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    Biapenem

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    2D Structure
    Also known as: 120410-24-4, Omegacin, Biapenern, L-627, Ljc-10627, Lj c10,627
    Molecular Formula
    C15H18N4O4S
    Molecular Weight
    350.4  g/mol
    InChI Key
    MRMBZHPJVKCOMA-YJFSRANCSA-N
    FDA UNII
    YR5U3L9ZH1
    Biapenem is a 1-beta-methylcarbapenem antibiotic with a wide range of antibacterial activity. Biapenem has similar antibacterial activity to that of imipenem, but is more stable against human renal dehydropeptidase-I and with less neurotoxicity.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (4R,5S,6S)-3-(6,7-dihydro-5H-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylsulfanyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
    2.1.2 InChI
    InChI=1S/C15H18N4O4S/c1-7-11-10(8(2)20)14(21)19(11)12(15(22)23)13(7)24-9-3-17-5-16-6-18(17)4-9/h5-11,20H,3-4H2,1-2H3/t7-,8-,10-,11-/m1/s1
    2.1.3 InChI Key
    MRMBZHPJVKCOMA-YJFSRANCSA-N
    2.1.4 Canonical SMILES
    CC1C2C(C(=O)N2C(=C1SC3CN4C=NC=[N+]4C3)C(=O)[O-])C(C)O
    2.1.5 Isomeric SMILES
    C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1SC3CN4C=NC=[N+]4C3)C(=O)[O-])[C@@H](C)O
    2.2 Other Identifiers
    2.2.1 UNII
    YR5U3L9ZH1
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3-((6,7-dihydro-5h-pyrazolo(1,2-a)(1,2,4)triazol-4-ium-6-yl)thio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3,2,0)hept-2-ene-2-carboxylate

    2. Cli 86,815

    3. Cli 86815

    4. Cli-86815

    5. L 627

    6. L-627

    7. Ljc 10627

    8. Ljc-10627

    9. Ljc10,627

    2.3.2 Depositor-Supplied Synonyms

    1. 120410-24-4

    2. Omegacin

    3. Biapenern

    4. L-627

    5. Ljc-10627

    6. Lj C10,627

    7. Cl 186,815

    8. L 627

    9. Cl-186815

    10. Rpx2003

    11. (4r,5s,6s)-3-(6,7-dihydro-5h-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylsulfanyl)-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    12. Yr5u3l9zh1

    13. Chebi:3089

    14. Lj-c10627

    15. (4r,5s,6s)-3-((6,7-dihydro-5h-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-yl)thio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    16. 6-(((4r,5s,6s)-2-carboxy-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-en-3-yl)thio)-6,7-dihydro-5h-pyrazolo(1,2-a)-s-triazol-4-ium Hydroxide, Inner Salt

    17. Biapenem [usan:inn]

    18. Omegacin (tn)

    19. (4r,5s,6s)-3-(6,7-dihydro-5h-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylthio)-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    20. (6s)-2-(6,7-dihydro-5h-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylsulfanyl)-6-[(1r)-1-hydroxyethyl]-1beta-methyl-2,3-didehydro-1-carbapenam-3-carboxylate

    21. Biapenem;(4r,5s,6s)-3-(6,7-dihydro-5h-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylthio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    22. Ljc 10627

    23. Unii-yr5u3l9zh1

    24. Bipenem

    25. Ncgc00164551-01

    26. Ljc10627

    27. Cli 86815

    28. Ljc10,627

    29. Mfcd00864863

    30. Biapenem [usan]

    31. Biapenem [inn]

    32. Biapenem [jan]

    33. Biapenem [mi]

    34. Biapenem [mart.]

    35. Biapenem [who-dd]

    36. Dsstox_cid_26435

    37. Dsstox_rid_81612

    38. Dsstox_gsid_46435

    39. Schembl49242

    40. Biapenem (jan/usan/inn)

    41. Chembl285347

    42. Biapenem, >=98% (hplc)

    43. Dtxsid5046435

    44. Gtpl12022

    45. Ex-a4945

    46. Tox21_112180

    47. S1370

    48. Akos025149478

    49. Ccg-268031

    50. Cs-2071

    51. Db13028

    52. Ncgc00164551-02

    53. Ncgc00164551-05

    54. As-14655

    55. Hy-13573

    56. L627

    57. Cas-120410-24-4

    58. D01057

    59. A804499

    60. Q-101421

    61. Q4902548

    62. (4r,5s,6s)-3-(6,7-dihydro-5h-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylthio)-6-((r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    63. (4r,5s,6s)-3-(6,7-dihydro-5h-pyrazolo[1,2-a][1,2,4]triazol-4-ium-6-ylthio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    64. 5h-pyrazolo(1,2-a)(1,2,4)triazol-4-ium, 6-((2-carboxy-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-en-3-yl)thio)-6,7-dihydro-, Hydroxide, Inner Salt, (4r-(4.alpha.,5.beta.,6.beta.(r*)))-

    65. 6-(((4r,5s,6s)-2-carboxy-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo(3.2.0)hept-2-en-3-yl)thio)-6,7-dihydro-5h-pyrazolo(1,2-a)(1,2,4)triazol-4-ium Inner Salt

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 350.4 g/mol
    Molecular Formula C15H18N4O4S
    XLogP31.4
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count3
    Exact Mass350.10487624 g/mol
    Monoisotopic Mass350.10487624 g/mol
    Topological Polar Surface Area128 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity609
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Anti-Infective Agents

    Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

    4.2 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01D - Other beta-lactam antibacterials

    J01DH - Carbapenems

    J01DH05 - Biapenem