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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 HCl
    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 Weight 560.0 g/mol
    Molecular Formula C19H18ClN5O7S3
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count13
    Rotatable Bond Count9
    Exact Mass559.0056891 g/mol
    Monoisotopic Mass559.0056891 g/mol
    Topological Polar Surface Area256 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity945
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Pharmacology and Biochemistry
    4.1 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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