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    Ceftibuten Dihydrate

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    2D Structure
    Also known as: 118081-34-8, Ceftibuten (dihydrate), Ceftibuten.2h2o, Isocef, 62f4443rwp, Ceftibuten hydrate
    Molecular Formula
    C15H18N4O8S2
    Molecular Weight
    446.5  g/mol
    InChI Key
    SSWTVBYDDFPFAF-DKOGRLLHSA-N
    FDA UNII
    62F4443RWP
    Ceftibuten Dihydrate is the dihydrate form of ceftibuten, a semisynthetic, beta-lactamase-stable, third-generation cephalosporin with antibacterial activity. Ceftibuten binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.
    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;dihydrate
    2.1.2 InChI
    InChI=1S/C15H14N4O6S2.2H2O/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);2*1H2/b6-1-;;/t10-,13-;;/m1../s1
    2.1.3 InChI Key
    SSWTVBYDDFPFAF-DKOGRLLHSA-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.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.O.O
    2.2 Other Identifiers
    2.2.1 UNII
    62F4443RWP
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 118081-34-8

    2. Ceftibuten (dihydrate)

    3. Ceftibuten.2h2o

    4. Isocef

    5. 62f4443rwp

    6. Ceftibuten Hydrate

    7. Cetb

    8. (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;dihydrate

    9. (6r,7r)-7-[[(z)-2-(2-amino-1,3-thiazol-4-yl)-5-hydroxy-5-oxopent-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Dihydrate

    10. Seftem

    11. (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--water (1/2)

    12. 7beta-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino}-3,4-didehydrocepham-4-carboxylic Acid--water(1/2)

    13. Unii-62f4443rwp

    14. Seftem (tn)

    15. Cedax (tn)

    16. Ceftibuten Hydrate (jp17)

    17. Schembl159144

    18. Ceftibuten Hydrate [jan]

    19. Chebi:34618

    20. Hy-b0698a

    21. Ceftibuten Dihydrate [mi]

    22. Ceftibuten Dihydrate [vandf]

    23. Mfcd08141796

    24. S3623

    25. Ceftibuten Dihydrate [who-dd]

    26. Akos025149353

    27. Ccg-269195

    28. Cs-4518

    29. Ceftibuten Dihydrate [orange Book]

    30. D02121

    31. 081c348

    32. A803878

    33. Q27116185

    34. (+)-(6r,7r)-7-[2-(2-amino-1,3-thiazol-4-yl)-4-carboxy-2-butenamide]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Dihydrate

    35. (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 Dihydrate

    36. 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-, Dihydrate, (6r-(6.alpha.,7.beta.(z)))-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 446.5 g/mol
    Molecular Formula C15H18N4O8S2
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count6
    Exact Mass446.05660589 g/mol
    Monoisotopic Mass446.05660589 g/mol
    Topological Polar Surface Area219 Ų
    Heavy Atom Count29
    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 Count3