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    CAS 135821-54-4

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    CAS 135821-54-4
    Also known as: Ceftizoxime alapivoxil, 135821-54-4, Ceftizoxime alapivoxil [inn], 3mm3320ljn, As-924, Unii-3mm3320ljn
    Molecular Formula
    C22H28N6O8S2
    Molecular Weight
    568.6  g/mol
    InChI Key
    VOPANQNVVCPHQR-IVVGYLHBSA-N
    FDA UNII
    3MM3320LJN
    Ceftizoxime Alapivoxil is the alapivalate ester prodrug form of ceftizoxime, a semi-synthetic, broad-spectrum, beta-lactamase-resistant, third-generation cephalosporin with antibacterial activity. After oral administration of ceftizoxime alapivoxil, the ester bond is cleaved, releasing active ceftizoxime.
    1 2D Structure

    CAS 135821-54-4

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(2Z)-2-[2-[[(2S)-2-aminopropanoyl]amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
    2.1.2 InChI
    InChI=1S/C22H28N6O8S2/c1-10(23)15(29)26-21-24-11(8-38-21)13(27-34-5)16(30)25-14-17(31)28-12(6-7-37-18(14)28)19(32)35-9-36-20(33)22(2,3)4/h6,8,10,14,18H,7,9,23H2,1-5H3,(H,25,30)(H,24,26,29)/b27-13-/t10-,14+,18+/m0/s1
    2.1.3 InChI Key
    VOPANQNVVCPHQR-IVVGYLHBSA-N
    2.1.4 Canonical SMILES
    CC(C(=O)NC1=NC(=CS1)C(=NOC)C(=O)NC2C3N(C2=O)C(=CCS3)C(=O)OCOC(=O)C(C)(C)C)N
    2.1.5 Isomeric SMILES
    C[C@@H](C(=O)NC1=NC(=CS1)/C(=N/OC)/C(=O)N[C@H]2[C@@H]3N(C2=O)C(=CCS3)C(=O)OCOC(=O)C(C)(C)C)N
    2.2 Other Identifiers
    2.2.1 UNII
    3MM3320LJN
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (2-(2-alanylaminothiazol-4-yl)-2-methoxyiminoacetamido)-3-cephem-4-carboxylate

    2. As 924

    3. As-924

    4. Ceftizoxime Alapivoxil

    2.3.2 Depositor-Supplied Synonyms

    1. Ceftizoxime Alapivoxil

    2. 135821-54-4

    3. Ceftizoxime Alapivoxil [inn]

    4. 3mm3320ljn

    5. As-924

    6. Unii-3mm3320ljn

    7. Chembl2106058

    8. Zinc59660352

    9. C21592

    10. (2-(2-alanylaminothiazol-4-yl)-2-methoxyiminoacetamido)-3-cephem-4-carboxylate

    11. (+)-(pivaloyloxy)methyl (6r,7r)-7-(2-(2-(l-alanylamino)thiazol-4-yl)glyoxylamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate 7(sup 2)-(z)-(o)-methyloxime)

    12. (+)-(pivaloyloxy)methyl (6r,7r)-7-(2-(2-(l-alanylamino)thiazol-4-yl)glyoxylamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate 7,2-(z)-(o)-methyloxime)

    13. (+)-(pivaloyloxy)methyl (6r,7r)-7-(2-(2-(l-alanylamino)thiazol-4-yl)glyoxylamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate 72-(z)-(o)-methyloxime)

    14. (7r)-7-[2-[2-[[(2s)-2-aminopropionyl]amino]thiazole-4-yl]-2-(methoxyimino)acetylamino]cepham-3-ene-4-carboxylic Acid (pivaloyloxy)methyl Ester

    2.4 Create Date
    2006-10-24
    3 Chemical and Physical Properties
    Molecular Weight 568.6 g/mol
    Molecular Formula C22H28N6O8S2
    XLogP31.1
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count13
    Rotatable Bond Count12
    Exact Mass568.14100422 g/mol
    Monoisotopic Mass568.14100422 g/mol
    Topological Polar Surface Area245 Ų
    Heavy Atom Count38
    Formal Charge0
    Complexity1050
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
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