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    CHEMBL2103872

    PharmaCompass
    Xls

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    2D Structure
    Also known as: Ceftolozane, Cxa-101 free base, Cxa-101, Chembl2103872
    Molecular Formula
    C23H30N12O8S2
    Molecular Weight
    666.7  g/mol
    InChI Key
    JHFNIHVVXRKLEF-DCZLAGFPSA-N
    Ceftolozane is a semi-synthetic, broad-spectrum, fifth-generation cephalosporin antibiotic with bactericidal activity against certain Gram-negative and Gram-positive bacteria. Upon administration, ceftolozane binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. This interferes with the final transpeptidation step required to form peptidoglycan chain cross-links, which are a key component of and provide strength and rigidity to the bacterial cell wall. This inhibits bacterial cell wall synthesis and reduces cell wall stability, which weakens the bacterial cell wall and causes bacterial cell lysis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[(Z)-[2-[[(6R,7R)-3-[[3-amino-4-(2-aminoethylcarbamoylamino)-2-methylpyrazol-1-ium-1-yl]methyl]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl]amino]-1-(5-amino-1,2,4-thiadiazol-3-yl)-2-oxoethylidene]amino]oxy-2-methylpropanoate
    2.1.2 InChI
    InChI=1S/C23H30N12O8S2/c1-23(2,20(40)41)43-31-11(15-30-21(26)45-32-15)16(36)29-12-17(37)35-13(19(38)39)9(8-44-18(12)35)6-34-7-10(14(25)33(34)3)28-22(42)27-5-4-24/h7,12,18,25H,4-6,8,24H2,1-3H3,(H7,26,27,28,29,30,32,36,38,39,40,41,42)/b31-11-/t12-,18-/m1/s1
    2.1.3 InChI Key
    JHFNIHVVXRKLEF-DCZLAGFPSA-N
    2.1.4 Canonical SMILES
    CC(C)(C(=O)[O-])ON=C(C1=NSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C[N+]4=CC(=C(N4C)N)NC(=O)NCCN)C(=O)O
    2.1.5 Isomeric SMILES
    CC(C)(C(=O)[O-])O/N=C(/C1=NSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC(=C(N4C)N)NC(=O)NCCN)C(=O)O
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Ceftolozane

    2. Ceftolozane Sulfate

    3. Cxa-101

    4. Fr 264205

    5. Fr-264205

    6. Fr26 4205

    7. Fr264205

    2.2.2 Depositor-Supplied Synonyms

    1. Ceftolozane

    2. Cxa-101 Free Base

    3. Cxa-101

    4. Chembl2103872

    2.3 Create Date
    2013-05-30
    3 Chemical and Physical Properties
    Molecular Weight 666.7 g/mol
    Molecular Formula C23H30N12O8S2
    XLogP3-3.2
    Hydrogen Bond Donor Count7
    Hydrogen Bond Acceptor Count16
    Rotatable Bond Count11
    Exact Mass666.17509831 g/mol
    Monoisotopic Mass666.17509831 g/mol
    Topological Polar Surface Area356 Ų
    Heavy Atom Count45
    Formal Charge0
    Complexity1280
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Anti-Bacterial Agents

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