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    Also known as: 252188-71-9, Unii-n99027v28j, Ceftobiprole medocaril (sodium), Bal5788, Ceftobiprole medocaril sodium, N99027v28j
    Molecular Formula
    C26H25N8NaO11S2
    Molecular Weight
    712.6  g/mol
    InChI Key
    MFAWUGGPPMTWPU-LCJFHXTKSA-M
    FDA UNII
    N99027V28J
    N99027V28J
    Ceftobiprole Medocaril is a water-soluble prodrug of ceftobiprole, a pyrrolidinone cephalosporin antibiotic, with bactericidal activity. Ceftobiprole binds to and inactivates penicillin-binding proteins (PBPs), enzymes involved in the terminal stages of bacterial cell wall assembly and cell wall reshaping during bacterial growth and division. This agent exhibits a broad spectrum of activity against gram-negative and gram-positive pathogens including methicillin-resistant S. aureus (MRSA), vancomycin-intermediate S. aureus (VISA) and vancomycin-resistant S. aureus (VRSA). Ceftobiprole is refractory to hydrolysis by class A and class C lactamases.
    1 2D Structure

    N99027V28J

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    sodium;(6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-hydroxyiminoacetyl]amino]-3-[(E)-[1-[(3R)-1-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methoxycarbonyl]pyrrolidin-3-yl]-2-oxopyrrolidin-3-ylidene]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
    2.1.2 InChI
    InChI=1S/C26H26N8O11S2.Na/c1-10-14(45-26(41)44-10)8-43-25(40)32-4-3-13(7-32)33-5-2-11(20(33)36)6-12-9-46-22-16(21(37)34(22)17(12)23(38)39)28-19(35)15(30-42)18-29-24(27)47-31-18;/h6,13,16,22,42H,2-5,7-9H2,1H3,(H,28,35)(H,38,39)(H2,27,29,31);/q;+1/p-1/b11-6+,30-15-;/t13-,16-,22-;/m1./s1
    2.1.3 InChI Key
    MFAWUGGPPMTWPU-LCJFHXTKSA-M
    2.1.4 Canonical SMILES
    CC1=C(OC(=O)O1)COC(=O)N2CCC(C2)N3CCC(=CC4=C(N5C(C(C5=O)NC(=O)C(=NO)C6=NSC(=N6)N)SC4)C(=O)[O-])C3=O.[Na+]
    2.1.5 Isomeric SMILES
    CC1=C(OC(=O)O1)COC(=O)N2CC[C@H](C2)N3CC/C(=C\C4=C(N5[C@@H]([C@@H](C5=O)NC(=O)/C(=N\O)/C6=NSC(=N6)N)SC4)C(=O)[O-])/C3=O.[Na+]
    2.2 Other Identifiers
    2.2.1 UNII
    N99027V28J
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Bal 5788

    2. Bal-5788

    3. Bal5788

    4. Ceftobiprole Medocaril (inn)

    5. Ceftobiprole Medocaril Free Acid

    6. Ceftobiprole Medocaril Sodium

    2.3.2 Depositor-Supplied Synonyms

    1. 252188-71-9

    2. Unii-n99027v28j

    3. Ceftobiprole Medocaril (sodium)

    4. Bal5788

    5. Ceftobiprole Medocaril Sodium

    6. N99027v28j

    7. Bal5788-001

    8. Ro 65-5788

    9. Ro-65-5788

    10. Bal-5788

    11. Sodium;(6r,7r)-7-[[(2z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-hydroxyiminoacetyl]amino]-3-[(e)-[1-[(3r)-1-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methoxycarbonyl]pyrrolidin-3-yl]-2-oxopyrrolidin-3-ylidene]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    12. Ceftobiprole Medocaril (usan)

    13. Ceftobiprole Medocaril [usan]

    14. Ceftobiprole Medocaril Sodium Salt

    15. Ro-655788

    16. Bal-5788-001

    17. Schembl4401305

    18. Dtxsid601021562

    19. Ceftobiprole Medocaril [usan:inn]

    20. Ceftobiprole Medocaril [mart.]

    21. Hy-106574a

    22. Ceftobiprole Medocaril [ema Epar]

    23. Cs-0103172

    24. Ceftobiprole Medocaril Sodium [who-dd]

    25. Ro-65-5788/001

    26. Ceftobiprole Medocaril Sodium Salt [mi]

    27. D08886

    28. (6r,7r)-7-(((2z)-(5-amino-1,2,4-thiadiazol-3-yl)(hydroxyimino)-acetyl)amino)-3-((e)-((3'r)-1'-(((5-methyl-2-oxo-1,3-dioxol-4-yl)methoxy)carbonyl)-2-oxo(1,3'-bipyrrolidin)-3-ylidene)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid Monosodium Salt

    29. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2z)-(5-amino-1,2,4-thiadiazol-3-yl) (hydroxyimino)acetyl)amino)-3-((e)-((3'r)-1'-(((5-methyl-2-oxo-1,3-dioxol-4-yl)methoxy)carbonyl)-2-oxo(1,3'-bipyrrolidin)-3-ylidene)methyl)-8-oxo-, Monosodium Salt, (6r,7r)-

    2.4 Create Date
    2019-01-15
    3 Chemical and Physical Properties
    Molecular Weight 712.6 g/mol
    Molecular Formula C26H25N8NaO11S2
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count17
    Rotatable Bond Count9
    Exact Mass712.09819027 g/mol
    Monoisotopic Mass712.09819027 g/mol
    Topological Polar Surface Area313 Ų
    Heavy Atom Count48
    Formal Charge0
    Complexity1570
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count2
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Indication

    Treatment of pneumonia

    Treatment of complicated skin and soft-tissue infections

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-Bacterial Agents

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

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