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Also known as: 103980-44-5, Ceftiofur hcl, Ceftiofur, hcl, Ceftiofur hydrochloride [usan], Ceftiofur (hydrochloride), Ceftiofur monohydrochloride

Molecular Formula

C₁₉H₁₈ClN₅O₇S₃

Molecular Weight

560.0 g/mol

InChI Key

KEQFDTJEEQKVLM-JUODUXDSSA-N

FDA UNII

6822A07436

Ceftiofur Hydrochloride is the hydrochloride 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 HCl

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]-3-(furan-2-carbonylsulfanylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrochloride

2.1.2 InChI

InChI=1S/C19H17N5O7S3.ClH/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);1H/b23-11-;/t12-,16-;/m1./s1

2.1.3 InChI Key

KEQFDTJEEQKVLM-JUODUXDSSA-N

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.Cl

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.Cl

2.2 Other Identifiers

2.2.1 UNII

6822A07436

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ceftiofur

2. Ceftiofur Sodium

3. Naxcel

4. U 64279a

5. U-64279e

2.3.2 Depositor-Supplied Synonyms

1. 103980-44-5

2. Ceftiofur Hcl

3. Ceftiofur, Hcl

4. Ceftiofur Hydrochloride [usan]

5. Ceftiofur (hydrochloride)

6. Ceftiofur Monohydrochloride

7. (6r,7r)-7-((z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-(((furan-2-carbonyl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Hydrochloride

8. U-64279a

9. Nsc-759845

10. (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-carboxylic Acid;hydrochloride

11. Ceftiofur Hydrochloride 100 Microg/ml In Methanol

12. 6822a07436

13. Ceftiofur Hydrochloride (usan)

14. (6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-3-(mercaptomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7(sup 2)-(z)-(o-methyloxime), 2-furoate (ester), Monohydrochloride

15. Excede

16. Excenel Hydrochloride

17. Unii-6822a07436

18. U 64279a

19. U 67279a

20. U-67279a

21. Schembl203568

22. Chembl2106486

23. Dtxsid101034300

24. Ex-a1380

25. Hy-b0026

26. Mfcd04038020

27. Akos015920153

28. Akos037653220

29. Ceftiofur Hydrochloride [mart.]

30. Cs-w019858

31. Gs-3560

32. Nsc 759845

33. Ceftiofur Hydrochloride [usp-rs]

34. Ceftiofur Monohydrochloride [mi]

35. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,7-[[(2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[(2-furanylcarbonyl)thio]methyl]-8-oxo-, Monohydrochloride, (6r,7r)-

36. Ceftiofur Hydrochloride [green Book]

37. Ceftiofur Hydrochloride [usp Monograph]

38. D03430

39. 980c445

40. J-001081

41. J-523051

42. Ceftiofur Hydrochloride, Vetranal(tm), Analytical Standard

43. Ceftiofur Hydrochloride, United States Pharmacopeia (usp) Reference Standard

44. N-(4-cyano-3-(trifluoromethyl)phenyl)-3-(4-fluorophenylsulfonyl)-2,2-dimethylpropanamide

45. (6r,7r)-3-[(furan-2-carbonylsulfanyl)methyl]-7-{[(2z)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Hydrochloride

46. 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-, Monohydrochloride, (6r-(6.alpha.,7.beta.(z)))-

47. 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-, Monohydrochloride, (6r-(6alpha,7beta(z)))-

48. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(((2-furanylcarbonyl)thio)methyl)-8-oxo, Monohydrochloride, (6r,7r)

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₈ClN₅O₇S₃
Molecular Weight	560.0 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	9
Exact Mass	559.0056891 g/mol
Monoisotopic Mass	559.0056891 g/mol
Topological Polar Surface Area	256 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	945
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