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    Faropenem Medoxomil

    ACTIVE PHARMA INGREDIENTS

    DIGITAL CONTENT

    MARKET PLACE

    PharmaCompass
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    2D Structure
    Also known as: 141702-36-5, Faropenem medoxomil, Faropenem medoxil, Sun-a0026, Fropenem daloxate, Faropenem medoxomil [usan]
    Molecular Formula
    C17H19NO8S
    Molecular Weight
    397.4  g/mol
    InChI Key
    JQBKWZPHJOEQAO-DVPVEWDBSA-N
    FDA UNII
    5OK523O4FU
    Faropenem Medoxomil is a daloxate ester prodrug form of faropenem, a penem with a tetrahydrofuran substituent at position C2, with broad-spectrum antibacterial activity against many gram-positive and gram-negative aerobes and anaerobes. Faropenem medoxomil is hydrolyzed in vivo to release the active free acid. Compared with imipenem, faropenem has improved chemical stability and reduced central nervous system effects. In addition, faropenem is resistant to hydrolysis by many beta-lactamases.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
    2.1.2 InChI
    InChI=1S/C17H19NO8S/c1-7(19)11-14(20)18-12(13(27-15(11)18)9-4-3-5-23-9)16(21)24-6-10-8(2)25-17(22)26-10/h7,9,11,15,19H,3-6H2,1-2H3/t7-,9-,11+,15-/m1/s1
    2.1.3 InChI Key
    JQBKWZPHJOEQAO-DVPVEWDBSA-N
    2.1.4 Canonical SMILES
    CC1=C(OC(=O)O1)COC(=O)C2=C(SC3N2C(=O)C3C(C)O)C4CCCO4
    2.1.5 Isomeric SMILES
    CC1=C(OC(=O)O1)COC(=O)C2=C(S[C@H]3N2C(=O)[C@@H]3[C@@H](C)O)[C@H]4CCCO4
    2.2 Other Identifiers
    2.2.1 UNII
    5OK523O4FU
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. A0026

    2. Bay 56-6854

    3. Bay 566854

    4. Bay-56-6854

    5. Bay-566854

    6. Bay56-6854

    7. Bay566854

    8. Faropenem Medoxomil

    9. Sun 208

    10. Sun A0026

    11. Sun-208

    12. Sun-a0026

    13. Sun208

    2.3.2 Depositor-Supplied Synonyms

    1. 141702-36-5

    2. Faropenem Medoxomil

    3. Faropenem Medoxil

    4. Sun-a0026

    5. Fropenem Daloxate

    6. Faropenem Medoxomil [usan]

    7. Bay-56-6854

    8. A-0026

    9. 5ok523o4fu

    10. (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    11. A0026

    12. Sun-208

    13. Faropenem Medoxomil (usan)

    14. Orapem

    15. 4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid, 6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-tetrahydro-2-furanyl]-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester, (5r,6s)-

    16. Unii-5ok523o4fu

    17. Faropenem-medoxomil

    18. Bay 566854

    19. Bay 56-6854

    20. A 0026

    21. Schembl2334640

    22. Sun208

    23. Faropenem Daloxate [mi]

    24. Chembl1257070

    25. Sun A0026

    26. Sun 208

    27. Chebi:134710

    28. Zinc3806644

    29. Bay566854

    30. Bay-566854

    31. Bay56-6854

    32. Cs-0390

    33. Db05659

    34. Hy-10004

    35. D08919

    36. 702f365

    37. A911194

    38. Q27095691

    39. (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (5r,6s)-6-((1r)-1-hydroxyethyl)-7-oxo-3-((2r)-tetrahydrofuran-2-yl)-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylate

    40. (5-methyl-2-oxo-1,3-dioxoren-4-yl)methyl(5r,6s)-6-((r)-1-hydroxyethyl)-7-oxo-3-((r)-2-tetrahydrofuryl)-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylate

    41. (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-oxolane-2-yl]-4-thia-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic Acid 5-methyl-2-oxo-1,3-dioxole-4-ylmethyl Ester

    42. 4-thia-1-azabicyclo(.32.0)hept-2-ene-2-carboxylic Acid, 6-((1r)-1-hydroxyethyl)-7-oxo-3-((2r)-tetrahydro-2-furanyl)-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester, (5r,6s)-

    43. 4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-((1r)-1-hydroxyethyl)-7-oxo-3-((2r)-tetrahydro-2-furanyl)-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester, (5r,6s)

    44. 4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furanyl)-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester, (5r-(3(r*),5alpha,6alpha(r*)))-

    45. 4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid, 6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-tetrahydro-2-furanyl]-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester

    2.4 Create Date
    2006-07-28
    3 Chemical and Physical Properties
    Molecular Weight 397.4 g/mol
    Molecular Formula C17H19NO8S
    XLogP30.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count6
    Exact Mass397.08313774 g/mol
    Monoisotopic Mass397.08313774 g/mol
    Topological Polar Surface Area137 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity775
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in bacterial infection, bronchitis, otitis media, and pediatric indications.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Faropenem has demonstrated excellent in vitro activity against common respiratory pathogens, many aerobic gram-positive organisms, and anaerobes. Activity against gram-negative organisms is more reserved. In vivo data suggest that faropenem is efficacious in treating community-acquired infections including uncomplicated skin and skin structure infections; however, more data may help to characterize faropenem's place in antimicrobial therapy.

    5.2 Mechanism of Action

    Like other beta-lactam antibiotics, faropenem acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria. It does this by binding to and competitively inhibiting the transpeptidase enzyme used by bacteria to cross-link the peptide (D-alanyl-alanine) used in peptidogylcan synthesis.