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    Tebipenem Pivoxil

    ACTIVE PHARMA INGREDIENTS

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    PharmaCompass
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    2D Structure
    Also known as: 161715-24-8, Orapenem, Tbpm-pi, Me1211, L-084, Ljc 11,084
    Molecular Formula
    C22H31N3O6S2
    Molecular Weight
    497.6  g/mol
    InChI Key
    SNUDIPVBUUXCDG-QHSBEEBCSA-N
    FDA UNII
    95AK1A52I8
    Tebipenem Pivoxil is an orally available pivaloyloxymethyl ester prodrug of tebipenem, a broad-spectrum 1-beta-methylcarbapenem antibiotic with a 1-(1,3-thiazolin-2-yl) azetidin-3-ylthio group at the C-2 position. After oral administration of tebipenem pivoxil, the ester bond is cleaved, releasing active tebipenem.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2,2-dimethylpropanoyloxymethyl (4R,5S,6S)-3-[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
    2.1.2 InChI
    InChI=1S/C22H31N3O6S2/c1-11-15-14(12(2)26)18(27)25(15)16(19(28)30-10-31-20(29)22(3,4)5)17(11)33-13-8-24(9-13)21-23-6-7-32-21/h11-15,26H,6-10H2,1-5H3/t11-,12-,14-,15-/m1/s1
    2.1.3 InChI Key
    SNUDIPVBUUXCDG-QHSBEEBCSA-N
    2.1.4 Canonical SMILES
    CC1C2C(C(=O)N2C(=C1SC3CN(C3)C4=NCCS4)C(=O)OCOC(=O)C(C)(C)C)C(C)O
    2.1.5 Isomeric SMILES
    C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1SC3CN(C3)C4=NCCS4)C(=O)OCOC(=O)C(C)(C)C)[C@@H](C)O
    2.2 Other Identifiers
    2.2.1 UNII
    95AK1A52I8
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. L 084

    2. L-084

    2.3.2 Depositor-Supplied Synonyms

    1. 161715-24-8

    2. Orapenem

    3. Tbpm-pi

    4. Me1211

    5. L-084

    6. Ljc 11,084

    7. 2,2-dimethylpropanoyloxymethyl (4r,5s,6s)-3-[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    8. Ljc-11084

    9. Me-1211

    10. 95ak1a52i8

    11. Tebipenempivoxil

    12. Tebipenem [inn]

    13. (4r,5s,6s)-(pivaloyloxy)methyl 3-((1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl)thio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    14. (1r,5s,6s)-6-[1(r)-hydroxyethyl]-1-methyl-2-[1-(2-thiazolin-2-yl)azetidin-3-ylsulfanyl]-1-carba-2-penem-3-carboxylic Acid Pivaloyloxymethyl Ester

    15. Tebipenem Pivoxil (l-084)

    16. Tebipenem Pivoxil [inn]

    17. Tebipenem Pivoxil(l-084)

    18. Unii-95ak1a52i8

    19. Orapenem (tn)

    20. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 3-((1-(4,5-dihydro-2-thiazolyl)-3-azetidinyl)thio)-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (4r,5s,6s)-

    21. 1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid, 3-[[1-(4,5-dihydro-2-thiazolyl)-3-azetidinyl]thio]-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (4r,5s,6s)-

    22. Mls006011128

    23. Schembl305541

    24. Tebipenem Pivoxil [mi]

    25. Tebipenem Pivoxil [usan:inn]

    26. Tebipenem Pivoxil [jan]

    27. Chembl2107486

    28. Tebipenem Pivoxil [usan]

    29. Gtpl10864

    30. Dtxsid00167228

    31. Chebi:135799

    32. Tebipenem Pivoxil [who-dd]

    33. Ex-a1256

    34. Hy-b0396

    35. Who 7924

    36. Zinc4217736

    37. Tebipenem Pivoxil (jan/usan/inn)

    38. Ljc 11084

    39. Mfcd17215369

    40. S2159

    41. Akos015899532

    42. Ccg-269673

    43. Ljc-11,084

    44. Ncgc00346570-01

    45. Ncgc00346570-04

    46. (pivaloyloxy)methyl (4r,5s,6s)-3-((1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl)thio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    47. [(4r,5s,6s)-3-{[1-(4,5-dihydro-1,3-thiazol-2-yl)azetidin-3-yl]sulfanyl}-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carbonyloxy]methyl 2,2-dimethylpropanoate

    48. Ac-22712

    49. As-75334

    50. L-084;me1211

    51. Smr004702908

    52. L 084

    53. C73086

    54. D09598

    55. Ab01566835_01

    56. A854567

    57. Q1623593

    58. ((2,2-dimethylpropanoyl)oxy)methyl (4r,5s,6s)-3-((1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl)sulfanyl)-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylate

    59. (4r,5r,6s)-3-((1-(4,5-dihydro-2-thiazolyl)-3-azetidinyl)thio)-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid (2,2-dimethyl-1-oxopropoxy) Methyl Ester

    60. (4r,5s,6s)-(pivaloyloxy)methyl3-((1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl)thio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    61. 2,2-dimethylpropanoyloxymethyl (4r,5s,6s)-3-[1-(4,5-dihydrothiazol-2-yl)azetidin-3-yl]sulfanyl-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    2.4 Create Date
    2006-10-25
    3 Chemical and Physical Properties
    Molecular Weight 497.6 g/mol
    Molecular Formula C22H31N3O6S2
    XLogP32.3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count10
    Exact Mass497.16542806 g/mol
    Monoisotopic Mass497.16542806 g/mol
    Topological Polar Surface Area159 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity908
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01D - Other beta-lactam antibacterials

    J01DH - Carbapenems

    J01DH06 - Tebipenem pivoxil