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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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12-Jan-2021
28-Aug-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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