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    CAS-87239-81-4

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: Vantin, Banan, 87239-81-4, Orelox, Doxef, Cs-807
    Molecular Formula
    C21H27N5O9S2
    Molecular Weight
    557.6  g/mol
    InChI Key
    LTINZAODLRIQIX-FBXRGJNPSA-N
    FDA UNII
    2TB00A1Z7N
    Cefpodoxime Proxetil is a third generation semi-synthetic cephalosporin and a beta-lactam antibiotic with bactericidal activity. Cefpodoxime's effect is dependent on its binding to penicillin-binding proteins (PBPs) located in the bacterial cytoplasmic membrane. Binding results in the inhibition of the transpeptidase enzymes, thereby preventing cross-linking of the pentaglycine bridge with the fourth residue of the pentapeptide and interrupting consequent synthesis of peptidoglycan chains. As a result, cefpodoxime inhibits bacterial septum and cell wall synthesis formation.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-propan-2-yloxycarbonyloxyethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
    2.1.2 InChI
    InChI=1S/C21H27N5O9S2/c1-9(2)33-21(30)35-10(3)34-19(29)15-11(6-31-4)7-36-18-14(17(28)26(15)18)24-16(27)13(25-32-5)12-8-37-20(22)23-12/h8-10,14,18H,6-7H2,1-5H3,(H2,22,23)(H,24,27)/b25-13-/t10?,14-,18-/m1/s1
    2.1.3 InChI Key
    LTINZAODLRIQIX-FBXRGJNPSA-N
    2.1.4 Canonical SMILES
    CC(C)OC(=O)OC(C)OC(=O)C1=C(CSC2N1C(=O)C2NC(=O)C(=NOC)C3=CSC(=N3)N)COC
    2.1.5 Isomeric SMILES
    CC(C)OC(=O)OC(C)OC(=O)C1=C(CS[C@H]2N1C(=O)[C@H]2NC(=O)/C(=N\OC)/C3=CSC(=N3)N)COC
    2.2 Other Identifiers
    2.2.1 UNII
    2TB00A1Z7N
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-(isopropoxycarbonyloxy)ethyl-7-(2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetamido)-3-methoxymethyl-8-oxo-5-thia-1-azabicyclo(4,2,0)-oct-2-ene-2-carboxylate

    2. Cephalosporin 807

    3. Cs 807

    4. Cs-807

    5. Doxef

    6. U 76252

    7. U-76,252

    8. Vantin

    2.3.2 Depositor-Supplied Synonyms

    1. Vantin

    2. Banan

    3. 87239-81-4

    4. Orelox

    5. Doxef

    6. Cs-807

    7. Simplicef

    8. Otreon

    9. U-76252

    10. Podomexef

    11. Chebi:3505

    12. 2tb00a1z7n

    13. Cefodox

    14. Nsc-759161

    15. (rs)-1-((isopropoxycarbonyl)oxy)ethyl (+)-(6r,7r)-7-(2-(2-amino-4-thiazolyl)-2-((z)-methoxyimino)acetamido)-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

    16. Dsstox_cid_2766

    17. Dsstox_rid_76722

    18. Cefpodoxime 1-(isopropyloxycarbonyloxy)ethyl Ester

    19. Dsstox_gsid_22766

    20. Xtum-o

    21. 1-{[(propan-2-yloxy)carbonyl]oxy}ethyl (6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    22. 1-{[(propan-2-yloxy)carbonyl]oxy}ethyl 7beta-[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-(methoxymethyl)-3,4-didehydrocepham-4-carboxylate

    23. Cas-87239-81-4

    24. Simplicef [veterinary]

    25. Unii-2tb00a1z7n

    26. Orelox Paed

    27. Ncgc00164598-01

    28. Ncgc00183131-01

    29. Mfcd00865088

    30. Vantin (tn)

    31. Cefpodoxime Proxetil [usan:usp:jan]

    32. Schembl27071

    33. Mls001401428

    34. Chembl1201016

    35. Dtxsid1022766

    36. Cefpodoxime (as Proxetil)

    37. Cefpodoxime Proxetil (jp17/usp)

    38. Cefpodoxime Proxetil [jan]

    39. Hms3715j22

    40. Cefpodoxime Proxetil [usan]

    41. Cefpodoxime Proxetil, Vantin

    42. Hy-n7101

    43. Cefpodoxime Proxetil [vandf]

    44. Tox21_113377

    45. Tox21_113428

    46. Bdbm50248233

    47. Cefpodoxime Proxetil [mart.]

    48. S5350

    49. Cefpodoxime Proxetil [usp-rs]

    50. Cefpodoxime Proxetil [who-dd]

    51. Akos015994692

    52. Ccg-221250

    53. Ks-1149

    54. Nsc 759161

    55. Cefpodoxime Proxetil [green Book]

    56. (+-)-1-hydroxyethyl (+)-(6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate, 7(sup 2)-(z)-(o-methyloxime), Isopropyl Carbonate (ester)

    57. Cefpodoxime Proxetil [orange Book]

    58. Ru-51807

    59. Smr000469193

    60. Cefpodoxime Proxetil [ep Monograph]

    61. Cefpodoxime Proxetil [usp Impurity]

    62. Cefpodoxime Proxetil [usp Monograph]

    63. Cefpodoxime Proxetil For Peak Identification

    64. Cs-0027614

    65. C08115

    66. D00920

    67. Ab01209734-01

    68. 239c814

    69. A842048

    70. Cefpodoxime Proxetil For Impurity H Identification

    71. Cefpodoxime 1-(isopropoxycarbonyloxy)ethyl Ester

    72. Cefpodoxime 1-(isopropoxycarbonyloxy)ethyl Ester [mi]

    73. (+/-)-1-hydroxyethyl (+)-(6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate, 7 (sup 2)-(z)-(o-methyloxime), Isopropyl Carbonate (ester)

    74. (6r,7r)-1-((isopropoxycarbonyl)oxy)ethyl 7-((z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    75. (6r,7r)-7-(((2z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl)amino)-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid 1-(((1-methylethoxy)carbonyl)oxy)ethyl Ester

    76. 1-({[(1-methylethyl)oxy]carbonyl}oxy)ethyl (6r,7r)-7-({(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(methyloxy)imino]acetyl}amino)-3-[(methyloxy)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    77. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(methoxymethyl)-8-oxo-, 1-(((1-methylethoxy)carbonyl)oxy)ethyl Ester, (6r-(6.alpha.,7.beta.(z)))-

    78. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(methoxymethyl)-8-oxo-, 1-(((1-methylethoxy)carbonyl)oxy)ethyl Ester, (6r-(6alpha,7beta(z)))-

    79. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 7-[[(2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-(methoxymethyl)-8-oxo-, 1-[[(1-methylethoxy)carbonyl]oxy]ethyl Ester, (6r,7r)-

    2.4 Create Date
    2006-05-03
    3 Chemical and Physical Properties
    Molecular Weight 557.6 g/mol
    Molecular Formula C21H27N5O9S2
    XLogP30.6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count14
    Rotatable Bond Count13
    Exact Mass557.12501980 g/mol
    Monoisotopic Mass557.12501980 g/mol
    Topological Polar Surface Area235 Ų
    Heavy Atom Count37
    Formal Charge0
    Complexity976
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count1
    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.)

    4.2 FDA Pharmacological Classification
    4.2.1 Pharmacological Classes
    Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]