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Azosemide

Azosemide

Synopsis, Chemistry

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Also known as: 27589-33-9, Azosemid, Diart, Azosemida, Azosemidum, Luret

Molecular Formula

C₁₂H₁₁ClN₆O₂S₂

Molecular Weight

370.8 g/mol

InChI Key

HMEDEBAJARCKCT-UHFFFAOYSA-N

FDA UNII

MR40VT1L8Z

Azosemide is a monosulfamyl belonging to the class of loop diuretics. Azosemide inhibits sodium and chloride reabsorption throughout the thick ascending limb of the loop of Henle.

1 2D Structure

Azosemide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-chloro-5-(2H-tetrazol-5-yl)-4-(thiophen-2-ylmethylamino)benzenesulfonamide

2.1.2 InChI

InChI=1S/C12H11ClN6O2S2/c13-9-5-10(15-6-7-2-1-3-22-7)8(12-16-18-19-17-12)4-11(9)23(14,20)21/h1-5,15H,6H2,(H2,14,20,21)(H,16,17,18,19)

2.1.3 InChI Key

HMEDEBAJARCKCT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CSC(=C1)CNC2=CC(=C(C=C2C3=NNN=N3)S(=O)(=O)N)Cl

2.2 Other Identifiers

2.2.1 UNII

MR40VT1L8Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-chloro-5-(1h-tetrazol-5-yl)-n(sup 4)-2-thenylsulfanilamide

2. 5-(4-chloro-5-sulfamyl-2-thienylaminophenyl)tetrazole

3. Azosemid

4. Benzenesulfonamide, 2-chloro-5-(1h-tetrazol-5-yl)-4-((2-thienylmethyl)amino)-

5. Bm 02.001

6. Ple 1053

2.3.2 Depositor-Supplied Synonyms

1. 27589-33-9

2. Azosemid

3. Diart

4. Azosemida

5. Azosemidum

6. Luret

7. 2-chloro-5-(2h-tetrazol-5-yl)-4-((thiophen-2-ylmethyl)amino)benzenesulfonamide

8. Ple 1053

9. 2-chloro-5-(1h-tetrazol-5-yl)-n(sup 4)-2-thenylsulfanilamide

10. Mr40vt1l8z

11. 2-chloro-5-(2h-tetrazol-5-yl)-4-(thiophen-2-ylmethylamino)benzenesulfonamide

12. Chebi:31248

13. Sulfanilamide, 2-chloro-5-(1h-tetrazol-5-yl)-n(sup 4)-2-thenyl-

14. Benzenesulfonamide, 2-chloro-5-(1h-tetrazol-5-yl)-4-((2-thienylmethyl)amino)-

15. 5-(4'-chloro-5'-sulfamoyl-2'-thenylaminophenyl)tetrazole

16. Ncgc00181340-01

17. Dsstox_cid_26910

18. Dsstox_rid_82008

19. Dsstox_gsid_46910

20. 2-chloro-5-(1h-tetrazol-5-yl)-n4-2-thenylsulfanilamide

21. Azosemidum [inn-latin]

22. Azosemida [inn-spanish]

23. 2-chloro-5-(1h-tetrazol-5-yl)-4-[(thiophen-2-ylmethyl)amino]benzenesulfonamide

24. Azosemide [usan:inn:jan]

25. Cas-27589-33-9

26. Einecs 248-549-7

27. Sk-110

28. Unii-mr40vt1l8z

29. Brn 1178491

30. Diart (tn)

31. 5-(4'-chloro-5'-sulfamoyl-2'-thenylaminophenyl)-tetrazole

32. Azosemide [inn]

33. Azosemide [jan]

34. Azosemide [mi]

35. Azosemide [usan]

36. Azosemide [mart.]

37. Azosemide [who-dd]

38. Schembl48976

39. Azosemide (jp17/usan/inn)

40. Chembl1097235

41. Dtxsid7046910

42. Amy7468

43. Ex-a1266

44. Zinc5843546

45. Tox21_112799

46. Ac-096

47. Mfcd30541344

48. Sk 110

49. Akos015961824

50. Tox21_112799_1

51. Db08961

52. Benzenesulfonamide, 2-chloro-5-(2h-tetrazol-5-yl)-4-[(2-thienylmethyl)amino]-

53. Ncgc00181340-02

54. As-12235

55. Db-047249

56. Hy-107321

57. Cs-0028137

58. Ft-0602886

59. C74435

60. D01323

61. 589a339

62. A913169

63. Q4832859

64. 5-(4-chloro-5-sulfamoyl-2-thenylaminophenyl)-tetrazole

65. 2-chloro-5-(1h-tetrazol-5-yl)-n(4)-2-thenylsulfanilamide

66. 2-chloro-5-(1h-tetrazol-5-yl)-4-(thiophen-2-ylmethylamino)benzenesulfonamide

67. 2-chloro-5-(2h-1,2,3,4-tetrazol-5-yl)-4-[(thiophen-2-ylmethyl)amino]benzene-1-sulfonamide

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₁ClN₆O₂S₂
Molecular Weight	370.8 g/mol
XLogP3	1.5
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	5
Exact Mass	370.0073437 g/mol
Monoisotopic Mass	370.0073437 g/mol
Topological Polar Surface Area	163 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	504
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 Pharmacology

Diuretic affects upon oral administration match those of furosemide. However, upon intravenous administration azosemide displays 5.5 to 8 times greater effect.

4.2 MeSH Pharmacological Classification

Diuretics

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

4.3 Absorption, Distribution and Excretion

Absorption

Peak plasma concentrations are achieved in 3-4 hours when azosemide is administered to healthy humans in a fasting state. There is an absorption lag time of approximately 1 hour. Oral bioavailability estimated to be 20.4%

Route of Elimination

Total body clearance 112ml/min. Renal clearance 41.6ml/min. Actively secreted in the renal proximal tubule of humans. This may or may not involve a nonspecific organic acid secretory pathway. There is thus a potential for disease states and other organic acids such as NSAIDs which affect the organic acid transport pathway to affect the efficacy of azosemide.

Volume of Distribution

Poor affinity for human tissue. Small apparent post-pseudodistribution Vd of 0.262 l/kg.

4.4 Metabolism/Metabolites

Considerable first pass metabolism which makes parentral administration more effective than oral administration. Eleven metabolites of azosemide were found in rats, but only azosemide and its glucuronide were detected in humans.

4.5 Biological Half-Life

Terminal half life 2-3 hours.

4.6 Mechanism of Action

Exact mechanism of action is unclear. However, it acts primarily on the loop of Henle, in both the medullary and cortical segments of the thick ascending limb.