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    Azosemide

    ACTIVE PHARMA INGREDIENTS

    MARKET PLACE

    PharmaCompass
    $ API Ref.Price (USD/KG) : 704Xls

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    2D Structure
    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

    2D Structure

    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 Weight 370.8 g/mol
    Molecular Formula C12H11ClN6O2S2
    XLogP31.5
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count5
    Exact Mass370.0073437 g/mol
    Monoisotopic Mass370.0073437 g/mol
    Topological Polar Surface Area163 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity504
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.