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Piretanide

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Chemistry

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Also known as: 55837-27-9, Tauliz, 4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid, Eurelix, Hoe 118, 4-phenoxy-3-(pyrrolidin-1-yl)-5-sulfamoylbenzoic acid

Molecular Formula

C₁₇H₁₈N₂O₅S

Molecular Weight

362.4 g/mol

InChI Key

UJEWTUDSLQGTOA-UHFFFAOYSA-N

FDA UNII

DQ6KK6GV93

Piretanide is a sulfamoylbenzoic acid belonging to the class of loop diuretics. Piretanide is structurally related to furosemide and bumetanide.

1 2D Structure

Piretanide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic acid

2.1.2 InChI

InChI=1S/C17H18N2O5S/c18-25(22,23)15-11-12(17(20)21)10-14(19-8-4-5-9-19)16(15)24-13-6-2-1-3-7-13/h1-3,6-7,10-11H,4-5,8-9H2,(H,20,21)(H2,18,22,23)

2.1.3 InChI Key

UJEWTUDSLQGTOA-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CCN(C1)C2=C(C(=CC(=C2)C(=O)O)S(=O)(=O)N)OC3=CC=CC=C3

2.2 Other Identifiers

2.2.1 UNII

DQ6KK6GV93

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic Acid

2. Hoe 118

2.3.2 Depositor-Supplied Synonyms

1. 55837-27-9

2. Tauliz

3. 4-phenoxy-3-pyrrolidin-1-yl-5-sulfamoylbenzoic Acid

4. Eurelix

5. Hoe 118

6. 4-phenoxy-3-(pyrrolidin-1-yl)-5-sulfamoylbenzoic Acid

7. Hoe-118

8. Benzoic Acid, 3-(aminosulfonyl)-4-phenoxy-5-(1-pyrrolidinyl)-

9. S 73 4118

10. 4-phenoxy-3-(1-pyrrolidinyl)-5-sulfamoylbenzoic Acid

11. Dq6kk6gv93

12. Ncgc00016878-01

13. Arlix

14. Cas-55837-27-9

15. Dsstox_cid_3488

16. Dsstox_rid_77050

17. Dsstox_gsid_23488

18. S-734118

19. S-73-4118

20. Piretanido [spanish]

21. Piretanido

22. Piretanidum

23. Piretanidum [inn-latin]

24. Piretanido [inn-spanish]

25. Arelix (tn)

26. Einecs 259-852-9

27. Unii-dq6kk6gv93

28. Brn 5633965

29. Piretanide [usan:inn:ban:jan]

30. Piretanide-[d4]

31. S 734118

32. 3-(aminosulfonyl)-4-phenoxy-5-(1-pyrrolidinyl)-benzoic Acid

33. Piretanide [mi]

34. Piretanide [inn]

35. Piretanide [jan]

36. Acide Phenoxy-4-(1-pyrrolidinyl)-3-sulfamoyl-5 Benzoique [french]

37. Prestwick0_001047

38. Prestwick1_001047

39. Prestwick2_001047

40. Prestwick3_001047

41. Piretanide [usan]

42. Piretanide [mart.]

43. Piretanide [who-dd]

44. Schembl49473

45. Bspbio_000974

46. Mls002154123

47. Piretanide (jan/usan/inn)

48. Spbio_002907

49. Bpbio1_001072

50. Chembl349803

51. Gtpl4742

52. Dtxsid2023488

53. Chebi:32015

54. Piretanide For System Suitability

55. Acide Phenoxy-4-(1-pyrrolidinyl)-3-sulfamoyl-5 Benzoique

56. Piretanide [ep Monograph]

57. Hms1571a16

58. Hms2098a16

59. Hms2230g15

60. Hms3372o22

61. Hms3715a16

62. Zinc3812930

63. Tox21_110661

64. Akos015895445

65. Tox21_110661_1

66. Ccg-221047

67. Db02925

68. Ncgc00016878-02

69. Ncgc00016878-04

70. Smr001233430

71. Hy-119816

72. Ab00514020

73. Cs-0078068

74. Ft-0673944

75. 2-methyl-2-propylpropane-1,3-diyl Dicarbamate

76. D01634

77. 837p279

78. A924106

79. Sr-01000838837

80. 4-phenoxy-3-(pyrrolidinyl)-5-sulfamoylbenzoic Acid

81. Q3905617

82. Sr-01000838837-2

83. W-105543

84. 3-(1-pyrrolidinyl)-4-phenoxy-5-sulphamylbenzoic Acid

85. Brd-k87990216-001-03-7

86. 4-phenoxy-3-(1-pyrrolidinyl)-5-sulphamoylbenzoic Acid

87. F2173-0688

88. 3-(aminosulfonyl)-4-(phenyloxy)-5-pyrrolidin-1-ylbenzoic Acid

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₈N₂O₅S
Molecular Weight	362.4 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	5
Exact Mass	362.09364285 g/mol
Monoisotopic Mass	362.09364285 g/mol
Topological Polar Surface Area	118 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	564
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Diuretics

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

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.)

4.2 ATC Code

C - Cardiovascular system

C03 - Diuretics

C03C - High-ceiling diuretics

C03CA - Sulfonamides, plain

C03CA03 - Piretanide

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