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    Chemistry

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    Also known as: Torasemide, 56211-40-6, Demadex, Luprac, Torasemida, Torasemidum
    Molecular Formula
    C16H20N4O3S
    Molecular Weight
    348.4  g/mol
    InChI Key
    NGBFQHCMQULJNZ-UHFFFAOYSA-N
    FDA UNII
    W31X2H97FB
    Torsemide
    A pyridine and sulfonamide derivative that acts as a sodium-potassium chloride symporter inhibitor (loop diuretic). It is used for the treatment of EDEMA associated with CONGESTIVE HEART FAILURE; CHRONIC RENAL INSUFFICIENCY; and LIVER DISEASES. It is also used for the management of HYPERTENSION.
    Torsemide is a Loop Diuretic. The physiologic effect of torsemide is by means of Increased Diuresis at Loop of Henle.
    1 2D Structure

    Torsemide

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[4-(3-methylanilino)pyridin-3-yl]sulfonyl-3-propan-2-ylurea
    2.1.2 InChI
    InChI=1S/C16H20N4O3S/c1-11(2)18-16(21)20-24(22,23)15-10-17-8-7-14(15)19-13-6-4-5-12(3)9-13/h4-11H,1-3H3,(H,17,19)(H2,18,20,21)
    2.1.3 InChI Key
    NGBFQHCMQULJNZ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC(=CC=C1)NC2=C(C=NC=C2)S(=O)(=O)NC(=O)NC(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    W31X2H97FB
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-isopropyl-3-((4-(3-methylphenylamino)pyridine)-3-sulfonyl)urea

    2. 1-isopropyl-3-((4-m-toluidino-3-pyridyl)sulfonyl)urea

    3. Demadex

    4. Torasemide

    2.3.2 Depositor-Supplied Synonyms

    1. Torasemide

    2. 56211-40-6

    3. Demadex

    4. Luprac

    5. Torasemida

    6. Torasemidum

    7. Torasemidum [inn-latin]

    8. Torasemida [inn-spanish]

    9. Unat

    10. Ac-4464

    11. Torasemide Anhydrous

    12. Jdl 464

    13. Torem

    14. Bm-02015

    15. Ac4464

    16. N-(isopropylcarbamoyl)-4-(m-tolylamino)pyridine-3-sulfonamide

    17. Soaanz

    18. Upcard

    19. 1-isopropyl-3-((4-m-toluidino-3-pyridyl)sulfonyl)urea

    20. Ac 4464

    21. Jdl-464

    22. Bm 02015

    23. 1-[4-(3-methylanilino)pyridin-3-yl]sulfonyl-3-propan-2-ylurea

    24. Torasemide [inn]

    25. Torsemide (demadex)

    26. Torasemide, Anhydrous

    27. Bm02.015

    28. N-(((1-methylethyl)amino)carbonyl)-4-((3-methylphenyl)amino)-3-pyridinesulfonamide

    29. Bm-02.015

    30. Mls001165687

    31. Chebi:9637

    32. W31x2h97fb

    33. 3-pyridinesulfonamide, N-(((1-methylethyl)amino)carbonyl)-4-((3-methylphenyl)amino)-

    34. Torsemide [usan]

    35. Ncgc00016879-01

    36. Smr000466313

    37. Toradiur

    38. Cas-56211-40-6

    39. 1-{4-[(3-methylphenyl)amino]pyridine-3-sulfonyl}-3-(propan-2-yl)urea

    40. Dsstox_cid_3690

    41. N-[(isopropylamino)carbonyl]-4-[(3-methylphenyl)amino]pyridine-3-sulfonamide

    42. 3-pyridinesulfonamide, N-[[(1-methylethyl)amino]carbonyl]-4-[(3-methylphenyl)amino]-

    43. Dsstox_rid_77149

    44. Dsstox_gsid_23690

    45. Dilutol

    46. Torocard

    47. Sutril

    48. Torrem

    49. Torasemide N

    50. 4-[(3-methylphenyl)amino]-n-(propan-2-ylcarbamoyl)pyridine-3-sulfonamide

    51. N-{[(1-methylethyl)amino]carbonyl}-4-[(3-methylphenyl)amino]pyridine-3-sulfonamide

    52. Torsemide (usp)

    53. Demadex (tn)

    54. Luprac (tn)

    55. Ccris 6736

    56. Torasemide (jan/inn)

    57. Torsemide [usan:usp]

    58. Gj-1090

    59. Brn 0498515

    60. Unii-w31x2h97fb

    61. Mfcd00866166

    62. Ks-1123

    63. Pw-2132

    64. Spectrum_001776

    65. Torsemide [mi]

    66. Torasemide [jan]

    67. Prestwick0_001030

    68. Prestwick1_001030

    69. Prestwick2_001030

    70. Prestwick3_001030

    71. Spectrum2_001142

    72. Spectrum3_001832

    73. Spectrum4_000290

    74. Spectrum5_001699

    75. Torsemide [vandf]

    76. Torasemide [mart.]

    77. Torsemide [usp-rs]

    78. Chembl1148

    79. Torasemide [who-dd]

    80. Schembl41184

    81. Bspbio_001219

    82. Bspbio_003503

    83. Kbiogr_000820

    84. Kbioss_002257

    85. Cid_41781

    86. Mls000759418

    87. Mls001195611

    88. Mls001424121

    89. Mls006010744

    90. Bidd:gt0623

    91. Spectrum1505211

    92. Spbio_001063

    93. Spbio_003080

    94. Bpbio1_001341

    95. Gtpl7312

    96. Zinc5823

    97. Torsemide [orange Book]

    98. Dtxsid2023690

    99. Torsemide [usp Impurity]

    100. Bdbm64107

    101. Kbio2_002256

    102. Kbio2_004824

    103. Kbio2_007392

    104. Kbio3_003008

    105. Torasemide For System Suitability

    106. Torasemide [ep Monograph]

    107. Torsemide [usp Monograph]

    108. Hms1571m21

    109. Hms1922n05

    110. Hms2051l21

    111. Hms2098m21

    112. Hms2234n14

    113. Hms3373g20

    114. Hms3393l21

    115. Hms3715m21

    116. Hms3744g19

    117. Albb-027267

    118. Bcp07286

    119. Hy-b0247

    120. Tox21_110662

    121. Ccg-40257

    122. S1698

    123. Stl388026

    124. Torsemide, >=98% (hplc), Solid

    125. Akos015894937

    126. Tox21_110662_1

    127. Bm02015

    128. Db00214

    129. Nc00238

    130. Ncgc00016879-02

    131. Ncgc00016879-03

    132. Ncgc00016879-04

    133. Ncgc00016879-06

    134. Ncgc00016879-07

    135. Ncgc00095141-01

    136. Ncgc00095141-02

    137. Ncgc00095141-03

    138. Ac-18762

    139. Ab00514011

    140. Ft-0630689

    141. Ft-0675300

    142. T2538

    143. D00382

    144. T72621

    145. Ab00514011-09

    146. Ab00514011_10

    147. Ab00514011_11

    148. 211t406

    149. A830961

    150. Q419948

    151. Sr-01000759362

    152. Torasemide Anhydrous [ema Epar Veterinary]

    153. Q-201846

    154. Sr-01000759362-5

    155. Brd-k30480208-001-05-2

    156. Torsemide, United States Pharmacopeia (usp) Reference Standard

    157. 1-isopropyl-3-((4-m-toluidino-3-pyridyl)sulphonyl)urea

    158. 4-(3-methylanilino)-n-(propan-2-ylcarbamoyl)pyridine-3-sulfonamide

    159. Torasemide Anhydrous, European Pharmacopoeia (ep) Reference Standard

    160. 1-isopropyl-3-[[4-(3-methylanilino)-3-pyridyl]sulfonyl]urea;torsemide

    161. N-(isopropylcarbamoyl)-4-[(3-methylphenyl)amino]pyridine-3-sulfonamide

    162. N-[(propan-2-yl)carbamoyl]-4-[(3-methylphenyl)amino]pyridine-3-sulfonamide

    163. N-({4-[(3-methylphenyl)imino]-1,4-dihydropyridin-3-yl}sulfonyl)propane-2-carbamimidic Acid

    164. Torasemide For System Suitability, European Pharmacopoeia (ep) Reference Standard

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 348.4 g/mol
    Molecular Formula C16H20N4O3S
    XLogP32.7
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count5
    Exact Mass348.12561169 g/mol
    Monoisotopic Mass348.12561169 g/mol
    Topological Polar Surface Area109 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity518
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    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 NameDemadex
    PubMed HealthTorsemide
    Drug ClassesCardiovascular Agent
    Drug LabelDEMADEX (torsemide) is a diuretic of the pyridine-sulfonylurea class. Its chemical name is 1-isopropyl-3-[(4-m-toluidino-3-pyridyl) sulfonyl] urea and its structural formula is:Its empirical formula is C16H20N4O3S, its pKa is 7.1, and its molecular...
    Active IngredientTorsemide
    Dosage FormTablet
    RouteOral
    Strength5mg; 100mg; 10mg; 20mg
    Market StatusPrescription
    CompanyMeda Pharms

    2 of 4  
    Drug NameTorsemide
    PubMed HealthTorsemide
    Drug ClassesCardiovascular Agent
    Drug LabelDEMADEX (torsemide) is a diuretic of the pyridine-sulfonylurea class. Its chemical name is 1-isopropyl-3-[(4-m-toluidino-3-pyridyl) sulfonyl] urea and its structural formula is:Its empirical formula is C16H20N4O3S, its pKa is 7.1, and its molecular...
    Active IngredientTorsemide
    Dosage FormTablet; Injectable
    RouteInjection; Oral
    Strength50mg/5ml (10mg/ml); 5mg; 20mg/2ml (10mg/ml); 100mg; 10mg; 20mg
    Market StatusPrescription
    CompanyVintage Pharms; Teva; Apotex; Hetero Labs Ltd Iii; Pliva Pharm Ind; Sun Pharm Inds; Aurobindo Pharma; Par Pharm; Roxane; Luitpold; Eurohlth Intl

    3 of 4  
    Drug NameDemadex
    PubMed HealthTorsemide
    Drug ClassesCardiovascular Agent
    Drug LabelDEMADEX (torsemide) is a diuretic of the pyridine-sulfonylurea class. Its chemical name is 1-isopropyl-3-[(4-m-toluidino-3-pyridyl) sulfonyl] urea and its structural formula is:Its empirical formula is C16H20N4O3S, its pKa is 7.1, and its molecular...
    Active IngredientTorsemide
    Dosage FormTablet
    RouteOral
    Strength5mg; 100mg; 10mg; 20mg
    Market StatusPrescription
    CompanyMeda Pharms

    4 of 4  
    Drug NameTorsemide
    PubMed HealthTorsemide
    Drug ClassesCardiovascular Agent
    Drug LabelDEMADEX (torsemide) is a diuretic of the pyridine-sulfonylurea class. Its chemical name is 1-isopropyl-3-[(4-m-toluidino-3-pyridyl) sulfonyl] urea and its structural formula is:Its empirical formula is C16H20N4O3S, its pKa is 7.1, and its molecular...
    Active IngredientTorsemide
    Dosage FormTablet; Injectable
    RouteInjection; Oral
    Strength50mg/5ml (10mg/ml); 5mg; 20mg/2ml (10mg/ml); 100mg; 10mg; 20mg
    Market StatusPrescription
    CompanyVintage Pharms; Teva; Apotex; Hetero Labs Ltd Iii; Pliva Pharm Ind; Sun Pharm Inds; Aurobindo Pharma; Par Pharm; Roxane; Luitpold; Eurohlth Intl

    4.2 Drug Indication

    Torasemide is indicated for the treatment of edema associated with congestive heart failure, renal or hepatic diseases. From this condition, it has been observed that torasemide is very effective in cases of kidney failure. As well, torasemide is approved to be used as an antihypertensive agent either alone or in combination with other antihypertensives.

    FDA Label

    For treatment of clinical signs, including oedema and effusion, related to congestive heart failure in dogs.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    It is widely known that administration of torasemide can attenuate renal injury and reduce the severity of acute renal failure. This effect is obtained by increasing urine output and hence, facilitating fluid, acid-base and potassium control. This effect is obtained by the increase in the excretion of urinary sodium and chloride. Several reports have indicated that torasemide presents a long-lasting diuresis and less potassium excretion which can be explained by the effect that torasemide has on the renin-angiotensin-aldosterone system. This effect is very similar to the effect observed with the administration of combination therapy with [furosemide] and [spironolactone] and it is characterized by a decrease in plasma brain natriuretic peptide and improved measurements of left ventricular function. Above the aforementioned effect, torasemide presents a dual effect .in which the inhibition of aldosterone which donates torasemide with a potassium-sparing action. Torasemide has been shown to reduce extracellular fluid volume and blood pressure in hypertensive patients suffering from chronic kidney disease. As well, some reports have indicated that torasemide can reduce myocardial fibrosis by reducing the collagen accumulation. This effect is suggested to be related to the decrease in aldosterone which in order has been shown to reduce the production of the enzyme procollagen type I carboxy-terminal proteinase which is known to be overexpressed in heart failure patients.

    5.2 MeSH Pharmacological Classification

    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.)

    Sodium Potassium Chloride Symporter Inhibitors

    Agents that inhibit SODIUM-POTASSIUM-CHLORIDE SYMPORTERS which are concentrated in the thick ascending limb at the junction of the LOOP OF HENLE and KIDNEY TUBULES, DISTAL. They act as DIURETICS. Excess use is associated with HYPOKALEMIA and HYPERGLYCEMIA. (See all compounds classified as Sodium Potassium Chloride Symporter Inhibitors.)

    Diuretics

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

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    TORSEMIDE
    5.3.2 FDA UNII
    W31X2H97FB
    5.3.3 Pharmacological Classes
    Loop Diuretic [EPC]; Increased Diuresis at Loop of Henle [PE]
    5.4 ATC Code

    QC03CA04

    C03CA04

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    C - Cardiovascular system

    C03 - Diuretics

    C03C - High-ceiling diuretics

    C03CA - Sulfonamides, plain

    C03CA04 - Torasemide

    5.5 Absorption, Distribution and Excretion

    Absorption

    Torasemide is the diuretic with the highest oral bioavailability even in advanced stages of chronic kidney disease. This bioavailability tends to be higher than 80% regardless of the patient condition. The maximal serum concentration is reported to be of 1 hour and the absorption parameters are not affected by its use concomitantly with food.

    Route of Elimination

    Torasemide is mainly hepatically processed and excreted in the feces from which about 70-80% of the administered dose is excreted by this pathway. On the other hand, about 20-30% of the administered dose is found in the urine.

    Volume of Distribution

    The volume of distribution of torasemide is 0.2 L/kg.

    Clearance

    The clearance rate of torasemide is considerably reduced by the presence of renal disorders.

    5.6 Metabolism/Metabolites

    Torasemide is extensively metabolized in the liver and only 20% of the dose remains unchanged and it is recovered in the urine. Metabolized via the hepatic CYP2C8 and CYP2C9 mainly by reactions of hydroxylation, oxidation and reduction to 5 metabolites. The major metabolite, M5, is pharmacologically inactive. There are 2 minor metabolites, M1, possessing one-tenth the activity of torasemide, and M3, equal in activity to torasemide. Overall, torasemide appears to account for 80% of the total diuretic activity, while metabolites M1 and M3 account for 9% and 11%, respectively.

    Torasemide has known human metabolites that include N-[(4-{[3-(hydroxymethyl)phenyl]imino}-1,4-dihydropyridin-3-yl)sulfonyl]propane-2-carbamimidic acid.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    The average half-life of torasemide is 3.5 hours.

    5.8 Mechanism of Action

    As mentioned above, torasemide is part of the loop diuretics and thus, it acts by reducing the oxygen demand in the medullary thick ascending loop of Henle by inhibiting the Na+/K+/Cl- pump on the luminal cell membrane surface. This action is obtained by the binding of torasemide to a chloride ion-binding site of the transport molecule. Torasemide is known to have an effect in the renin-angiotensin-aldosterone system by inhibiting the downstream cascade after the activation of angiotensin II. This inhibition will produce a secondary effect marked by the reduction of the expression of aldosterone synthase, TGF-B1 and thromboxane A2 and a reduction on the aldosterone receptor binding.

    API Reference Price

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    14-Jan-2021
    21-Nov-2024
    KGS
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    DOSAGE - TABLET;ORAL - 100MG **Federal Regist...DOSAGE - TABLET;ORAL - 100MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 20136

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    DOSAGE - TABLET;ORAL - 10MG **Federal Registe...DOSAGE - TABLET;ORAL - 10MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 20136

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    DOSAGE - TABLET;ORAL - 20MG **Federal Registe...DOSAGE - TABLET;ORAL - 20MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 20136

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    DOSAGE - TABLET;ORAL - 5MG **Federal Register...DOSAGE - TABLET;ORAL - 5MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 20136

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