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    Chemistry

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    Also known as: Spectracef, 117467-28-4, Cefditoren pivaloyloxymethyl ester, Cdtr-pi, Meiact, Cefditoren (pivoxil)
    Molecular Formula
    C25H28N6O7S3
    Molecular Weight
    620.7  g/mol
    InChI Key
    AFZFFLVORLEPPO-UVYJNCLZSA-N
    FDA UNII
    78THA212DH
    Cefditoren Pivoxil
    Cefditoren Pivoxil is a semi-synthetic, broad-spectrum, beta-lactamase resistant, third-generation cephalosporin antibiotic with bactericidal activity. Cefditoren pivoxil is a prodrug that is rapidly hydrolyzed by intestinal esterases during absorption to the microbiologically active cefditoren, an active aminothiazolyl cephalosporin. Cefditoren inactivates penicillin binding proteins (PBPs) thereby interfering with peptidoglycan synthesis and inhibiting bacterial cell wall synthesis. Another consequence of beta-lactam exposure results in the loss of lipoteichoic acids from the cell wall. Lipoteichoic acids inhibit murein hydrolase activity and their absence from the cell wall triggers uncontrolled autolytic activity rendering bacterial cells susceptible to osmotic shock. This results in a reduction of cell wall stability and causes cell lysis.
    1 2D Structure

    Cefditoren Pivoxil

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
    2.1.2 InChI
    InChI=1S/C25H28N6O7S3/c1-12-15(41-10-27-12)7-6-13-8-39-21-17(29-19(32)16(30-36-5)14-9-40-24(26)28-14)20(33)31(21)18(13)22(34)37-11-38-23(35)25(2,3)4/h6-7,9-10,17,21H,8,11H2,1-5H3,(H2,26,28)(H,29,32)/b7-6-,30-16-/t17-,21-/m1/s1
    2.1.3 InChI Key
    AFZFFLVORLEPPO-UVYJNCLZSA-N
    2.1.4 Canonical SMILES
    CC1=C(SC=N1)C=CC2=C(N3C(C(C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)OCOC(=O)C(C)(C)C
    2.1.5 Isomeric SMILES
    CC1=C(SC=N1)/C=C\C2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)SC2)C(=O)OCOC(=O)C(C)(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    78THA212DH
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (-)-(6r,7r)-2,2-dimethylpropionyloxymethyl 7-((z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido)-3-((z)-2-(4-methylthiazol-5-yl)ethenyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

    2. 7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-(2-(4-methylthiazol-5-yl)ethenyl)cephem-4-carboxylic Acid Pivaloyloxymethyl Ester

    3. Cdtr-pi

    4. Me 1207

    5. Me-1207

    6. Spectracef

    2.3.2 Depositor-Supplied Synonyms

    1. Spectracef

    2. 117467-28-4

    3. Cefditoren Pivaloyloxymethyl Ester

    4. Cdtr-pi

    5. Meiact

    6. Cefditoren (pivoxil)

    7. Cefditoren Pivoxil [jan]

    8. Me-1207

    9. Cefditorin Pivoxil

    10. Me1207

    11. Cefditoren Pivoxil Hcl

    12. 78tha212dh

    13. Cefditorin

    14. Chebi:560555

    15. Me 1207

    16. Nsc-759098

    17. 2,2-dimethylpropanoyloxymethyl (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    18. Cefditoren Pi Voxil

    19. Cefditoren-pivoxil

    20. [(2,2-dimethylpropanoyl)oxy]methyl (6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    21. [(2,2-dimethylpropanoyl)oxy]methyl 7beta-(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido-3-[(z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-3,4-didehydrocepham-4-carboxylic Acid

    22. 1448435-17-3

    23. Pivaloyloxymethyl (+)-(6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    24. Ccris 7768

    25. Unii-78tha212dh

    26. Spectracef (tn)

    27. Ncgc00095175-01

    28. Meiact (tn)

    29. Mfcd00933166

    30. Dsstox_cid_28669

    31. Dsstox_rid_82939

    32. Dsstox_gsid_48743

    33. Schembl182876

    34. Chembl454446

    35. Cefditoren Pivoxil [usan:jan]

    36. Dtxsid2048743

    37. Cefditoren Pivoxil [usan]

    38. Cefditoren Pivoxil (jp17/usan)

    39. Cefditoren Pivoxil [vandf]

    40. Cefditoren Pivoxil [mart.]

    41. Cefditoren Pivoxil [who-dd]

    42. Tox21_113197

    43. Hy-17452a

    44. S1768

    45. Akos025311444

    46. Ccg-270254

    47. Cs-1949

    48. Nsc 759098

    49. Cefditoren Pivoxil [orange Book]

    50. Ncgc00095175-08

    51. (pivaloyloxy)methyl (6r,7r)-7-((z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-((z)-2-(4-methylthiazol-5-yl)vinyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    52. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-((1z)-2-(4-methyl-5-thiazolyl)ethenyl)-8-oxo-,2,2-dimethyl-1-oxopropoxy)methyl Ester, (6r,7r)-

    53. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(2-(4-methyl-5-thiazolyl)ethenyl)-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (6r-(3(z),6-alpha,7-beta-(z)))-

    54. As-12951

    55. B2086

    56. Cas-117467-28-4

    57. Cefditoren Pivaloyloxymethyl Ester [mi]

    58. D01628

    59. Ab01274730-01

    60. Ab01274730_02

    61. 467c284

    62. Brd-k72167406-001-03-9

    63. (+)-(6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-3-((z)-2-(4-methyl-5-thiazolyl)vinyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate Pivaloyloxy Methyl Ester, 7(sup 2)-(z)-(o-methyloxime)

    64. (6r,7r)-(pivaloyloxy)methyl 7-((z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-((z)-2-(4-methylthiazol-5-yl)vinyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    65. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7(((2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-((1z)-2-(4-methyl-5-thiazolyl)ethenyl)-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (6r,7r)-

    2.4 Create Date
    2006-04-28
    3 Chemical and Physical Properties
    Molecular Weight 620.7 g/mol
    Molecular Formula C25H28N6O7S3
    XLogP34.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count14
    Rotatable Bond Count12
    Exact Mass620.11816077 g/mol
    Monoisotopic Mass620.11816077 g/mol
    Topological Polar Surface Area257 Ų
    Heavy Atom Count41
    Formal Charge0
    Complexity1160
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count2
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameSpectracef
    PubMed HealthCefditoren Pivoxil (By mouth)
    Drug ClassesAntibiotic
    Drug LabelSPECTRACEF tablets contain cefditoren pivoxil, a semi-synthetic cephalosporin antibiotic for oral administration. It is a prodrug which is hydrolyzed by esterases during absorption, and the drug is distributed in the circulating blood as active cef...
    Active IngredientCefditoren pivoxil
    Dosage FormTablet
    RouteOral
    Strength200mg; 400mg
    Market StatusPrescription
    CompanyVansen Pharma

    2 of 2  
    Drug NameSpectracef
    PubMed HealthCefditoren Pivoxil (By mouth)
    Drug ClassesAntibiotic
    Drug LabelSPECTRACEF tablets contain cefditoren pivoxil, a semi-synthetic cephalosporin antibiotic for oral administration. It is a prodrug which is hydrolyzed by esterases during absorption, and the drug is distributed in the circulating blood as active cef...
    Active IngredientCefditoren pivoxil
    Dosage FormTablet
    RouteOral
    Strength200mg; 400mg
    Market StatusPrescription
    CompanyVansen Pharma

    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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    11-Jan-2021
    16-Oct-2024
    KGS
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