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    Sulopenem Etzadroxil

    DEVELOPMENTS

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    PATENTS & EXCLUSIVITIES

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    2D Structure
    Also known as: 1000296-70-7, 2-ethylbutanoyloxymethyl (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(1r,3s)-1-oxothiolan-3-yl]sulfanyl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate, Sulopenem etzadroxil (usan), Sulopenem etzadroxil [usan], Pf-03709270, 492m3i304t
    Molecular Formula
    C19H27NO7S3
    Molecular Weight
    477.6  g/mol
    InChI Key
    NBPVNGWRLGHULH-CSOWVJSESA-N
    FDA UNII
    492M3I304T
    Sulopenem Etzadroxil is an orally available ester prodrug form of sulopenem, a thiopenem with broad-spectrum antibacterial activity against most gram-positive and gram-negative bacteria. After oral administration of sulopenem etzadroxil, the ester bond is cleaved, releasing active sulopenem. Sulopenem is not active against Pseudomonas aeruginosa. In addition, this agent is fairly stable against hydrolysis by various beta-lactamases.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-ethylbutanoyloxymethyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(1R,3S)-1-oxothiolan-3-yl]sulfanyl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
    2.1.2 InChI
    InChI=1S/C19H27NO7S3/c1-4-11(5-2)17(23)26-9-27-18(24)14-19(28-12-6-7-30(25)8-12)29-16-13(10(3)21)15(22)20(14)16/h10-13,16,21H,4-9H2,1-3H3/t10-,12+,13+,16-,30-/m1/s1
    2.1.3 InChI Key
    NBPVNGWRLGHULH-CSOWVJSESA-N
    2.1.4 Canonical SMILES
    CCC(CC)C(=O)OCOC(=O)C1=C(SC2N1C(=O)C2C(C)O)SC3CCS(=O)C3
    2.1.5 Isomeric SMILES
    CCC(CC)C(=O)OCOC(=O)C1=C(S[C@H]2N1C(=O)[C@@H]2[C@@H](C)O)S[C@H]3CC[S@@](=O)C3
    2.2 Other Identifiers
    2.2.1 UNII
    492M3I304T
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 1000296-70-7

    2. 2-ethylbutanoyloxymethyl (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(1r,3s)-1-oxothiolan-3-yl]sulfanyl-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    3. Sulopenem Etzadroxil (usan)

    4. Sulopenem Etzadroxil [usan]

    5. Pf-03709270

    6. 492m3i304t

    7. Sulopenem-etzadroxil

    8. Pf 03709270

    9. Schembl3412832

    10. Dtxsid80635293

    11. 4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-((1r)-1-hydroxyethyl)-7-oxo-3-(((1r,3s)-tetrahydro-1-oxido-3-thienyl)thio)-, (2-ethyl-1-oxobutoxy)methyl Ester, (5r,6s)-

    12. Ex-a3685

    13. Pf 03709270 (ulopenem Etzadroxil)

    14. Ac-33246

    15. Hy-109754

    16. Cs-0033925

    17. D09672

    18. Q27259210

    19. (2-ethyl-1-oxobutoxy)methyl (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[[(1r,3s)-tetrahydro-1-oxido-3-thienyl]thio]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    20. (2-ethyl-1-oxobutoxy)methyl (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[[(1r,3s)-tetrahydro-1-oxido-3-thienyl]thio]-4thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    21. Methylene 2-ethylbutanoate (5r,6s)-6-((1r)-1-hydroxyethyl)-7-oxo-3-(((1r,3s)-1-oxotetrahydro-1h-1.lamba.(sup 4)-thiophen-3-yl)sulfanyl)-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylate

    2.4 Create Date
    2008-01-14
    3 Chemical and Physical Properties
    Molecular Weight 477.6 g/mol
    Molecular Formula C19H27NO7S3
    XLogP32.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count11
    Exact Mass477.09496572 g/mol
    Monoisotopic Mass477.09496572 g/mol
    Topological Polar Surface Area180 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity767
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1