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    Cefamandole

    FINISHED DOSAGE FORMULATIONS

    GLOBAL SALES INFORMATION

    MARKET PLACE

    PharmaCompass
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    2D Structure
    Also known as: Cefadole, 34444-01-4, Cephamandole, Cefamandol, Cephadole, Cefamandolum
    Molecular Formula
    C18H18N6O5S2
    Molecular Weight
    462.5  g/mol
    InChI Key
    OLVCFLKTBJRLHI-AXAPSJFSSA-N
    FDA UNII
    5CKP8C2LLI
    Semisynthetic wide-spectrum cephalosporin with prolonged action, probably due to beta-lactamase resistance. It is used also as the nafate.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1
    2.1.3 InChI Key
    OLVCFLKTBJRLHI-AXAPSJFSSA-N
    2.1.4 Canonical SMILES
    CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)NC(=O)C(C4=CC=CC=C4)O)SC2)C(=O)O
    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)O)SC2)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    5CKP8C2LLI
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Cephamandole

    2. Compound 83405

    2.3.2 Depositor-Supplied Synonyms

    1. Cefadole

    2. 34444-01-4

    3. Cephamandole

    4. Cefamandol

    5. Cephadole

    6. Cefamandolum

    7. L-cefamandole

    8. Compound 83405

    9. Chebi:3480

    10. (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-carboxylic Acid

    11. 5ckp8c2lli

    12. (6r,7r)-7-{[(2r)-2-hydroxy-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-carboxylic Acid

    13. Compound-83405

    14. (6r,7r)-7-[[(2r)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    15. J01dc03

    16. Kefdole

    17. 7-d-mandelamido-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-3-cephem-4-carboxylic Acid

    18. Kefamandol

    19. Mancef

    20. (6r,7r)-7-((r)-2-hydroxy-2-phenylacetamido)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    21. 7-[(2-hydroxy-2-phenylacetyl)amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    22. 30034-03-8

    23. Unii-5ckp8c2lli

    24. Cefamandol [inn-spanish]

    25. Cefamandole (usan/inn)

    26. Cefamandolum [inn-latin]

    27. Free Form

    28. Cefamandole [usan:inn:ban]

    29. Einecs 252-030-0

    30. Brn 0598510

    31. Cefamandole [mi]

    32. Prestwick0_000747

    33. Prestwick1_000747

    34. Prestwick2_000747

    35. Prestwick3_000747

    36. Cefamandole [inn]

    37. Cefamandole [usan]

    38. Epitope Id:141490

    39. Cefamandole [vandf]

    40. Cefamandole [mart.]

    41. Chembl1146

    42. Schembl37287

    43. Bspbio_000734

    44. Cefamandole [who-dd]

    45. Spbio_002673

    46. Bpbio1_000808

    47. Dtxsid7022750

    48. Gtpl12210

    49. Hy-b1128

    50. Zinc3830394

    51. Bdbm50350468

    52. Akos025401365

    53. Ac-1294

    54. Cs-4724

    55. Db01326

    56. (6r,7r)-7-[[(2r)-2-hydroxy-2-phenyl-acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    57. (6r,7r)-7-{[(2r)-2-hydroxy-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-carboxylic Acid

    58. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((hydroxyphenylacetyl)amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6alpha,7beta(r*)))-

    59. 7beta-[(2r)-2-hydroxy-2-phenylacetamido]-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylic Acid

    60. C06879

    61. D02344

    62. 444c014

    63. Cefamandole, Antibiotic For Culture Media Use Only

    64. Q2601530

    65. W-106736

    66. Brd-k27130738-236-03-4

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

    68. (6r,7r)-7-[(2r)-2-hydroxy-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-carboxylic Acid

    69. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((hydroxyphenylacetyl)amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6.alpha.,7.beta.(r*)))-

    70. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 7-[[(2r)-2-hydroxy-2-phenylacetyl]amino]-3-[[(1-methyl-1h-tetrazol-5-yl)thio]methyl]-8-oxo-, (6r,7r)-

    71. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 7-[[(2r)-2-hydroxy-2-phenylacetyl]amino]-3-[[(1-methyl-1h-tetrazol-5-yl)thio]methyl]-8-oxo-, 6r,7r)-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 462.5 g/mol
    Molecular Formula C18H18N6O5S2
    XLogP3-0.9
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count7
    Exact Mass462.07801004 g/mol
    Monoisotopic Mass462.07801004 g/mol
    Topological Polar Surface Area201 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity777
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of serious infections caused by susceptible strains of microorganisms.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    The parenteral prodrug formate ester cefamandole nafate is a broad-spectrum cephalosporin antibiotic. The bactericidal action of cefamandole results from inhibition of cell-wall synthesis. Cephalosporins have in vitro activity against a wide range of gram-positive and gram-negative organisms.

    5.2 MeSH Pharmacological Classification

    Anti-Bacterial Agents

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

    5.3 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01D - Other beta-lactam antibacterials

    J01DC - Second-generation cephalosporins

    J01DC03 - Cefamandole

    5.4 Biological Half-Life

    The half-life after an intravenous dose is 32 minutes; after intramuscular administration, the half-life is 60 minutes.

    5.5 Mechanism of Action

    Like all beta-lactam antibiotics, cefamandole binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefamandole interferes with an autolysin inhibitor.