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    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
    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

    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 Weight 545.6 g/mol
    Molecular Formula C19H16N5NaO7S3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count13
    Rotatable Bond Count9
    Exact Mass545.01095567 g/mol
    Monoisotopic Mass545.01095567 g/mol
    Topological Polar Surface Area259 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity952
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    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

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    01-Jan-2021
    25-Oct-2024
    KGS
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    Average Price (USD/KGS)

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    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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