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    Ceftizoxima

    PharmaCompass
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    2D Structure
    Also known as: 68401-81-0, Ceftizoxima, Ceftizoximum, Cefizox, Ceftizoximum [inn-latin], Ceftizoxima [inn-spanish]
    Molecular Formula
    C13H13N5O5S2
    Molecular Weight
    383.4  g/mol
    InChI Key
    NNULBSISHYWZJU-LLKWHZGFSA-N
    FDA UNII
    C43C467DPE
    A semisynthetic cephalosporin antibiotic which can be administered intravenously or by suppository. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative organisms. It has few side effects and is reported to be safe and effective in aged patients and in patients with hematologic disorders.
    Ceftizoxime is a Cephalosporin Antibacterial.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C13H13N5O5S2/c1-23-17-7(5-4-25-13(14)15-5)9(19)16-8-10(20)18-6(12(21)22)2-3-24-11(8)18/h2,4,8,11H,3H2,1H3,(H2,14,15)(H,16,19)(H,21,22)/b17-7-/t8-,11-/m1/s1
    2.1.3 InChI Key
    NNULBSISHYWZJU-LLKWHZGFSA-N
    2.1.4 Canonical SMILES
    CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=CCS3)C(=O)O
    2.1.5 Isomeric SMILES
    CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=CCS3)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    C43C467DPE
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Cefizox

    2. Ceftizoxime Monosodium Salt

    3. Ceftizoxime Sodium

    4. Fk 749

    5. Fk-749

    6. Fk749

    7. Fr 13749

    8. Fr-13749

    9. Fr13749

    10. Monosodium Salt, Ceftizoxime

    11. Salt, Ceftizoxime Monosodium

    12. Sk And F 88373 2

    13. Sk And F 88373-2

    14. Sk And F 883732

    15. Skf 88373

    16. Skf-88373

    17. Skf88373

    18. Sodium, Ceftizoxime

    2.3.2 Depositor-Supplied Synonyms

    1. 68401-81-0

    2. Ceftizoxima

    3. Ceftizoximum

    4. Cefizox

    5. Ceftizoximum [inn-latin]

    6. Ceftizoxima [inn-spanish]

    7. Epocelin

    8. Fk-749

    9. Ceftizoxime (inn)

    10. Syn-7-(2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido)-3-cephem-4-carboxylic Acid

    11. C43c467dpe

    12. (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    13. Chebi:553473

    14. Ceftix

    15. Ceftizoxime [inn]

    16. Ceftizoxime [inn:ban]

    17. (6r,7r)-7-[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    18. Ceftisomin

    19. Unii-c43c467dpe

    20. (6r,7r)-7-(((2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

    21. Mfcd00072000

    22. (6r,7r)-7-(2-(2-amino-4-thiazolyl)-2z-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-2-carbonsaeure

    23. (6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxyamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-carbonsaeure-7-(z)-(o-methyloxim)

    24. Fr-13479

    25. Ceftizoxime [mi]

    26. Czx

    27. Ceftizoxime [jan]

    28. Chembl528

    29. Ceftizoxime [vandf]

    30. Schembl37504

    31. Ceftizoxime [usp-rs]

    32. Ceftizoxime [who-dd]

    33. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-8-oxo-, (6r-(6alpha,7beta(z)))-

    34. Dtxsid5022772

    35. Bdbm237182

    36. (6r,7r)-7-((z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    37. Hy-b1596

    38. Zinc3871970

    39. S4812

    40. Akos025310621

    41. Ccg-268439

    42. Db01332

    43. (6r,7r)-7-({(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(methyloxy)imino]acetyl}amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    44. (6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    45. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4- Thiazolyl)(methoxyimino)acetyl)amino)-8-oxo-, (6r-(6-alpha,7-beta(z)))-

    46. 7beta-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-2,3-didehydropenam-2-carboxylic Acid

    47. Cs-0013519

    48. C06890

    49. D07658

    50. 401c810

    51. A836131

    52. (6r,7r)-7-[[(2z)-2-(2-amino-4-thiazolyl)-2-methoxyimino-1-oxoethyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    53. (6r,7r)-7-[[(2z)-2-(2-azanyl-1,3-thiazol-4-yl)-2-methoxyimino-ethanoyl]amino]-8-oxidanylidene-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    54. (6r,7r)-7-[[(2z)-2-(2-imino-3h-thiazol-4-yl)-2-methoxyimino-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    55. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 7-[[(2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-, (6r,7r)-

    2.4 Create Date
    2006-05-04
    3 Chemical and Physical Properties
    Molecular Weight 383.4 g/mol
    Molecular Formula C13H13N5O5S2
    XLogP30
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count5
    Exact Mass383.03581088 g/mol
    Monoisotopic Mass383.03581088 g/mol
    Topological Polar Surface Area201 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity669
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Cetizoxime was previously indicated for the treatment of infections due to susceptible strains of bacteria.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Ceftizoxime is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative organisms. It has few side effects and is reported to be safe and effective in aged patients and in patients with hematologic disorders.

    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 FDA Pharmacological Classification
    5.3.1 Active Moiety
    CEFTIZOXIME
    5.3.2 FDA UNII
    C43C467DPE
    5.3.3 Pharmacological Classes
    Chemical Structure [CS] - Cephalosporins
    5.4 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01D - Other beta-lactam antibacterials

    J01DD - Third-generation cephalosporins

    J01DD07 - Ceftizoxime

    5.5 Absorption, Distribution and Excretion

    Route of Elimination

    Excreted virtually unchanged by the kidneys in 24 hours.

    Volume of Distribution

    The mean apparent volume of distribution ranges between 15 - 28L.

    5.6 Metabolism/Metabolites

    Ceftizoxime is not metabolized and is excreted virtually unchanged by the kidneys in 24 hours.

    5.7 Mechanism of Action

    Ceftizoxime is an aminothiazolyl cephalosporin with an extended spectrum of activity against many gram-negative, nosocomially acquired pathogens. It has excellent beta-lactamase stability, with good in vitro activity against Haemophilus influenzae, Neisseria gonorrhoeae and Klebsiella pneumoniae. Ceftizoxime, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits 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 ceftizoxime interferes with an autolysin inhibitor.