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Xipamide

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Chemistry

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Also known as: 14293-44-8, 4-chloro-n-(2,6-dimethylphenyl)-2-hydroxy-5-sulfamoylbenzamide, Diurexan, Xipamid, Aquaphor, Diurex (lacer)

Molecular Formula

C₁₅H₁₅ClN₂O₄S

Molecular Weight

354.8 g/mol

InChI Key

MTZBBNMLMNBNJL-UHFFFAOYSA-N

FDA UNII

4S9EY0NUEC

A sulfamoylbenzamide analog of CLOPAMIDE. It is diuretic and saluretic with antihypertensive activity. It is bound to PLASMA PROTEINS, thus has a delayed onset and prolonged action.

1 2D Structure

Xipamide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-chloro-N-(2,6-dimethylphenyl)-2-hydroxy-5-sulfamoylbenzamide

2.1.2 InChI

InChI=1S/C15H15ClN2O4S/c1-8-4-3-5-9(2)14(8)18-15(20)10-6-13(23(17,21)22)11(16)7-12(10)19/h3-7,19H,1-2H3,(H,18,20)(H2,17,21,22)

2.1.3 InChI Key

MTZBBNMLMNBNJL-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(C(=CC=C1)C)NC(=O)C2=CC(=C(C=C2O)Cl)S(=O)(=O)N

2.2 Other Identifiers

2.2.1 UNII

4S9EY0NUEC

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Xipamid

2.3.2 Depositor-Supplied Synonyms

1. 14293-44-8

2. 4-chloro-n-(2,6-dimethylphenyl)-2-hydroxy-5-sulfamoylbenzamide

3. Diurexan

4. Xipamid

5. Aquaphor

6. Diurex (lacer)

7. Aquaphor (diuretic)

8. Mjf 10,938

9. Be 1293

10. 4-chloro-5-sulfamoyl-2',6'-salicyloxylidide

11. Mjf-10938

12. Benzamide, 5-(aminosulfonyl)-4-chloro-n-(2,6-dimethylphenyl)-2-hydroxy-

13. Be-1293

14. 4s9ey0nuec

15. 2',6'-salicyloxylidide, 4-chloro-5-sulfamoyl-

16. 4-chlor-5-sulfamoyl-2',6'-salicyloxylidid

17. Xipamide (usan)

18. Ncgc00182543-01

19. Aquaphoril

20. Xipamide [usan]

21. Zipix

22. Aquaphor(tm), Original Formula Ointment Base

23. Dsstox_cid_3744

24. Dsstox_rid_77179

25. Dsstox_gsid_23744

26. Chronexan

27. Xipamida

28. Xipamidum

29. Xipamidum [inn-latin]

30. Xipamida [inn-spanish]

31. Xipamide [usan:inn:ban]

32. Cas-14293-44-8

33. Einecs 238-216-4

34. Unii-4s9ey0nuec

35. Mjf 10938

36. Brn 2778357

37. Lumitens

38. 4-chlor-5-sulfamoyl-2',6'-salicyloxylidid [german]

39. Xipamide [inn]

40. Xipamide [mi]

41. Xipamide [mart.]

42. Xipamide [who-dd]

43. Schembl43532

44. Chembl517199

45. Gtpl7900

46. Dtxsid5023744

47. Chebi:135499

48. Zinc538538

49. 4-chloro-n-(2,6-dimethylphenyl)-2-hydroxy-5-sulfamoyl-benzamide

50. Bei-1293

51. Tox21_112975

52. 5-(aminosulfonyl)-4-chloro-n-(2,6-dimethylphenyl)-2-hydroxybenzamide

53. Ac-911

54. Mfcd00865927

55. S5076

56. Akos015889012

57. Tox21_112975_1

58. Ccg-268092

59. Cs-w023041

60. Db13803

61. Ds-1401

62. Hy-w042301

63. Ncgc00182543-02

64. Ft-0659690

65. Ft-0675876

66. X0079

67. 4-chloro-5-sulfamoyl-2',6'-salicyloxilidide

68. 4-chloro-5-sulfamoyl-2?,6?-salicyloxylidide

69. D06341

70. 293x448

71. A807988

72. Q600951

73. Q-201936

74. 4-chloro-n-(2,6-dimethylphenyl)-2-hydroxy-5-sulphamoylbenzamide

75. 4-chloro-n-(2,6-dimethylphenyl)-2-hydroxy-5-sulfamoyl-benzamide;xipamide

76. 5-(aminosulfonyl)-4-chloro-n-(2,6-dimethylphenyl)-2-hydroxy-benzamide

77. 5-(aminosulfonyl)-4-chloro-n-(2,6-dimethylphenyl)-2-hydroxybenzamide #

78. Benzamide,5-(aminosulfonyl)-4-chloro-n-(2,6-dimethylphenyl)-2-hydroxy-

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₅ClN₂O₄S
Molecular Weight	354.8 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	354.0441058 g/mol
Monoisotopic Mass	354.0441058 g/mol
Topological Polar Surface Area	118 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	526
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.)

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.)

4.2 ATC Code

C - Cardiovascular system

C03 - Diuretics

C03B - Low-ceiling diuretics, excl. thiazides

C03BA - Sulfonamides, plain

C03BA10 - Xipamide

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