chlortalidone Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
625 77-36-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • clortalidone
  • phthalamudine
  • chlorphthalidolone
  • chlorthalidone
  • chlorthalidon
  • chlortalidone
A benzenesulfonamide-phthalimidine that tautomerizes to a BENZOPHENONES form. It is considered a thiazide-like diuretic.
  • Molecular weight: 338.76
  • Formula: C14H11ClN2O4S
  • CLOGP: 0.45
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 3
  • TPSA: 109.49
  • ALOGS: -3.81
  • ROTB: 2

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
25 mg O
25 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 4 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.27 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 65 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 2.46 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 3.90 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.50 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.24 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 36 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
April 7, 1960 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hyponatraemia 130.52 46.96 31 203 13294 2344557
Hypokalaemia 94.71 46.96 23 211 10631 2347220
Completed suicide 65.97 46.96 20 214 21014 2336837
Hypotension 65.35 46.96 22 212 32414 2325437
Renal failure 56.47 46.96 17 217 17332 2340519
Acute respiratory distress syndrome 49.78 46.96 11 223 3281 2354570
Inappropriate antidiuretic hormone secretion 47.82 46.96 10 224 2299 2355552

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Hyponatraemia 132.16 44.33 32 203 8968 1737578
Hypokalaemia 115.90 44.33 27 208 6347 1740199
Completed suicide 77.70 44.33 24 211 16288 1730258
Hypotension 49.31 44.33 20 215 29634 1716912

Pharmacologic Action:

SourceCodeDescription
ATC C03BA04 CARDIOVASCULAR SYSTEM
DIURETICS
LOW-CEILING DIURETICS, EXCL. THIAZIDES
Sulfonamides, plain
ATC C03BB04 CARDIOVASCULAR SYSTEM
DIURETICS
LOW-CEILING DIURETICS, EXCL. THIAZIDES
Sulfonamides and potassium in combination
ATC C03EA06 CARDIOVASCULAR SYSTEM
DIURETICS
DIURETICS AND POTASSIUM-SPARING AGENTS IN COMBINATION
Low-ceiling diuretics and potassium-sparing agents
FDA PE N0000175359 Increased Diuresis
FDA EPC N0000175420 Thiazide-like Diuretic
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D004232 Diuretics
MeSH PA D049990 Membrane Transport Modulators
MeSH PA D045283 Natriuretic Agents
MeSH PA D049993 Sodium Chloride Symporter Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Edema indication 267038008
Pulmonary Edema due to Chronic Heart Failure indication
Peripheral Edema due to Chronic Heart Failure indication
Diabetes insipidus off-label use 15771004 DOID:9409
Calcium renal calculus off-label use 427649000
Anuria contraindication 2472002 DOID:2983
Suicidal thoughts contraindication 6471006
Psoriasis contraindication 9014002 DOID:8893
Peptic ulcer contraindication 13200003 DOID:750
Hypercholesterolemia contraindication 13644009
Chronic disease of respiratory system contraindication 17097001
Myocardial infarction contraindication 22298006 DOID:5844
Electroconvulsive therapy contraindication 23835007
Complete atrioventricular block contraindication 27885002
Depressive disorder contraindication 35489007
Hyperuricemia contraindication 35885006 DOID:1920
Anaphylaxis contraindication 39579001
Hypokalemia contraindication 43339004
Diabetes mellitus type 2 contraindication 44054006 DOID:9352
Conduction disorder of the heart contraindication 44808001
Tear film insufficiency contraindication 46152009
End stage renal disease contraindication 46177005 DOID:784
Diabetes mellitus type 1 contraindication 46635009 DOID:9744
Chronic heart failure contraindication 48447003
Sinus bradycardia contraindication 49710005
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Sympathectomy contraindication 57071006
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Cerebrovascular disease contraindication 62914000 DOID:6713
Ulcerative colitis contraindication 64766004 DOID:8577
Hypercalcemia contraindication 66931009 DOID:12678
Hypochloremic alkalosis contraindication 70134007
Oliguria contraindication 83128009
Epilepsy contraindication 84757009 DOID:1826
Cardiogenic shock contraindication 89138009
Hyponatremia contraindication 89627008
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Liver function tests abnormal contraindication 166603001
Hypomagnesemia contraindication 190855004
Asthma contraindication 195967001 DOID:2841
Acute pancreatitis contraindication 197456007 DOID:2913
Atrioventricular block contraindication 233917008 DOID:0050820
Raynaud's phenomenon contraindication 266261006
Calculus in biliary tract contraindication 266474003
Pregnancy, function contraindication 289908002
Severe chronic obstructive pulmonary disease contraindication 313299006
Surgical procedure contraindication 387713003
Chronic myocardial ischemia contraindication 413844008 DOID:3393
First Degree Atrioventricular Heart Block contraindication
Acutely Decompensated HF Requiring Parenteral Inotropic Therapy contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.63 acidic
pKa2 9.38 acidic
pKa3 13.47 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
12.5MG EDARBYCLOR ARBOR PHARMS LLC N202331 Dec. 20, 2011 RX TABLET ORAL 7572920 Jan. 7, 2025 TREATMENT OF HYPERTENSION
25MG EDARBYCLOR ARBOR PHARMS LLC N202331 Dec. 20, 2011 RX TABLET ORAL 7572920 Jan. 7, 2025 TREATMENT OF HYPERTENSION
12.5MG EDARBYCLOR ARBOR PHARMS LLC N202331 Dec. 20, 2011 RX TABLET ORAL 9387249 July 1, 2031 TREATMENT OF HYPERTENSION
25MG EDARBYCLOR ARBOR PHARMS LLC N202331 Dec. 20, 2011 RX TABLET ORAL 9387249 July 1, 2031 TREATMENT OF HYPERTENSION

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Solute carrier family 12 member 3 Transporter INHIBITOR CHEMBL CHEMBL
Carbonic anhydrase 12 Enzyme Ki 8.35 CHEMBL
Carbonic anhydrase 4 Enzyme Ki 6.71 CHEMBL
Carbonic anhydrase 3 Enzyme Ki 4.96 CHEMBL
Carbonic anhydrase 5A, mitochondrial Enzyme Ki 6.04 CHEMBL
Carbonic anhydrase 2 Enzyme Kd 5.56 WOMBAT-PK
Carbonic anhydrase 7 Enzyme Ki 8.55 CHEMBL
Carbonic anhydrase 9 Enzyme Ki 7.64 CHEMBL
Carbonic anhydrase 1 Enzyme Ki 6.46 CHEMBL
Carbonic anhydrase 5B, mitochondrial Enzyme Ki 8.05 CHEMBL
Carbonic anhydrase 6 Enzyme Ki 5.87 CHEMBL
Carbonic anhydrase 14 Enzyme Ki 5.38 CHEMBL
Carbonic anhydrase 13 Enzyme Ki 7.82 CHEMBL

External reference:

IDSource
D002752 MESH_DESCRIPTOR_UI
4017887 VUID
N0000146240 NUI
C0008294 UMLSCUI
D00272 KEGG_DRUG
387324004 SNOMEDCT_US
57893000 SNOMEDCT_US
4017887 VANDF
002309 NDDF
4364 MMSL
2409 RXNORM
4432 MMSL
d00192 MMSL
CHEMBL1055 ChEMBL_ID
CHEMBL255014 ChEMBL_ID
DB00310 DRUGBANK_ID
Q0MQD1073Q UNII
1125 INN_ID
KLT PDB_CHEM_ID
CHEBI:3654 CHEBI
7147 IUPHAR_LIGAND_ID
2732 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 0378-0213 TABLET 50 mg ORAL ANDA 12 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 0378-0222 TABLET 25 mg ORAL ANDA 12 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 0591-5782 TABLET 25 mg ORAL ANDA 12 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 0591-5783 TABLET 25 mg ORAL ANDA 12 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 0904-6900 TABLET 25 mg ORAL ANDA 12 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 16714-128 TABLET 25 mg ORAL ANDA 15 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 16714-129 TABLET 50 mg ORAL ANDA 15 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 16714-800 TABLET 25 mg ORAL ANDA 12 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 16714-801 TABLET 50 mg ORAL ANDA 12 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 16714-936 TABLET 25 mg ORAL ANDA 12 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 16714-937 TABLET 25 mg ORAL ANDA 12 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 21695-671 TABLET 25 mg ORAL ANDA 12 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 21695-743 TABLET 25 mg ORAL ANDA 12 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 21695-744 TABLET 25 mg ORAL ANDA 12 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 29300-333 TABLET 25 mg ORAL ANDA 10 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 29300-334 TABLET 50 mg ORAL ANDA 10 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 33261-942 TABLET 25 mg ORAL ANDA 12 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 43353-149 TABLET 25 mg ORAL ANDA 12 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 43353-922 TABLET 50 mg ORAL ANDA 13 sections
CHLORTHALIDONE HUMAN PRESCRIPTION DRUG LABEL 1 43598-719 TABLET 25 mg ORAL ANDA 11 sections
CHLORTHALIDONE HUMAN PRESCRIPTION DRUG LABEL 1 43598-720 TABLET 50 mg ORAL ANDA 11 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 50090-0144 TABLET 25 mg ORAL ANDA 13 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 50090-0145 TABLET 50 mg ORAL ANDA 13 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 50090-3161 TABLET 50 mg ORAL ANDA 12 sections
CHLORTHALIDONE HUMAN PRESCRIPTION DRUG LABEL 1 50090-3190 TABLET 25 mg ORAL ANDA 12 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 50090-3910 TABLET 25 mg ORAL ANDA 12 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 50090-4223 TABLET 25 mg ORAL ANDA 13 sections
CHLORTHALIDONE HUMAN PRESCRIPTION DRUG LABEL 1 50268-167 TABLET 25 mg ORAL ANDA 11 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 51079-058 TABLET 25 mg ORAL ANDA 12 sections
TENORETIC HUMAN PRESCRIPTION DRUG LABEL 2 52427-382 TABLET 25 mg ORAL NDA 16 sections