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    Chemistry

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    Also known as: 77-36-1, Chlortalidone, Phthalamudine, Chlorphthalidolone, Hygroton, Chlorthalidon
    Molecular Formula
    C14H11ClN2O4S
    Molecular Weight
    338.8  g/mol
    InChI Key
    JIVPVXMEBJLZRO-UHFFFAOYSA-N
    FDA UNII
    Q0MQD1073Q
    Chlorthalidone
    A benzenesulfonamide-phthalimidine that tautomerizes to a BENZOPHENONES form. It is considered a thiazide-like diuretic.
    Chlorthalidone is a Thiazide-like Diuretic. The physiologic effect of chlorthalidone is by means of Increased Diuresis.
    1 2D Structure

    Chlorthalidone

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-chloro-5-(1-hydroxy-3-oxo-2H-isoindol-1-yl)benzenesulfonamide
    2.1.2 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)
    2.1.3 InChI Key
    JIVPVXMEBJLZRO-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC=C2C(=C1)C(=O)NC2(C3=CC(=C(C=C3)Cl)S(=O)(=O)N)O
    2.2 Other Identifiers
    2.2.1 UNII
    Q0MQD1073Q
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Chlorphthalidolone

    2. Chlortalidone

    3. Hygroton

    4. Oxodoline

    5. Phthalamudine

    6. Thalitone

    2.3.2 Depositor-Supplied Synonyms

    1. 77-36-1

    2. Chlortalidone

    3. Phthalamudine

    4. Chlorphthalidolone

    5. Hygroton

    6. Chlorthalidon

    7. Phthalamodine

    8. Natriuran

    9. Thalitone

    10. Chlorothalidone

    11. Chlorphthalidone

    12. Saluretin

    13. Zambesil

    14. Igroton

    15. Isoren

    16. Oradil

    17. Renon

    18. Hydro-long

    19. Chlortalidonum

    20. Oxodolin

    21. Oksodolin (oxodolin)

    22. Racemic Chlorthalidone

    23. 2-chloro-5-(1-hydroxy-3-oxoisoindolin-1-yl)benzenesulfonamide

    24. Demi-regroton

    25. G-33182

    26. 2-chloro-5-(1-hydroxy-3-oxo-1-isoindolinyl)benzenesulfonamide

    27. 1-keto-3-(3'-sulfamyl-4'-chlorophenyl)-3-hydroxyisoindoline

    28. 3-hydroxy-3-(4-chloro-3-sulfamylphenyl)phthalimidine

    29. 2-chloro-5-(1-hydroxy-3-oxo-2h-isoindol-1-yl)benzenesulfonamide

    30. 3-(4'-chloro-3'-sulfamoylphenyl)-3-hydroxyphthalimidine

    31. 1-oxo-3-(3-sulfamyl-4-chlorophenyl)-3-hydroxyisoindoline

    32. G 33182

    33. Nsc-69200

    34. Benzenesulfonamide, 2-chloro-5-(2,3-dihydro-1-hydroxy-3-oxo-1h-isoindol-1-yl)-

    35. Chlortalidone [inn]

    36. Benzenesulfonamide, 2-chloro-5-(1-hydroxy-3-oxo-1-isoindolinyl)-

    37. 2-chloro-5-(1-hydroxy-3-oxo-2,3-dihydro-1h-isoindol-1-yl)benzenesulfonamide

    38. Mls000069531

    39. Chebi:3654

    40. Q0mqd1073q

    41. Clortalidone

    42. Famolin

    43. Higroton

    44. Urolin

    45. 2-chloro-5-(2,3-dihydro-1-hydroxy-3-oxo-1h-isoindol-1-yl)benzenesulfonamide

    46. Clortalidona

    47. Smr000058635

    48. (+-)-hygroton

    49. Clortalidone [dcit]

    50. (+-)-chlorthalidone

    51. Dsstox_cid_2812

    52. 2-chloro-5-(1-hydroxy-3-oxo-2,3-dihydro-1h-isoindol-1-yl)benzene-1-sulfonamide

    53. Dsstox_rid_76738

    54. Dsstox_gsid_22812

    55. Chlortalidonum [inn-latin]

    56. Clortalidona [inn-spanish]

    57. Thalitone (tn)

    58. Hygroton (tn)

    59. Chlorthalidone (usp)

    60. Hsdb 3035

    61. Sr-01000721929

    62. Einecs 201-022-5

    63. Nsc 69200

    64. Chlortalidone (jan/inn)

    65. Brn 0312295

    66. Chlorthalidone [usan:usp]

    67. Unii-q0mqd1073q

    68. Oksodolin

    69. Cas-77-36-1

    70. Ncgc00016317-01

    71. Prestwick_759

    72. Regroton (salt/mix)

    73. Combipres (salt/mix)

    74. Spectrum_000146

    75. Opera_id_138

    76. (.+/-.)-hygroton

    77. Prestwick0_000351

    78. Prestwick1_000351

    79. Prestwick2_000351

    80. Prestwick3_000351

    81. Spectrum2_000099

    82. Spectrum3_000349

    83. Spectrum4_000957

    84. Spectrum5_000743

    85. (.+/-.)-chlorthalidone

    86. Chlortalidone [jan]

    87. Chlorthalidone [mi]

    88. Chembl1055

    89. Schembl26234

    90. Bspbio_000441

    91. Bspbio_002017

    92. Chlorthalidone [hsdb]

    93. Chlorthalidone [usan]

    94. Kbiogr_001574

    95. Kbioss_000626

    96. 5-22-07-00602 (beilstein Handbook Reference)

    97. Chlortalidone [mart.]

    98. Chlorthalidone (chlortalidone)

    99. Chlorthalidone [vandf]

    100. Divk1c_000731

    101. Spectrum1500187

    102. Spbio_000058

    103. Spbio_002362

    104. Chlortalidone [who-dd]

    105. Chlortalidone [who-ip]

    106. Bpbio1_000487

    107. Gtpl7147

    108. Chlorthalidone [usp-rs]

    109. Dtxsid4022812

    110. Bdbm25900

    111. Hms502e13

    112. Kbio1_000731

    113. Kbio2_000626

    114. Kbio2_003194

    115. Kbio2_005762

    116. Kbio3_001237

    117. Ninds_000731

    118. Hms1569g03

    119. Hms1920m09

    120. Hms2091e12

    121. Hms2096g03

    122. Hms2236d07

    123. Hms3259h04

    124. Hms3372a07

    125. Hms3713g03

    126. Pharmakon1600-01500187

    127. Chlortalidone [ep Impurity]

    128. Bcp27835

    129. Nsc69200

    130. Chlortalidone [ep Monograph]

    131. Chlorthalidone [orange Book]

    132. Tox21_110369

    133. Ccg-38917

    134. Mfcd00036257

    135. Nsc756692

    136. S3074

    137. Stk686335

    138. Chlortalidone 1.0 Mg/ml In Methanol

    139. Chlortalidonum [who-ip Latin]

    140. Chlorthalidone [usp Monograph]

    141. Akos005599810

    142. Tox21_110369_1

    143. Db00310

    144. Ks-1342

    145. Nc00690

    146. Nsc-756692

    147. Clorpres Component Chlorthalidone

    148. Idi1_000731

    149. Kerledex Component Chlorthalidone

    150. Regroton Component Chlorthalidone

    151. Combipres Component Chlorthalidone

    152. Ncgc00094616-01

    153. Ncgc00094616-02

    154. Ncgc00094616-03

    155. Ncgc00094616-04

    156. Ncgc00094616-07

    157. Tenoretic Component Chlorthalidone

    158. Ac-11367

    159. Hy-15833

    160. Chlorthalidone Component Of Clorpres

    161. Chlorthalidone Component Of Kerledex

    162. Chlorthalidone Component Of Regroton

    163. Sbi-0051313.p003

    164. Chlorthalidone Component Of Combipres

    165. Chlorthalidone Component Of Tenoretic

    166. Db-056211

    167. Lopressidone Component Chlorthalidone

    168. [(3,5-difluorophenyl)amino](oxo)aceticacid

    169. Ab00051946

    170. Demi-regroton Component Chlorthalidone

    171. C76474

    172. Chlorthalidone Component Of Lopressidone

    173. D00272

    174. Ab00051946_12

    175. Chlorthalidone Component Of Demi-regroton

    176. 036c257

    177. A839067

    178. Q425289

    179. Sr-01000721929-2

    180. Sr-01000721929-3

    181. W-104322

    182. Brd-a26384407-001-05-3

    183. Brd-a26384407-001-15-2

    184. 2-chloro-5-(1-hydroxy-3-oxo-1h-isoindolinyl)benzenesulfonamide

    185. Chlorthalidone, European Pharmacopoeia (ep) Reference Standard

    186. 2-chloro-5-(1,3-dihydroxy-1h-isoindol-1-yl)benzene-1-sulfonamide

    187. Benzenesulfonamide,3-dihydro-1-hydroxy-3-oxo-1h-isoindol-1-yl)-

    188. Chlorthalidone, United States Pharmacopeia (usp) Reference Standard

    189. 2-chloro-5-(1-hydroxy-3-oxo-2,3-dihydro-1h-isoindol-1-yl)benzenesulfonamide #

    190. 2-chloro-5-[(1s)-1-hydroxy-3-oxo-isoindolin-1-yl]benzenesulfonamide;chlorthalidone

    191. Chlortalidone For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    192. 74658-80-3

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 338.8 g/mol
    Molecular Formula C14H11ClN2O4S
    XLogP30.9
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count2
    Exact Mass338.0128057 g/mol
    Monoisotopic Mass338.0128057 g/mol
    Topological Polar Surface Area118 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity564
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameChlorthalidone
    PubMed HealthChlorthalidone (By mouth)
    Drug ClassesCardiovascular Agent
    Drug LabelChlorthalidone is an oral antihypertensive/diuretic. It is a monosulfamyl diuretic that differs chemically from thiazide diuretics in that a double-ring system is incorporated in its structure. It is 2-chloro-5(1-hydroxy-3-oxo-1- isoindolinyl) benzen...
    Active IngredientChlorthalidone
    Dosage FormTablet
    RouteOral
    Strength25mg; 50mg
    Market StatusPrescription
    CompanyMylan

    2 of 4  
    Drug NameThalitone
    PubMed HealthChlorthalidone (By mouth)
    Drug ClassesCardiovascular Agent
    Drug LabelThalitone (chlorthalidone USP) is an antihypertensive/diuretic supplied as 15 mg tablets for oral use. It is a monosulfamyl diuretic that differs chemically from thiazide diuretics in that a double ring system is incorporated in its structure. It i...
    Active IngredientChlorthalidone
    Dosage FormTablet
    RouteOral
    Strength15mg
    Market StatusPrescription
    CompanyCitron Pharma

    3 of 4  
    Drug NameChlorthalidone
    PubMed HealthChlorthalidone (By mouth)
    Drug ClassesCardiovascular Agent
    Drug LabelChlorthalidone is an oral antihypertensive/diuretic. It is a monosulfamyl diuretic that differs chemically from thiazide diuretics in that a double-ring system is incorporated in its structure. It is 2-chloro-5(1-hydroxy-3-oxo-1- isoindolinyl) benzen...
    Active IngredientChlorthalidone
    Dosage FormTablet
    RouteOral
    Strength25mg; 50mg
    Market StatusPrescription
    CompanyMylan

    4 of 4  
    Drug NameThalitone
    PubMed HealthChlorthalidone (By mouth)
    Drug ClassesCardiovascular Agent
    Drug LabelThalitone (chlorthalidone USP) is an antihypertensive/diuretic supplied as 15 mg tablets for oral use. It is a monosulfamyl diuretic that differs chemically from thiazide diuretics in that a double ring system is incorporated in its structure. It i...
    Active IngredientChlorthalidone
    Dosage FormTablet
    RouteOral
    Strength15mg
    Market StatusPrescription
    CompanyCitron Pharma

    4.2 Therapeutic Uses

    Antihypertensive Agents; Diuretics, Sulfamyl

    National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

    ...ORALLY EFFECTIVE DIURETIC USEFUL IN TREATMENT OF EDEMA ASSOC WITH CONGESTIVE HEART FAILURE, RENAL DISEASE, HEPATIC CIRRHOSIS, PREGNANCY, OBESITY, & PREMENSTRUAL SYNDROME. DIURETIC EFFECTS START WITHIN 2 HR AFTER ADMIN, REACH PEAK IN 6 HR, & PERSIST FOR 48 TO 72 HR.

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 871

    MOST OF THIAZIDES ARE GIVEN IN DIVIDED DAILY DOSES FOR TREATMENT OF HYPERTENSION, BUT SINGLE DAILY DOSE MAY BE PREFERABLE FOR MOBILIZATION OF EDEMA FLUID. ...CHLORTHALIDONE...SHOULD BE GIVEN LESS FREQUENTLY, SINCE.../IT HAS/ DURATION OF ACTION LONGER THAN 24 HR.

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 832

    CHLORTHALIDONE ALSO EXERTS ANTIHYPERTENSIVE EFFECT & MAY BE ADMIN WITH OTHER AGENTS, SUCH AS RESERPINE, GANGLIONIC BLOCKING AGENTS, HYDRALAZINE, & GUANETHIDINE. SINCE.../IT/ CONTAINS SULFONAMIDE GROUP, ITS PHARMACOLOGICAL ACTIONS & MANY OF ITS UNTOWARD EFFECTS ARE SIMILAR TO THOSE OF OTHER ORALLY ADMIN DIURETICS.

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 871

    For more Therapeutic Uses (Complete) data for CHLORTHALIDONE (11 total), please visit the HSDB record page.

    4.3 Drug Warning

    CHLORTHALIDONE IS CONTRAINDICATED IN PT WITH SEVERE RENAL OR HEPATIC DISEASE. PT ON THIS DRUG SHOULD BE WATCHED CLOSELY FOR SYMPTOMS OF RENAL DAMAGE OR OF ELECTROLYTE DISTURBANCE.

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 871

    May suppress lactation ... /Thiazide diuretics; from table/

    Young, L.Y., M.A. Koda-Kimble (eds.). Applied Therapeutics. The Clinical Use of Drugs. 6th ed. Vancouver, WA., Applied Therapeutics, Inc. 1995., p. 45-29

    Many experts consider diuretics contraindicated in pregnancy except for patients with heart disease, since they do not prevent or alter course of toxemia and may decrease placental perfusion. /Chlorothiazide; from table/

    Young, L.Y., M.A. Koda-Kimble (eds.). Applied Therapeutics. The Clinical Use of Drugs. 6th ed. Vancouver, WA., Applied Therapeutics, Inc. 1995., p. 45-9

    Maternal Medication usually Compatible with Breast-Feeding: Chlorthalidone: Reported Sign or Symptom in Infant or Effect on Lactation: Excreted slowly. /from Table 6/

    Report of the American Academy of Pediatrics Committee on Drugs in Pediatrics 93 (1): 140 (1994)

    For more Drug Warnings (Complete) data for CHLORTHALIDONE (14 total), please visit the HSDB record page.

    4.4 Minimum/Potential Fatal Human Dose

    3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).

    Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-239

    4.5 Drug 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.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Sodium Chloride Symporter Inhibitors

    Agents that inhibit SODIUM CHLORIDE SYMPORTERS. They act as DIURETICS. Excess use is associated with HYPOKALEMIA. (See all compounds classified as Sodium Chloride Symporter Inhibitors.)

    Diuretics

    Agents that promote the excretion of urine through their effects on kidney function. (See all compounds classified as Diuretics.)

    Antihypertensive Agents

    Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    CHLORTHALIDONE
    5.2.2 FDA UNII
    Q0MQD1073Q
    5.2.3 Pharmacological Classes
    Thiazide-like Diuretic [EPC]; Increased Diuresis [PE]
    5.3 ATC Code

    C - Cardiovascular system

    C03 - Diuretics

    C03B - Low-ceiling diuretics, excl. thiazides

    C03BA - Sulfonamides, plain

    C03BA04 - Chlortalidone

    5.4 Absorption, Distribution and Excretion

    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.

    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.

    BIOCHEM STUDIES SUGGEST THAT PROLONGED DURATION OF ACTION IS DUE TO SLOW GI ABSORPTION & ENTEROHEPATIC RECIRCULATION. DRUG IS EXCRETED UNCHANGED BY KIDNEY.

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 871

    MOST /THIAZIDE/ COMPD ARE RAPIDLY EXCRETED WITHIN 3 TO 6 HR. /THIAZIDE COMPD/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 831

    STUDY OF DOSE-DEPENDENT URINARY EXCRETION OF CHLORTHALIDONE.

    FLEUREN HLJ ET AL; DOSE-DEPENDENT URINARY EXCRETION OF CHLORTHALIDONE; CLIN PHARMACOL THER 25(6) 806-812 (1979)

    5.5 Metabolism/Metabolites

    Liver

    5.6 Biological Half-Life

    40-50 hours

    5.7 Mechanism of Action

    Chlorthalidone prevents reabsorption of sodium and chloride through inhibition of the Na+/Cl- symporter in the cortical diluting segment of the ascending limb of the loop of Henle. 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. 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 anhydrasedependent pathways. These pathways may play a role in chlorthalidone's cardiovascular risk reduction effects.

    ...ACT BY INHIBITING RENAL TUBULAR TRANSPORT OF VARIOUS IONS.

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 871

    Decreased plasma volume and decreased extracellular fluid volume; decreased cardiac output initially, followed by decreased total peripheral resistance with normalization of cardiac output ... /from table/

    Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 552

    ...ANTIHYPERTENSIVE EFFECT OF CHLORTHALIDONE IS THOUGHT TO BE DUE TO DECR CARDIAC OUTPUT.

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 862

    The exact mechanism for reduction of arterial blood pressure by diuretics is not certain. Initially the drugs decrease extracellular volume and cardiac output. However, the hypotensive effect is maintained during long-term therapy because of reduced vascular resistance ... /Diuretics/

    Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 781

    For more Mechanism of Action (Complete) data for CHLORTHALIDONE (8 total), please visit the HSDB record page.

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    14-Jan-2021
    30-Aug-2024
    KGS
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    DOSAGE - TABLET;ORAL - 100MG;25MG

    USFDA APPLICATION NUMBER - 18760

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    DOSAGE - TABLET;ORAL - EQ 40MG MEDOXOMIL;12.5...DOSAGE - TABLET;ORAL - EQ 40MG MEDOXOMIL;12.5MG

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    USFDA APPLICATION NUMBER - 86831

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