Ceftiofur sodium salt

Synopsis, Chemistry

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Also known as: 104010-37-9, Ceftiofur sodium salt, Ceftiofur monosodium salt, Sodium ceftiofur, Naxcel, Ceftiofur sodium [usan]

Molecular Formula

C₁₉H₁₆N₅NaO₇S₃

Molecular Weight

545.6 g/mol

InChI Key

RFLHUYUQCKHUKS-JUODUXDSSA-M

FDA UNII

NHI34IS56E

Ceftiofur Sodium is the sodium salt form of ceftiofur, a semisynthetic, beta-lactamase-stable, broad-spectrum, third-generation cephalosporin with antibacterial activity. Ceftiofur binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.

1 2D Structure

Ceftiofur sodium salt

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(furan-2-carbonylsulfanylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

2.1.2 InChI

InChI=1S/C19H17N5O7S3.Na/c1-30-23-11(9-7-34-19(20)21-9)14(25)22-12-15(26)24-13(17(27)28)8(5-32-16(12)24)6-33-18(29)10-3-2-4-31-10;/h2-4,7,12,16H,5-6H2,1H3,(H2,20,21)(H,22,25)(H,27,28);/q;+1/p-1/b23-11-;/t12-,16-;/m1./s1

2.1.3 InChI Key

RFLHUYUQCKHUKS-JUODUXDSSA-M

2.1.4 Canonical SMILES

CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)CSC(=O)C4=CC=CO4)C(=O)[O-].[Na+]

2.1.5 Isomeric SMILES

CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)CSC(=O)C4=CC=CO4)C(=O)[O-].[Na+]

2.2 Other Identifiers

2.2.1 UNII

NHI34IS56E

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ceftiofur

2. Ceftiofur Hydrochloride

3. Naxcel

4. U 64279a

5. U-64279e

2.3.2 Depositor-Supplied Synonyms

1. 104010-37-9

2. Ceftiofur Sodium Salt

3. Ceftiofur Monosodium Salt

4. Sodium Ceftiofur

5. Naxcel

6. Ceftiofur Sodium [usan]

7. Ceftiofur (sodium)

8. U-64279e

9. Ccris 7601

10. Ceftiofur Natrium

11. Cm 31-916

12. Nhi34is56e

13. Chebi:31383

14. Ceftiofurum

15. Cm-31-916

16. Sodium;(6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(furan-2-carbonylsulfanylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

17. Unii-nhi34is56e

18. Ceftiofur Sodium (tn)

19. Sodium (6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-3-(mercaptomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate, 7(sup 2)-(z)-(o-methyloxime), 2-furoate (ester)

20. Ceftiofur Sodium (jan/usan)

21. Ceftiofur Sodium [jan]

22. Schembl2369906

23. Chembl2105998

24. Ceftiofur Sodium [mart.]

25. Dtxsid30891706

26. Ceftiofur Natrium [who-dd]

27. Hy-b0898

28. Mfcd01766184

29. Ceftiofur Sodium [green Book]

30. Akos015998604

31. Ceftiofur Monosodium Salt [mi]

32. Ks-1164

33. Ceftiofur Sodium [usp Monograph]

34. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(((2-furanylcarbonyl)thio)methyl)-8-oxo-, Monosodium Salt, (6r-(6alpha,7beta(z)))-

35. D01682

36. (6r,7r)-7-[[(2z)-2-(2-aminothiazol-4-yl)-2-methoxyimino-acetyl]amino]-3-(furan-2-carbonylsulfanylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

37. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(((2-furanylcarbonyl)thio)methyl)-8-oxo-, Monosodium Salt, (6r-(6.alpha.,7.beta.(z)))-

38. Sodium (6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-3-(mercaptomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate, 72-(z)-(o-methyloxime), 2-furoate (ester)

39. Sodium (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(furan-2-carbonylsulfanylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₆N₅NaO₇S₃
Molecular Weight	545.6 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	9
Exact Mass	545.01095567 g/mol
Monoisotopic Mass	545.01095567 g/mol
Topological Polar Surface Area	259 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	952
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	2

4 Drug and Medication Information

4.1 Drug Indication

* Pigs:

- Treatment of bacterial respiratory disease associated with Actinobacillus pleuropneumoniae, Pasteurella multocida, Haemophilus parasuis and Streptococcus suis.

- Treatment of septicaemia, polyarthritis or polyserositis associated with Streptococcus suis infection.

* Cattle:

- Treatment of acute interdigital necrobacillosis in cattle also known as Panaritium or foot rot.

- Treatment of acute post-partum (puerperal) metritis in cattle, in cases where treatment with another antimicrobial has failed.

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.)

5.2 ATC Code

QJ01DD90