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    Chemistry

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    Also known as: 75975-70-1, Cephradine hydrate, Cephradine (monohydrate), Fuc0d71izn, (6r,7r)-7-[[(2r)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrate, Cefradine monohydrate
    Molecular Formula
    C16H21N3O5S
    Molecular Weight
    367.4  g/mol
    InChI Key
    VHNPSPMQGXQSET-CYJZLJNKSA-N
    FDA UNII
    FUC0D71IZN
    Cephradine Monohydrate
    Cephradine Monohydrate is the monohydrate form of cephradine, a beta-lactam, first-generation cephalosporin antibiotic with bactericidal activity. Cephradine monohydrate binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall. PBPs participate in the terminal stages of assembling the bacterial cell wall, and in reshaping the cell wall during cell 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

    Cephradine Monohydrate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6R,7R)-7-[[(2R)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrate
    2.1.2 InChI
    InChI=1S/C16H19N3O4S.H2O/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9;/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23);1H2/t10-,11-,15-;/m1./s1
    2.1.3 InChI Key
    VHNPSPMQGXQSET-CYJZLJNKSA-N
    2.1.4 Canonical SMILES
    CC1=C(N2C(C(C2=O)NC(=O)C(C3=CCC=CC3)N)SC1)C(=O)O.O
    2.1.5 Isomeric SMILES
    CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CCC=CC3)N)SC1)C(=O)O.O
    2.2 Other Identifiers
    2.2.1 UNII
    FUC0D71IZN
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 75975-70-1

    2. Cephradine Hydrate

    3. Cephradine (monohydrate)

    4. Fuc0d71izn

    5. (6r,7r)-7-[[(2r)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;hydrate

    6. Cefradine Monohydrate

    7. 31828-50-9

    8. Unii-fuc0d71izn

    9. Cephradinemonohydrate

    10. Schembl956675

    11. Chembl4303427

    12. Dtxsid00860560

    13. Cephradine Monohydrate [mi]

    14. S5296

    15. Akos025310716

    16. Cefradine Monohydrate [who-dd]

    17. Ccg-268254

    18. Hy-128449

    19. Cs-0099494

    20. Q27278208

    21. (6r,7r)-7-((r)-2-amino-2-(1,4-cyclohexadien-1-yl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid Monohydrate

    2.4 Create Date
    2007-12-05
    3 Chemical and Physical Properties
    Molecular Weight 367.4 g/mol
    Molecular Formula C16H21N3O5S
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count4
    Exact Mass367.12019195 g/mol
    Monoisotopic Mass367.12019195 g/mol
    Topological Polar Surface Area139 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity697
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2

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