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    DIGITAL CONTENT

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    2D Structure
    Also known as: 96187-53-0, 6-fluoro-2-(2'-fluoro-[1,1'-biphenyl]-4-yl)-3-methylquinoline-4-carboxylic acid, Brequinar [inn], Brequinarum, Biphenquinate, 6-fluoro-2-(2'-fluorobiphenyl-4-yl)-3-methylquinoline-4-carboxylic acid
    Molecular Formula
    C23H15F2NO2
    Molecular Weight
    375.4  g/mol
    InChI Key
    PHEZJEYUWHETKO-UHFFFAOYSA-N
    FDA UNII
    5XL19F49H6
    Brequinar is a synthetic quinolinecarboxylic acid analogue with antineoplastic properties. Brequinar inhibits the enzyme dihydroorotate dehydrogenase, thereby blocking de novo pyrimidine biosynthesis. This agent may also enhance the in vivo antitumor effect of antineoplastic agents such as 5-FU. (NCI04)
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methylquinoline-4-carboxylic acid
    2.1.2 InChI
    InChI=1S/C23H15F2NO2/c1-13-21(23(27)28)18-12-16(24)10-11-20(18)26-22(13)15-8-6-14(7-9-15)17-4-2-3-5-19(17)25/h2-12H,1H3,(H,27,28)
    2.1.3 InChI Key
    PHEZJEYUWHETKO-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=C(C2=C(C=CC(=C2)F)N=C1C3=CC=C(C=C3)C4=CC=CC=C4F)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    5XL19F49H6
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 6-fluoro-2-(2'-fluoro-1,1'-biphenyl-4-yl)-3-methyl-4-quinolinecarboxylic Acid

    2. 6-fluoro-2-(2'-fluoro-1,1'-biphenyl-4-yl)-3-methyl-4-quinolinecarboxylic Acid Sodium

    3. Brequinar Potassium

    4. Brequinar Sodium

    5. Brequinar Sodium Salt

    6. Dup 785

    7. Dup-785

    8. Nsc 368390

    9. Nsc-368390

    2.3.2 Depositor-Supplied Synonyms

    1. 96187-53-0

    2. 6-fluoro-2-(2'-fluoro-[1,1'-biphenyl]-4-yl)-3-methylquinoline-4-carboxylic Acid

    3. Brequinar [inn]

    4. Brequinarum

    5. Biphenquinate

    6. 6-fluoro-2-(2'-fluorobiphenyl-4-yl)-3-methylquinoline-4-carboxylic Acid

    7. Nsc 368390

    8. 6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methylquinoline-4-carboxylic Acid

    9. Dup785

    10. 5xl19f49h6

    11. Bipenquinate

    12. Nsc368390

    13. Brequinarum [latin]

    14. 6-fluoro-2-[4-(2-fluorophenyl)phenyl]-3-methyl-quinoline-4-carboxylic Acid

    15. 4-quinolinecarboxylic Acid, 6-fluoro-2-(2'-fluoro(1,1'-biphenyl)-4-yl)-3-methyl-

    16. 6-fluoro-2-(2'-fluoro-1,1'-biphenyl-4-yl)-3-methylquinoline-4-carboxylic Acid

    17. Brequinarum [inn-latin]

    18. 4-quinolinecarboxylic Acid, 6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-methyl-

    19. Unii-5xl19f49h6

    20. 6-fluoro-2-{2'-fluoro-[1,1'-biphenyl]-4-yl}-3-methylquinoline-4-carboxylic Acid

    21. Brequinar [mi]

    22. Brequinar [who-dd]

    23. Neuro_000208

    24. Schembl49400

    25. Chembl38434

    26. Dup785; Biphenquinate; Bpq

    27. Gtpl7406

    28. Bdbm15339

    29. Dtxsid00242165

    30. Tqr0591

    31. Chebi:177387

    32. Hms3749m07

    33. Amy36630

    34. Bcp06006

    35. Ex-a1515

    36. Zinc1587011

    37. Mfcd00866437

    38. S6626

    39. Akos016001465

    40. Cs-7842

    41. Db03523

    42. 4-quinolinecarboxylic Acid,6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4- Yl)-3-methyl-

    43. Ncgc00480786-05

    44. Ac-35372

    45. Ds-15411

    46. Nci60_003391

    47. Db-080409

    48. Hy-108325

    49. B5707

    50. Ft-0757290

    51. C77324

    52. A847266

    53. J-515994

    54. Bpq; Biphenquinate; Dup 785; Dup785; Dup-785

    55. Q27075486

    56. Z2465619914

    57. 6-fluoro-2-(2'-fluoro[biphenyl]-4-yl)-3-methylquinoline-4-carboxylic Acid

    58. 2-(2'-fluoro-1,1'-biphenyl-4-yl)-6-fluoro-3-methyl-4-quinolinecarboxylic Acid

    59. 6-fluoro-2-(2'-fluoro-[11'-biphenyl]-4-yl)-3-methylquinoline-4-carboxylic Acid

    60. 6-fluoro-2-(2'-fluoro-1,1 '-biphe-nyl-4-yl)-3-methyl-4-quinolinecarboxylic Acid

    61. 6-fluoro-2-(2'-fluoro-4-biphenylyl)-3-methyl-4-quinolinecarboxylate

    62. 6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-methyl-4-quinolinecarboxylic Acid

    63. 6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-methyl-4-quinolinecarboxylic Acid #

    64. 6-fluoro-2-(2'-fluoro[1,1'-biphenyl]-4-yl)-3-methylquinoline-4-carboxylic Acid

    65. 6-fluoro-2-(2'-fluoro-[1,1'-biphenyl]-4-yl)-3-methyl-4-quinolinecarboxylic Acid, (*sodium Sal*)

    2.4 Create Date
    2005-03-28
    3 Chemical and Physical Properties
    Molecular Weight 375.4 g/mol
    Molecular Formula C23H15F2NO2
    XLogP35.6
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count3
    Exact Mass375.10708505 g/mol
    Monoisotopic Mass375.10708505 g/mol
    Topological Polar Surface Area50.2 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity551
    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 MeSH Pharmacological Classification

    Immunosuppressive Agents

    Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    Antineoplastic Agents

    Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)