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Ceftizoxima

Polpharma is a Polish CDMO of APIs and a significant European API producer, delivering products to companies worldwide.

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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

Ceftizoxima

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 Formula	C₁₃H₁₃N₅O₅S₂
Molecular Weight	383.4 g/mol
XLogP3	0
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	5
Exact Mass	383.03581088 g/mol
Monoisotopic Mass	383.03581088 g/mol
Topological Polar Surface Area	201 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	669
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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