chlortalidone ๐Ÿถ Veterinary Use | 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 ยตM/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 137.77 14.74 125 9183 96014 50499802
Hypokalaemia 50.33 14.74 71 9237 87921 50507895
Pneumonia viral 48.07 14.74 24 9284 6810 50589006
Presyncope 45.87 14.74 37 9271 24161 50571655
Cardiac murmur 42.92 14.74 26 9282 10758 50585058
Breath sounds abnormal 42.30 14.74 23 9285 7769 50588047
Milk-alkali syndrome 38.30 14.74 11 9297 674 50595142
Systemic infection 35.52 14.74 14 9294 2269 50593547
Blood pressure increased 34.71 14.74 76 9232 133056 50462760
Myxoedema coma 34.36 14.74 9 9299 390 50595426
Poor personal hygiene 31.24 14.74 8 9300 317 50595499
Diarrhoea infectious 30.84 14.74 10 9298 922 50594894
Angle closure glaucoma 30.00 14.74 12 9296 2022 50593794
Blood potassium decreased 25.98 14.74 33 9275 36912 50558904
Wheezing 25.51 14.74 43 9265 62004 50533812
Hyperlactacidaemia 24.68 14.74 11 9297 2422 50593394
Nasal congestion 24.52 14.74 38 9270 51082 50544734
Eosinophilia 24.21 14.74 23 9285 18629 50577187
Catastrophic reaction 22.77 14.74 4 9304 23 50595793
Strabismus 20.92 14.74 9 9299 1821 50593995
Cockroach allergy 20.15 14.74 4 9304 48 50595768
Blood glucose increased 18.88 14.74 41 9267 71283 50524533
Nodal rhythm 18.78 14.74 8 9300 1579 50594237
Chronic obstructive pulmonary disease 18.06 14.74 34 9274 53401 50542415
Asthma 17.83 14.74 46 9262 89291 50506525
Drug interaction 17.58 14.74 78 9230 199543 50396273
Renal impairment 17.26 14.74 41 9267 75620 50520196
Syncope 16.56 14.74 49 9259 102953 50492863
Oedema peripheral 16.46 14.74 65 9243 157896 50437920
Contraindicated product administered 15.73 14.74 4 9304 148954 50446862
Dizziness 15.60 14.74 113 9195 346256 50249560
Renal artery stenosis 15.19 14.74 7 9301 1665 50594151
Mite allergy 14.95 14.74 5 9303 508 50595308
Productive cough 14.76 14.74 31 9277 52663 50543153

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 79.08 16.63 82 5886 67551 29501008
Hypokalaemia 69.97 16.63 67 5901 50136 29518423
Renal artery stenosis 62.83 16.63 21 5947 1940 29566619
SARS-CoV-2 antibody test positive 49.06 16.63 11 5957 222 29568337
Rectal prolapse 47.41 16.63 11 5957 260 29568299
Fibrillary glomerulonephritis 44.96 16.63 8 5960 45 29568514
Intraductal papillary mucinous neoplasm 44.93 16.63 11 5957 329 29568230
Vena cava injury 44.32 16.63 10 5958 208 29568351
Renal cyst haemorrhage 43.02 16.63 11 5957 394 29568165
Choroidal effusion 36.49 16.63 8 5960 145 29568414
Abdominal wall haemorrhage 32.40 16.63 8 5960 248 29568311
Carotid arteriosclerosis 29.29 16.63 11 5957 1427 29567132
Chronic kidney disease 27.04 16.63 35 5933 36381 29532178
Dizziness 26.32 16.63 91 5877 189593 29378966
Delayed graft function 26.17 16.63 11 5957 1916 29566643
Mean cell volume increased 23.46 16.63 11 5957 2478 29566081
Presyncope 23.37 16.63 22 5946 16067 29552492
Hyperparathyroidism secondary 23.26 16.63 9 5959 1266 29567293
Actinic keratosis 21.82 16.63 12 5956 3774 29564785
Aortic arteriosclerosis 21.56 16.63 12 5956 3864 29564695
Diverticulum intestinal 20.56 16.63 11 5957 3279 29565280
Left ventricular hypertrophy 20.08 16.63 14 5954 6689 29561870
Angle closure glaucoma 19.34 16.63 7 5961 818 29567741
Amyloidosis 19.33 16.63 9 5959 1995 29566564
Hepatosplenomegaly 19.30 16.63 11 5957 3706 29564853
Hepatic steatosis 19.01 16.63 19 5949 14927 29553632
Vitamin D decreased 18.90 16.63 10 5958 2915 29565644
Cardiac failure acute 18.22 16.63 15 5953 9177 29559382
Aortic dilatation 18.04 16.63 7 5961 992 29567567
Glycosylated haemoglobin increased 17.89 16.63 15 5953 9411 29559148
Vascular anastomotic haemorrhage 17.69 16.63 4 5964 84 29568475
Spinal stenosis 17.67 16.63 11 5957 4352 29564207
Blood potassium increased 17.49 16.63 18 5950 14633 29553926
Perineal cyst 17.47 16.63 4 5964 89 29568470
Restless legs syndrome 17.30 16.63 13 5955 6971 29561588

FDA Adverse Event Reporting System (Geriatric)

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 212.31 13.58 199 12567 148140 64337826
Hypokalaemia 103.50 13.58 124 12642 121779 64364187
Renal artery stenosis 76.96 13.58 27 12739 2942 64483024
Presyncope 72.15 13.58 58 12708 35031 64450935
Angle closure glaucoma 49.69 13.58 19 12747 2638 64483328
SARS-CoV-2 antibody test positive 48.54 13.58 11 12755 238 64485728
Fibrillary glomerulonephritis 45.11 13.58 8 12758 45 64485921
Vena cava injury 43.97 13.58 10 12756 220 64485746
Pneumonia viral 43.35 13.58 24 12742 7798 64478168
Renal cyst haemorrhage 41.79 13.58 11 12755 451 64485515
Cardiac murmur 39.49 13.58 26 12740 11537 64474429
Intraductal papillary mucinous neoplasm 38.99 13.58 11 12755 586 64485380
Choroidal effusion 34.26 13.58 10 12756 602 64485364
Breath sounds abnormal 32.19 13.58 23 12743 11646 64474320
Milk-alkali syndrome 31.50 13.58 11 12755 1182 64484784
Chronic kidney disease 30.83 13.58 47 12719 57872 64428094
Myxoedema coma 28.87 13.58 9 12757 678 64485288
Syncope 28.54 13.58 82 12684 157553 64328413
Abdominal wall haemorrhage 28.53 13.58 8 12758 417 64485549
Rectal prolapse 27.54 13.58 11 12755 1715 64484251
Dizziness 26.94 13.58 161 12605 430002 64055964
Poor personal hygiene 26.86 13.58 8 12758 517 64485449
Diarrhoea infectious 26.24 13.58 10 12756 1376 64484590
Blood potassium decreased 26.19 13.58 36 12730 40363 64445603
Systemic infection 26.00 13.58 14 12752 4307 64481659
Blood pressure increased 25.85 13.58 84 12682 172468 64313498
Carotid arteriosclerosis 25.56 13.58 11 12755 2068 64483898
Catastrophic reaction 22.48 13.58 4 12762 23 64485943
Left ventricular hypertrophy 22.31 13.58 17 12749 9489 64476477
Oedema peripheral 21.90 13.58 91 12675 210226 64275740
Bradycardia 21.87 13.58 62 12704 118157 64367809
Hyperlactacidaemia 21.86 13.58 13 12753 4831 64481135
Delayed graft function 21.59 13.58 11 12755 3025 64482941
Iron deficiency anaemia 21.43 13.58 24 12742 21865 64464101
Renal impairment 21.37 13.58 67 12699 134950 64351016
Blood potassium increased 19.69 13.58 25 12741 25955 64460011
Strabismus 18.95 13.58 9 12757 2128 64483838
Mean cell volume increased 18.84 13.58 12 12754 5034 64480932
Nasal congestion 18.25 13.58 38 12728 59620 64426346
Hyperparathyroidism secondary 18.21 13.58 9 12757 2321 64483645
Chronic obstructive pulmonary disease 18.05 13.58 42 12724 71006 64414960
Vascular anastomotic haemorrhage 17.76 13.58 4 12762 84 64485882
Perineal cyst 17.68 13.58 4 12762 86 64485880
Amyloidosis 17.63 13.58 9 12757 2485 64483481
Febrile neutropenia 16.89 13.58 8 12758 187649 64298317
Blood glucose increased 16.76 13.58 50 12716 98023 64387943
Inappropriate antidiuretic hormone secretion 16.19 13.58 21 12745 22268 64463698
Actinic keratosis 16.16 13.58 11 12755 5154 64480812
Aortic dilatation 15.87 13.58 7 12759 1396 64484570
Hepatosplenomegaly 15.82 13.58 11 12755 5332 64480634
Toxicity to various agents 15.78 13.58 30 12736 363483 64122483
Blood pressure inadequately controlled 15.75 13.58 11 12755 5373 64480593
Glycosylated haemoglobin increased 14.73 13.58 17 12749 16002 64469964
Diverticulum intestinal 14.68 13.58 12 12754 7408 64478558
Asthenia 14.66 13.58 139 12627 427905 64058061
Aortic arteriosclerosis 14.60 13.58 12 12754 7464 64478502
Paraneoplastic dermatomyositis 14.54 13.58 3 12763 41 64485925
Calcium ionised decreased 14.35 13.58 5 12761 533 64485433
Vitamin D decreased 14.31 13.58 12 12754 7675 64478291
Drug interaction 14.14 13.58 121 12645 361962 64124004
Metabolic alkalosis 13.82 13.58 9 12757 3919 64482047
Nodal rhythm 13.72 13.58 8 12758 2866 64483100
Wheezing 13.69 13.58 41 12725 80538 64405428

FDA Adverse Event Reporting System (Pediatric)

None

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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
EQ 40MG MEDOXOMIL;12.5MG EDARBYCLOR AZURITY N202331 Dec. 20, 2011 RX TABLET ORAL 7572920 Jan. 7, 2025 TREATMENT OF HYPERTENSION
EQ 40MG MEDOXOMIL;25MG EDARBYCLOR AZURITY N202331 Dec. 20, 2011 RX TABLET ORAL 7572920 Jan. 7, 2025 TREATMENT OF HYPERTENSION
EQ 40MG MEDOXOMIL;12.5MG EDARBYCLOR AZURITY N202331 Dec. 20, 2011 RX TABLET ORAL 9387249 July 1, 2031 TREATMENT OF HYPERTENSION
EQ 40MG MEDOXOMIL;25MG EDARBYCLOR AZURITY 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 1 Enzyme Ki 6.46 CHEMBL
Carbonic anhydrase 4 Enzyme Ki 6.71 CHEMBL
Carbonic anhydrase 9 Enzyme Ki 7.64 CHEMBL
Carbonic anhydrase 12 Enzyme Ki 8.35 CHEMBL
Carbonic anhydrase 5A, mitochondrial Enzyme Ki 6.04 CHEMBL
Carbonic anhydrase 5B, mitochondrial Enzyme Ki 8.05 CHEMBL
Carbonic anhydrase 7 Enzyme Ki 8.55 CHEMBL
Carbonic anhydrase 3 Enzyme Ki 4.96 CHEMBL
Carbonic anhydrase 6 Enzyme Ki 5.87 CHEMBL
Carbonic anhydrase 14 Enzyme Ki 5.38 CHEMBL
Carbonic anhydrase 2 Enzyme Kd 5.56 WOMBAT-PK
Carbonic anhydrase 13 Enzyme Ki 7.82 CHEMBL

External reference:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 0378-0213 TABLET 50 mg ORAL ANDA 25 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 0378-0222 TABLET 25 mg ORAL ANDA 25 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 0591-5782 TABLET 25 mg ORAL ANDA 18 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 0591-5783 TABLET 25 mg ORAL ANDA 18 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 0904-6900 TABLET 25 mg ORAL ANDA 21 sections
ATENOLOL AND CHLORTHALIDONE HUMAN PRESCRIPTION DRUG LABEL 2 10135-733 TABLET 25 mg ORAL ANDA 21 sections
ATENOLOL AND CHLORTHALIDONE HUMAN PRESCRIPTION DRUG LABEL 2 10135-734 TABLET 25 mg ORAL ANDA 21 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 16714-128 TABLET 25 mg ORAL ANDA 16 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 16714-129 TABLET 50 mg ORAL ANDA 16 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 16714-800 TABLET 25 mg ORAL ANDA 21 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 16714-801 TABLET 50 mg ORAL ANDA 21 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 16714-936 TABLET 25 mg ORAL ANDA 16 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 16714-937 TABLET 25 mg ORAL ANDA 16 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 21695-671 TABLET 25 mg ORAL ANDA 24 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 21695-743 TABLET 25 mg ORAL ANDA 18 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 21695-744 TABLET 25 mg ORAL ANDA 18 sections
Chlorthalidone Human Prescription Drug Label 1 27241-216 TABLET 25 mg ORAL ANDA 20 sections
Chlorthalidone Human Prescription Drug Label 1 27241-217 TABLET 50 mg ORAL ANDA 20 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 29300-333 TABLET 25 mg ORAL ANDA 19 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 29300-334 TABLET 50 mg ORAL ANDA 19 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 29300-400 TABLET 25 mg ORAL ANDA 17 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 29300-401 TABLET 25 mg ORAL ANDA 17 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 33261-942 TABLET 25 mg ORAL ANDA 18 sections
Atenolol and Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 2 43353-149 TABLET 25 mg ORAL ANDA 18 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 43353-922 TABLET 50 mg ORAL ANDA 24 sections
CHLORTHALIDONE Human Prescription Drug Label 1 43598-719 TABLET 25 mg ORAL ANDA 21 sections
CHLORTHALIDONE Human Prescription Drug Label 1 43598-720 TABLET 50 mg ORAL ANDA 21 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 50090-3161 TABLET 50 mg ORAL ANDA 21 sections
CHLORTHALIDONE Human Prescription Drug Label 1 50090-3190 TABLET 25 mg ORAL ANDA 22 sections
Chlorthalidone HUMAN PRESCRIPTION DRUG LABEL 1 50090-3910 TABLET 25 mg ORAL ANDA 21 sections