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    Chemistry

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    Also known as: 42540-40-9, Cephamandole nafate, Cefamandol nafato, Kefadol, Mandokef, O-formylcefamandole sodium
    Molecular Formula
    C19H17N6NaO6S2
    Molecular Weight
    512.5  g/mol
    InChI Key
    ICZOIXFFVKYXOM-YCLOEFEOSA-M
    FDA UNII
    8HDO7941DO
    Cefamandole Nafate
    Cefamandole Nafate is the sodium salt form of cefamandole formyl ester. Cefamandole nafate is a pro-drug that is hydrolyzed by plasma esterases to produce cefamandole, a semi-synthetic beta-lactam, second-generation cephalosporin antibiotic with bactericidal activity. Cefamandole binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall. 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

    Cefamandole Nafate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    sodium;(6R,7R)-7-[[(2R)-2-formyloxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
    2.1.2 InChI
    InChI=1S/C19H18N6O6S2.Na/c1-24-19(21-22-23-24)33-8-11-7-32-17-12(16(28)25(17)13(11)18(29)30)20-15(27)14(31-9-26)10-5-3-2-4-6-10;/h2-6,9,12,14,17H,7-8H2,1H3,(H,20,27)(H,29,30);/q;+1/p-1/t12-,14-,17-;/m1./s1
    2.1.3 InChI Key
    ICZOIXFFVKYXOM-YCLOEFEOSA-M
    2.1.4 Canonical SMILES
    CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)NC(=O)C(C4=CC=CC=C4)OC=O)SC2)C(=O)[O-].[Na+]
    2.1.5 Isomeric SMILES
    CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)[C@@H](C4=CC=CC=C4)OC=O)SC2)C(=O)[O-].[Na+]
    2.2 Other Identifiers
    2.2.1 UNII
    8HDO7941DO
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Cefamandole Nafate, Monosodium Salt, (6r-(6alpha,7beta(r*)))-isomer

    2. Cefamandole Nafate, Monosodium Salt, 14c-labeled, (6r-(6alpha,7beta,(r*)))-isomer

    3. Mandol

    2.3.2 Depositor-Supplied Synonyms

    1. 42540-40-9

    2. Cephamandole Nafate

    3. Cefamandol Nafato

    4. Kefadol

    5. Mandokef

    6. O-formylcefamandole Sodium

    7. Sodium O-formylcefamandole

    8. Cemandil Sodium Salt

    9. Cefam

    10. Cefamandole Nafate Sodium

    11. 8hdo7941do

    12. Chebi:3481

    13. Cefamandole Formate Sodium Salt

    14. Cefaseptolo

    15. Lampomandol

    16. Bergacef

    17. Mandolsan

    18. Neocefal

    19. Pavecef

    20. Cedol

    21. Cefamandole Nafate [usan]

    22. Ncgc00183035-01

    23. Lilly 106223

    24. Cefamandol Nafato [spanish]

    25. Unii-8hdo7941do

    26. Kefandol

    27. Cemandil Sodium

    28. Einecs 255-877-4

    29. Mandol (tn)

    30. Mfcd00864877

    31. Nsc 299588

    32. Cefamandole Nafate [usan:usp:inn:ban]

    33. Cefamandole Formate Sodium

    34. Cefamandole Nafate, 97%

    35. Cefamandole Nafate (usp)

    36. Dsstox_cid_2751

    37. Chembl1618

    38. Dsstox_rid_76715

    39. Dsstox_gsid_22751

    40. Schembl181311

    41. Cefamandole Nafate [mi]

    42. Dtxsid2022751

    43. Cefamandole Nafate [vandf]

    44. Cefamandole Nafate [mart.]

    45. Cefamandole Nafate [usp-rs]

    46. Cefamandole Nafate [who-dd]

    47. Hy-b1166

    48. Tox21_113487

    49. Akos015895550

    50. Akos015961133

    51. Ac-1642

    52. Ccg-269787

    53. Cs-4768

    54. Gs-3575

    55. Cefamandole Nafate [orange Book]

    56. Cefamandole Nafate [ep Monograph]

    57. Cefamandole Nafate [usp Impurity]

    58. As-12360

    59. Cas-42540-40-9

    60. C-2464

    61. C08102

    62. D00909

    63. Q27106102

    64. Cefamandole Nafate, Antibiotic For Culture Media Use Only

    65. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((formyloxy)phenylacetyl)amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, Monosodium Salt, (6r-(6.alpha.,7.beta.(r*)))

    66. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((formyloxy)phenylacetyl)amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, Monosodium Salt, (6r-(6alpha,7beta(r*)))-

    67. Sodium (6r,7r)-7-((r)-2-(formyloxy)-2-phenylacetamido)-3-((1-methyl-1h-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    68. Sodium (6r,7r)-7-[(2r)-2-(formyloxy)-2-phenylacetamido]-3-{[(1-methyl-1h-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    69. Sodium (6r,7r)-7-[[(2r)-2-formyloxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    70. Sodium (6r,7r)-7-{[(2r)-2-(formyloxy)-2-phenylacetyl]amino}-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    71. Sodium (6r,7r)-7-{[(2r)-2-(formyloxy)-2-phenylacetyl]amino}-3-{[(1-methyl-1h-tetrazol-5-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    72. Sodium (6r-(6alpha,7beta(r*)))-7-(((formyloxy)phenylacetyl)amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

    73. Sodium 7beta-[(2r)-2-(formyloxy)-2-phenylacetamido]-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylate

    74. Sodium(6r,7r)-7-(r)-mandelamido-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate Formate(ester)

    2.4 Create Date
    2008-02-05
    3 Chemical and Physical Properties
    Molecular Weight 512.5 g/mol
    Molecular Formula C19H17N6NaO6S2
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count11
    Rotatable Bond Count9
    Exact Mass512.05486891 g/mol
    Monoisotopic Mass512.05486891 g/mol
    Topological Polar Surface Area210 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity844
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    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.)

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