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    Ceftibuten

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

    GLOBAL SALES INFORMATION

    MARKET PLACE

    PATENTS & EXCLUSIVITIES

    REF. STANDARDS & IMPURITIES

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    2D Structure
    Also known as: 97519-39-6, Cedax, Ceftibuteno, Ceftibutenum, Ceftibutene, Sch 39720
    Molecular Formula
    C15H14N4O6S2
    Molecular Weight
    410.4  g/mol
    InChI Key
    UNJFKXSSGBWRBZ-BJCIPQKHSA-N
    FDA UNII
    IW71N46B4Y
    A cephalosporin antibacterial agent that is used in the treatment of infections, including urinary-tract and respiratory-tract infections.
    Ceftibuten is a Cephalosporin Antibacterial.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C15H14N4O6S2/c16-15-17-7(5-27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-8(14(24)25)3-4-26-13(10)19/h1,3,5,10,13H,2,4H2,(H2,16,17)(H,18,22)(H,20,21)(H,24,25)/b6-1-/t10-,13-/m1/s1
    2.1.3 InChI Key
    UNJFKXSSGBWRBZ-BJCIPQKHSA-N
    2.1.4 Canonical SMILES
    C1C=C(N2C(S1)C(C2=O)NC(=O)C(=CCC(=O)O)C3=CSC(=N3)N)C(=O)O
    2.1.5 Isomeric SMILES
    C1C=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)/C(=C\CC(=O)O)/C3=CSC(=N3)N)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    IW71N46B4Y
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 7-(2-(2-amino-4-thiazolyl)-4-carboxy-2-butenoylamino)-3-cephem-4-carboxylic Acid

    2. 7432 S

    3. 7432-s

    4. Cedax

    5. Sch 39720

    6. Sch-39720

    7. Sch39720

    2.3.2 Depositor-Supplied Synonyms

    1. 97519-39-6

    2. Cedax

    3. Ceftibuteno

    4. Ceftibutenum

    5. Ceftibutene

    6. Sch 39720

    7. Ceftibuten Hydrate

    8. Cis-ceftibuten

    9. Sch-39720

    10. 7432-s

    11. Antibiotic 7432s

    12. Nsc-758925

    13. Achn383

    14. Achn-383

    15. Chebi:3510

    16. Iw71n46b4y

    17. (+)-(6r,7r)-7-((z)-2-(2-amino-4-thiazolyl)-4-carboxycrotonamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

    18. Ceftibuten Dihydrate

    19. Cis-ceftibutin

    20. 97519-39-6 (free)

    21. Isocef

    22. Cetb

    23. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((2-(2-amino-4-thiazolyl)-4-carboxy-1-oxo-2-butenyl)amino)-8-oxo-, (6r-(6alpha,7beta(z)))-

    24. Cephalosporin 7432-s

    25. (6r,7r)-7-[[(z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    26. (6r,7r)-7-((z)-2-(2-aminothiazol-4-yl)-4-carboxybut-2-enamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    27. Ceftibutene [inn-french]

    28. Ceftibutenum [inn-latin]

    29. Ceftibuteno [inn-spanish]

    30. Unii-iw71n46b4y

    31. Ceftibutin

    32. Ceprifran

    33. Ceftem

    34. Keimax

    35. Ceftibuten [usan:inn:ban]

    36. S 7432

    37. Ncgc00095137-01

    38. Ceftibuten-13c3

    39. Ceftibuten, 95%

    40. Mfcd00864918

    41. Ceftibuten [mi]

    42. Ceftibuten [inn]

    43. Ceftibuten (usan/inn)

    44. Spectrum5_001558

    45. Ceftibuten [usan]

    46. Ceftibuten [vandf]

    47. Ceftibutin [vandf]

    48. Ceftibuten [who-dd]

    49. Chembl1605

    50. Dsstox_cid_25925

    51. Dsstox_rid_81227

    52. Dsstox_gsid_45925

    53. Schembl37054

    54. Bspbio_002733

    55. Spectrum1505207

    56. Dtxsid4045925

    57. Gtpl12029

    58. Hms1922l17

    59. Hms2093k18

    60. Hms3715p10

    61. Pharmakon1600-01505207

    62. Hy-b0698

    63. Zinc3871967

    64. Tox21_111446

    65. Bdbm50370586

    66. Ccg-39440

    67. Nsc758925

    68. Akos005146205

    69. Akos015854930

    70. Db01415

    71. Nsc 758925

    72. Ncgc00178501-01

    73. Ncgc00178501-04

    74. Sbi-0206740.p001

    75. Cas-97519-39-6

    76. C-2550

    77. C08117

    78. D00922

    79. Ab01563048_01

    80. 519c396

    81. Ceftibuten, Antibiotic For Culture Media Use Only

    82. Q419521

    83. Sr-05000001989

    84. Sr-05000001989-1

    85. 7-[2-(2-amino-1,3-thiazol-4-yl)-4-carboxyisocrotonamide]-3-cephem-4-carboxylicacid

    86. (6r,7r)-7-[(2z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    87. (6r,7r)-7-[[(2z)-2-(2-amino-4-thiazolyl)-4-carboxy-1-oxo-2-buten-1-yl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    88. (6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    89. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((2-(2-amino-4-thiazolyl)-4-carboxy-1-oxo-2-butenyl)amino)-8-oxo-, (6r-(6.alpha.,7.beta.(z)))-

    90. 7beta-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino}-3,4-didehydrocepham-4-carboxylic Acid

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 410.4 g/mol
    Molecular Formula C15H14N4O6S2
    XLogP3-0.3
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count6
    Exact Mass410.03547653 g/mol
    Monoisotopic Mass410.03547653 g/mol
    Topological Polar Surface Area217 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity755
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameCedax
    PubMed HealthCeftibuten (By mouth)
    Drug ClassesAntibiotic
    Drug LabelCEDAX (ceftibuten capsules) and (ceftibuten for oral suspension) contain the active ingredient ceftibuten as ceftibuten dihydrate. Ceftibuten dihydrate is a semisynthetic cephalosporin antibiotic for oral administration. Chemically, it is (+)-(6R,7R)...
    Active IngredientCeftibuten dihydrate
    Dosage FormCapsule; For suspension
    RouteOral
    Strengtheq 180mg base/5ml; eq 90mg base/5ml; eq 400mg base
    Market StatusPrescription
    CompanyPernix Therap

    2 of 2  
    Drug NameCedax
    PubMed HealthCeftibuten (By mouth)
    Drug ClassesAntibiotic
    Drug LabelCEDAX (ceftibuten capsules) and (ceftibuten for oral suspension) contain the active ingredient ceftibuten as ceftibuten dihydrate. Ceftibuten dihydrate is a semisynthetic cephalosporin antibiotic for oral administration. Chemically, it is (+)-(6R,7R)...
    Active IngredientCeftibuten dihydrate
    Dosage FormCapsule; For suspension
    RouteOral
    Strengtheq 180mg base/5ml; eq 90mg base/5ml; eq 400mg base
    Market StatusPrescription
    CompanyPernix Therap

    4.2 Drug Indication

    Indicated for the treatment of acute bacterial exacerbations of chronic bronchitis (ABECB), acute bacterial otitis media, pharyngitis, and tonsilitis.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Ceftibuten is an antibiotic with bactericidal actions.

    5.2 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    CEFTIBUTEN
    5.3.2 FDA UNII
    IW71N46B4Y
    5.3.3 Pharmacological Classes
    Chemical Structure [CS] - Cephalosporins
    5.4 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01D - Other beta-lactam antibacterials

    J01DD - Third-generation cephalosporins

    J01DD14 - Ceftibuten

    5.5 Absorption, Distribution and Excretion

    Absorption

    Rapidly absorbed following oral administration.

    Route of Elimination

    Ceftibuten is excreted in the urine; 95% of the administered radioactivity was recovered either in urine or feces.

    Volume of Distribution

    0.21 L/kg [adult subjects]

    0.5 L/kg [fasting pediatric patients]

    5.6 Metabolism/Metabolites

    A study with radiolabeled ceftibuten administered to 6 healthy adult male volunteers demonstrated that cis-ceftibuten is the predominant component in both plasma and urine. About 10% of ceftibuten is converted to the trans-isomer is approximately 1/8 as antimicrobially potent as the cis-isomer.

    5.7 Mechanism of Action

    Ceftibuten exerts its bactericidal action by binding to essential target proteins of the bacterial cell wall. This binding leads to inhibition of cell-wall synthesis.