25-32. [PubMed:10420860]
  2. Siragy HM: Major outcomes in high-risk hypertensive patients randomized to angiotensin-converting enzyme inhibitors or calcium channel blocker vs diuretic. The Antihypertensive and Lipid-Lowering Treatment to Prevent Heart Attack Trial (ALLHAT). Curr Hypertens Rep. 2003 Aug;5(4):293-4. [PubMed:12844462]
  3. Authors unspecified: Major cardiovascular events in hypertensive patients randomized to doxazosin vs chlorthalidone: the antihypertensive and lipid-lowering treatment to prevent heart attack trial (ALLHAT). ALLHAT Collaborative Research Group. JAMA. 2000 Apr 19;283(15):1967-75. [PubMed:10789664]
  4. Gamba G: The thiazide-sensitive Na+-Cl- cotransporter: molecular biology, functional properties, and regulation by WNKs. Am J Physiol Renal Physiol. 2009 Oct;297(4):F838-48. doi: 10.1152/ajprenal.00159.2009. Epub 2009 May 27. [PubMed:19474192]
  5. Shahin MH, Johnson JA: Mechanisms and pharmacogenetic signals underlying thiazide diuretics blood pressure response. Curr Opin Pharmacol. 2016 Apr;27:31-7. doi: 10.1016/j.coph.2016.01.005. Epub 2016 Feb 10. [PubMed:26874237]
  6. Kountz DS, Goldman A, Mikhail J, Ezer M: Chlorthalidone: the forgotten diuretic. Postgrad Med. 2012 Jan;124(1):60-6. doi: 10.3810/pgm.2012.01.2518. [PubMed:22314115]
  7. Woodman R, Brown C, Lockette W: Chlorthalidone decreases platelet aggregation and vascular permeability and promotes angiogenesis. Hypertension. 2010 Sep;56(3):463-70. doi: 10.1161/HYPERTENSIONAHA.110.154476. Epub 2010 Jul 12. [PubMed:20625077]
External Links
Human Metabolome Database
HMDB0014455
KEGG Drug
D00272
PubChem Compound
2732
PubChem Substance
46505541
ChemSpider
2631
BindingDB
25900
ChEBI
3654
ChEMBL
CHEMBL1055
Therapeutic Targets Database
DAP000521
PharmGKB
PA448970
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Chlorthalidone
ATC Codes
G01AE10 — Combinations of sulfonamidesC03EA06 — Chlortalidone and potassium-sparing agentsC03BB04 — Chlortalidone and potassiumC03BA04 — Chlortalidone
AHFS Codes
  • 40:28.24 — Thiazide-like Diuretics
FDA label
Download (631 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHigh Blood Pressure (Hypertension)1
1CompletedBasic ScienceHigh Blood Pressure (Hypertension)1
1CompletedBasic ScienceHypertension(HTN)1
1CompletedTreatmentHigh Blood Pressure (Hypertension)1
2CompletedTreatmentCardiovascular Disease (CVD) / Heart Diseases / High Blood Pressure (Hypertension) / Vascular Diseases2
2CompletedTreatmentHigh Blood Pressure (Hypertension)1
2Not Yet RecruitingTreatmentDiabetes, Diabetes Mellitus Type 1 / Hypercalciuria1
2RecruitingTreatmentHigh Blood Pressure (Hypertension) / Renal Insufficiency,Chronic1
3CompletedNot AvailableCardiovascular Disease (CVD) / Death, Sudden,Cardiac / Heart Arrest / Heart Diseases / High Blood Pressure (Hypertension)1
3CompletedPreventionAtherosclerosis / Cardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / High Blood Pressure (Hypertension) / High Cholesterol / Type 2 Diabetes Mellitus1
3CompletedPreventionCardiovascular Disease (CVD) / Cerebrovascular Disorders / Heart Diseases / High Blood Pressure (Hypertension)1
3CompletedPreventionCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Diabetes Mellitus (DM) / Heart Diseases / Heart Failure / High Blood Pressure (Hypertension) / High Cholesterol / Myocardial Infarction / Myocardial Ischemia1
3CompletedTreatmentCardiovascular Disease (CVD) / Heart Diseases / High Blood Pressure (Hypertension)1
3CompletedTreatmentCardiovascular Disease (CVD) / Heart Diseases / High Blood Pressure (Hypertension) / Vascular Diseases1
3CompletedTreatmentHigh Blood Pressure (Hypertension)4
3CompletedTreatmentHigh Blood Pressure (Hypertension) / Obstructive Sleep Apnea (OSA)1
3CompletedTreatmentHigh Blood Pressure (Hypertension) / Transplantation, Kidney1
3CompletedTreatmentHypertension,Essential5
3CompletedTreatmentSafety1
3RecruitingTreatmentHigh Blood Pressure (Hypertension)1
3WithdrawnTreatmentEssential Arterial Hypertension2
4Active Not RecruitingTreatmentCardio-Renal Syndrome / Renal Insufficiency,Chronic1
4CompletedTreatmentChronic Kidney Disease (CKD) / Poorly-Controlled Hypertension1
4CompletedTreatmentHigh Blood Pressure (Hypertension)1
4RecruitingTreatmentAortic Valve Insufficiency / Aortic Valve Stenosis / High Blood Pressure (Hypertension) / Left Ventricular Hypertrophy / LVM1
4RecruitingTreatmentHigh Blood Pressure (Hypertension)2
4RecruitingTreatmentHypertension,Essential1
4TerminatedTreatmentDiabetes Mellitus (DM) / High Blood Pressure (Hypertension) / Stage 2 Hypertension1
4WithdrawnTreatmentHigh Blood Pressure (Hypertension)2
4WithdrawnTreatmentResistant Hypertension in Kidney Transplant Patients1
Not AvailableActive Not RecruitingTreatmentHigh Blood Pressure (Hypertension)1
Not AvailableCompletedNot AvailableCardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Heart Diseases / High Blood Pressure (Hypertension) / Myocardial Infarction1
Not AvailableCompletedNot AvailableHigh Blood Pressure (Hypertension)1
Not AvailableCompletedNot AvailableHigh Blood Pressure (Hypertension) / Hypertension,Essential / Resistant Hypertension1
Not AvailableCompletedDiagnosticHigh Blood Pressure (Hypertension)1
Not AvailableCompletedTreatmentAmbulatory Blood Pressure Monitoring / Arterial Stiffness1
Not AvailableRecruitingPreventionHigh Blood Pressure (Hypertension)1
Not AvailableRecruitingPreventionRenal Stones1

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
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Apothecon
  • A-S Medication Solutions LLC
  • AstraZeneca Inc.
  • Bryant Ranch Prepack
  • Comprehensive Consultant Services Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • H and H Laboratories
  • Hl Moore Drug Exchange
  • IPR Pharmaceuticals Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • King Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Major Pharmaceuticals
  • Medvantx Inc.
  • Merckle GmbH
  • Monarch Pharmacy
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mutual Pharmaceutical Co.
  • Mylan
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Pliva Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepak Systems Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Remedy Repack
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • Stat Scripts LLC
  • UDL Laboratories
  • Watson Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral25 mg/1
TabletOral50 mg/1
TabletOral50 mg
TabletOral
TabletOral15 mg/1
TabletOral100 mg
Prices
Unit descriptionCostUnit
Tenoretic 100 100-25 mg tablet2.91USD tablet
Tenoretic 100 tablet2.91USD tablet
Tenoretic 50 50-25 mg tablet2.18USD tablet
Tenoretic 50 tablet2.07USD tablet
Thalitone 15 mg tablet1.55USD tablet
Chlorthalidone 100 mg tablet1.07USD tablet
Chlorthalidone 50 mg tablet0.46USD tablet
Chlorthalidone 25 mg tablet0.28USD tablet
Apo-Chlorthalidone 50 mg Tablet0.13USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US9169238No2015-10-272030-02-25Us
US7572920No2009-08-112025-01-07Us
US9066936No2015-06-302028-03-26Us
US7157584No2007-01-022025-05-22Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

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Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)239 °CPhysProp
water solubility120 mg/L (at 20 °C)MERCK INDEX (1996)
logP0.85BERTHOD,A ET AL. (1999)
Predicted Properties
PropertyValueSource
Water Solubility0.0528 mg/mLALOGPS
logP1.27ALOGPS
logP1.6ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.76ChemAxon
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
Polarizability31.29 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.5447
Caco-2 permeable-0.6272
P-glycoprotein substrateNon-substrate0.767
P-glycoprotein inhibitor INon-inhibitor0.9603
P-glycoprotein inhibitor IINon-inhibitor0.9573
Renal organic cation transporterNon-inhibitor0.891
CYP450 2C9 substrateNon-substrate0.6403
CYP450 2D6 substrateNon-substrate0.822
CYP450 3A4 substrateNon-substrate0.6369
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9299
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8193
Ames testNon AMES toxic0.7277
CarcinogenicityNon-carcinogens0.5752
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.8623 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9968
hERG inhibition (predictor II)Non-inhibitor0.8914
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-0609000000-faf1d2e7aeaeb67be716
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000b-1910000000-e0b8fe4609e6388b1ffd
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-002b-4910000000-73abcbf2a1d59168b6bf
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-002b-7900000000-f7d1994811fe2a4e97a7
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004j-9600000000-fa803d15f1d75531f680
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-01ta-9300000000-f8f2617e8f0094998274
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0009000000-0395bc83917f9fc4af05
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0029000000-bbee59ce6cba3ba80a24
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-0192000000-8f7aa98268ee9e344849
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-1490000000-7e99919cc132fee88dbf
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udr-1950000000-4195d981453db67a37b0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-1910000000-27cef04d1420bbc9441e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0269000000-ea7da059eeece096f30e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-2982000000-a0107386ee7e2a9cf40e

Taxonomy

Description
This compound 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
Benzenesulfonamides / Benzenesulfonyl compounds / Isoindoles / Chlorobenzenes / Aryl chlorides / Organosulfonamides / Aminosulfonyl compounds / Lactams / Secondary carboxylic acid amides / Alkanolamines
show 6 more
Substituents
Benzenesulfonamide / Isoindolone / Isoindole / Benzenesulfonyl group / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Organosulfonic acid amide
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
sulfonamide, monochlorobenzenes, isoindoles (CHEBI:3654)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Sodium:potassium:chloride symporter activity
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
Uniprot Name
Solute carrier family 12 member 1
Molecular Weight
121449.13 Da
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]
  4. Gamba G: The thiazide-sensitive Na+-Cl- cotransporter: molecular biology, functional properties, and regulation by WNKs. Am J Physiol Renal Physiol. 2009 Oct;297(4):F838-48. doi: 10.1152/ajprenal.00159.2009. Epub 2009 May 27. [PubMed:19474192]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name
CA1
Uniprot ID
P00915
Uniprot Name
Carbonic anhydrase 1
Molecular Weight
28870.0 Da
References
  1. Woodman R, Brown C, Lockette W: Chlorthalidone decreases platelet aggregation and vascular permeability and promotes angiogenesis. Hypertension. 2010 Sep;56(3):463-70. doi: 10.1161/HYPERTENSIONAHA.110.154476. Epub 2010 Jul 12. [PubMed:20625077]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da

Drug created on June 13, 2005 07:24 / Updated on April 24, 2019 15:23