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    CAS-10381-75-6

    BUILDING BLOCK

    PharmaCompass
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    2D Structure
    Also known as: 10381-75-6, Bromotheophylline, 8-bromo-1,3-dimethyl-1h-purine-2,6(3h,9h)-dione, Theophylline, 8-bromo-, 8-bromo-1,3-dimethyl-7h-purine-2,6-dione, 1h-purine-2,6-dione, 8-bromo-3,7-dihydro-1,3-dimethyl-
    Molecular Formula
    C7H7BrN4O2
    Molecular Weight
    259.06  g/mol
    InChI Key
    SKTFQHRVFFOHTQ-UHFFFAOYSA-N
    FDA UNII
    FZG87K1MQ6
    Bromotheophylline is the active moiety of pamabrom, a mixture of 2-amino-2-methyl-propanol and bromotheophylline. From this mixture, bromotheophylline acts as a weak diuretic that has been used along with some analgesics to relieve the symptoms of premenstrual syndrome. Bromotheophylline is categorized on the FDA as a drug substance with an inactive state since March, 1980. It is also approved by Health Canada to be used alone or in combination with [DB00316] in OTC products.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    8-bromo-1,3-dimethyl-7H-purine-2,6-dione
    2.1.2 InChI
    InChI=1S/C7H7BrN4O2/c1-11-4-3(9-6(8)10-4)5(13)12(2)7(11)14/h1-2H3,(H,9,10)
    2.1.3 InChI Key
    SKTFQHRVFFOHTQ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN1C2=C(C(=O)N(C1=O)C)NC(=N2)Br
    2.2 Other Identifiers
    2.2.1 UNII
    FZG87K1MQ6
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 10381-75-6

    2. Bromotheophylline

    3. 8-bromo-1,3-dimethyl-1h-purine-2,6(3h,9h)-dione

    4. Theophylline, 8-bromo-

    5. 8-bromo-1,3-dimethyl-7h-purine-2,6-dione

    6. 1h-purine-2,6-dione, 8-bromo-3,7-dihydro-1,3-dimethyl-

    7. C7h7brn4o2

    8. 8-bromotheophyline

    9. 8-bromo-1,3-dimethyl-3,7-dihydro-1h-purine-2,6-dione

    10. 8-bromo-1,3-dimethyl-2,3,6,7-tetrahydro-1h-purine-2,6-dione

    11. Unii-fzg87k1mq6

    12. Fzg87k1mq6

    13. 8-bromo-1,3-dimethyl-1h-purine-2,6(3h,7h)-dione

    14. Predema

    15. 8-bromo-1,3-dimethyl-3,7-dihydro-purine-2,6-dione

    16. Chembl316160

    17. Dtxsid7044768

    18. Einecs 233-846-6

    19. Mfcd00022664

    20. Nsc 164940

    21. Nsc-164940

    22. Ncgc00167564-01

    23. 1h-purine-2,6-dione, 8-bromo-3,9-dihydro-1,3-dimethyl-

    24. Dtxcid5024768

    25. Cas-10381-75-6

    26. 8-bromo-theophylline

    27. 8-bromo-1,3-dimethyl-3,7-dihydro-1h-pyrine-2,6-dione

    28. Oprea1_299436

    29. Oprea1_509676

    30. Mls004754491

    31. Schembl237881

    32. C7-h7-br-n4-o2

    33. Tox21_112559

    34. Bbl012666

    35. Bdbm50045345

    36. Ccg-19376

    37. Mfcd01848460

    38. Nsc164940

    39. Stk803299

    40. 8-bromotheophylline [usp-rs]

    41. Akos000274376

    42. Akos001283003

    43. Tox21_112559_1

    44. Am85456

    45. Db14018

    46. Gs-5727

    47. Hy-w088152

    48. Ncgc00167564-03

    49. Ncgc00167564-04

    50. Smr002397689

    51. Sy023545

    52. B3456

    53. Cs-0130336

    54. Ft-0636693

    55. En300-17892

    56. 8-bromanyl-1,3-dimethyl-7h-purine-2,6-dione

    57. H10528

    58. Ab01300038-01

    59. Ab01300038_03

    60. A800812

    61. Af-399/37411012

    62. Sr-01000479300

    63. 1h-purine-2, 8-bromo-3,7-dihydro-1,3-dimethyl-

    64. Sr-01000479300-1

    65. W-108837

    66. Q27278353

    67. Z57161790

    68. 8-bromo-1,3-dimethyl-1h-purine-2,6(3h, 7h)-dione

    69. F0807-0406

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 259.06 g/mol
    Molecular Formula C7H7BrN4O2
    XLogP31
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count0
    Exact Mass g/mol
    Monoisotopic Mass g/mol
    Topological Polar Surface Area69.3
    Heavy Atom Count14
    Formal Charge0
    Complexity297
    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 Indication

    Bromotheophylline is used as a diuretic and also, in combination with [DB00316], it is used for the relief of temporary water weight gain, bloating, swelling and full feeling associated with the premenstrual and menstrual periods.

    5 Pharmacology and Biochemistry
    5.1 Absorption, Distribution and Excretion

    Absorption

    When administered after one single oral dosage, bromotheophylline is rapidly absorbed and it reaches a maximal plasma concentration of 2.5 mg/L in 0.78 hours. The mean residence time is registered to be of 12 hours with an AUC in the first 8 hours of 27 mg.h/L.

    Route of Elimination

    This pharmacokinetic property has not been determined.

    Volume of Distribution

    This pharmacokinetic property has not been determined.

    Clearance

    This pharmacokinetic property has not been determined.

    5.2 Metabolism/Metabolites

    This pharmacokinetic property has not been determined.

    5.3 Biological Half-Life

    The apparent elimination half-life is registered to be 21.35 hours.

    5.4 Mechanism of Action

    Bromotheophylline is part of the group of the xanthines. As part of this group, it is thought that bromotheophylline increases the permeability of the renal tubule, increases glomerular filtration rate and inhibits the sodium reabsorption in the proximal tubule. It is thought but not confirmed that pamabrom as a mixture seems to have an additional mechanism of action in which the presence of 2-amino-2-methyl-1-propanol produces the suppression of the antidiuretic hormone in the posterior pituitary gland.