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    Imipenem

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    2D Structure
    Also known as: 64221-86-9, Imipemide, N-formimidoylthienamycin, Imipenem anhydrous, Tienamycin, Imipenemum
    Molecular Formula
    C12H17N3O4S
    Molecular Weight
    299.35  g/mol
    InChI Key
    ZSKVGTPCRGIANV-ZXFLCMHBSA-N
    FDA UNII
    Q20IM7HE75
    Semisynthetic thienamycin that has a wide spectrum of antibacterial activity against gram-negative and gram-positive aerobic and anaerobic bacteria, including many multiresistant strains. It is stable to beta-lactamases. Clinical studies have demonstrated high efficacy in the treatment of infections of various body systems. Its effectiveness is enhanced when it is administered in combination with CILASTATIN, a renal dipeptidase inhibitor.
    Imipenem anhydrous is a Penem Antibacterial.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (5R,6S)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C12H17N3O4S/c1-6(16)9-7-4-8(20-3-2-14-5-13)10(12(18)19)15(7)11(9)17/h5-7,9,16H,2-4H2,1H3,(H2,13,14)(H,18,19)/t6-,7-,9-/m1/s1
    2.1.3 InChI Key
    ZSKVGTPCRGIANV-ZXFLCMHBSA-N
    2.1.4 Canonical SMILES
    CC(C1C2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O
    2.1.5 Isomeric SMILES
    C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)SCCN=CN)O
    2.2 Other Identifiers
    2.2.1 UNII
    Q20IM7HE75
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Anhydrous Imipenem

    2. Anhydrous, Imipenem

    3. Imipemide

    4. Imipenem Anhydrous

    5. Imipenem, Anhydrous

    6. Mk 0787

    7. Mk-0787

    8. Mk0787

    9. N Formimidoylthienamycin

    10. N-formimidoylthienamycin

    2.3.2 Depositor-Supplied Synonyms

    1. 64221-86-9

    2. Imipemide

    3. N-formimidoylthienamycin

    4. Imipenem Anhydrous

    5. Tienamycin

    6. Imipenemum

    7. N-formimidoyl Thienamycin

    8. Imipenem Hydrate

    9. Mk 0787

    10. Chebi:471744

    11. 74431-23-5

    12. Imipenem, N-formimidoyl Thienamycin

    13. (5r,6s)-3-[2-(aminomethylideneamino)ethylsulfanyl]-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

    14. Imipenem (inn)

    15. Imipenem [inn]

    16. (5r,6s)-6-((r)-1-hydroxyethyl)-3-(2-(iminomethylamino)ethylthio)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carbonsaeure

    17. (5r,6s)-3-((2-(formimidoylamino)ethyl)thio)-6-((r)-1-hydroxyethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid

    18. Mk-0787

    19. Chembl148

    20. Q20im7he75

    21. (5r,6s)-3-(2-formimidoylamino-ethylsulfanyl)-6-((r)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

    22. Imipenen

    23. Dsstox_cid_3143

    24. Dsstox_rid_76888

    25. Dsstox_gsid_23143

    26. Anhydrous Imipenem

    27. Imipenem, Anhydrous

    28. Imipenemum [latin]

    29. Cas-64221-86-9

    30. Sr-05000000294

    31. Imipen

    32. Unii-q20im7he75

    33. Ncgc00016928-01

    34. (5r,6s)-6-[(1r)-1-hydroxyethyl]-3-(2-methanimidamidoethylsulfanyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

    35. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-((1r)-1-hydroxyethyl)-3-((2-((iminomethyl)amino)ethyl)thio)-7-oxo-, (5r,6s)-

    36. 1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid, 6-[(1r)-1-hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-, (5r,6s)-

    37. Prestwick_844

    38. Einecs 264-734-5

    39. Mk-787

    40. Mk0787

    41. Imipenem [mi]

    42. Imipenem Anhydrate

    43. Prestwick0_000519

    44. Prestwick1_000519

    45. Prestwick2_000519

    46. Prestwick3_000519

    47. Epitope Id:120384

    48. Imipenem [who-dd]

    49. Bspbio_000477

    50. Bidd:gt0686

    51. Spbio_002398

    52. Bpbio1_000525

    53. Schembl1649260

    54. Schembl8781920

    55. Dtxsid2023143

    56. Gtpl10821

    57. Hy-b1369a

    58. Primaxin (imipenem + Cilastatin)

    59. Hms1569h19

    60. Hms2090a15

    61. Hms2096h19

    62. Hms3260h20

    63. Hms3713h19

    64. Pharmakon1600-01506001

    65. Bcp13012

    66. Zinc4097225

    67. Tox21_110689

    68. Tox21_500279

    69. Bdbm50049708

    70. Bdbm50213266

    71. Nsc717864

    72. Nsc759901

    73. Akos016010844

    74. Tox21_110689_1

    75. Ccg-220519

    76. Ccg-221583

    77. Db01598

    78. Lp00279

    79. Nsc-717864

    80. Sdccgsbi-0633697.p001

    81. Ncgc00167958-01

    82. Ncgc00167958-02

    83. Ncgc00167958-03

    84. Ncgc00167958-05

    85. Ncgc00167958-09

    86. Ncgc00260964-01

    87. (5r,6s)-6-[(1r)-1-hydroxyethyl]-3-({2-[(iminomethyl)amino]ethyl}thio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

    88. 1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid,6-[(1r)-1-hydroxyethyl]-3-[[2-[(iminomethyl)amino]ethyl]thio]-7-oxo-,(5r,6s)-

    89. As-75130

    90. Cs-0077844

    91. C06665

    92. D04515

    93. D96091

    94. Ab01563339_01

    95. Recarbrio (imipenem + Cilastatin + Relebactam).

    96. 847i667

    97. Q425152

    98. Sr-05000000294-2

    99. Sr-05000000294-5

    100. Thienamycin P-nitrobenzylester Hydrochloride(n-methylpyrrolidinonesolvate)

    101. (5r,6s)-3-((2-formimidamidoethyl)thio)-6-((r)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

    102. (5r,6s)-3-({2-[(e)-(aminomethylidene)amino]ethyl}sulfanyl)-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

    103. (5r,6s)-3-(2-formimidamidoethylthio)-6-((r)-1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

    104. (5r,6s)-6-[(1r)-1-hydroxyethyl]-3-[(2-methanimidamidoethyl)sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid

    105. [5r-[5.alpha.,6.alpha.(r*)]]-6-(1-hydroxyethyl)-3-[[2- [(iminomethyl)amino]ethyl]thio]-7-oxo-1-azabicyclo[3.2.0]hept-2- Ene-2-carboxylic Acid Monohydrate

    106. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-(1-hydroxyethyl)-3-((2-((iminomethyl)amino)ethyl)thio)-7-oxo-, (5r-(5-alpha,6-alpha(r*)))-

    107. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-(1-hydroxyethyl)-3-((2-((iminomethyl)amino)ethyl)thio)-7-oxo-, (5r-(5.alpha.,6.alpha.(r*)))-

    108. 103730-39-8

    109. 3-[(2-aminoethyl)thio]-6-[(1r)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid (4-nitrophenyl)methylester Monohydrochloride Compd. With 1-methyl-2-pyrrolidinone (1:1)

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 299.35 g/mol
    Molecular Formula C12H17N3O4S
    XLogP3-0.7
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count6
    Exact Mass299.09397721 g/mol
    Monoisotopic Mass299.09397721 g/mol
    Topological Polar Surface Area142 Ų
    Heavy Atom Count20
    Formal Charge0
    Complexity491
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NamePrimaxin
    PubMed HealthImipenem/Cilastatin (Injection)
    Drug ClassesAntibiotic
    Active Ingredientimipenem; Cilastatin sodium
    Dosage FormInjectable
    RouteInjection
    Strength500mg/vial; 250mg/vial; eq 500mg base/vial; eq 250mg base/vial
    Market StatusPrescription
    CompanyMerck

    2 of 2  
    Drug NamePrimaxin
    PubMed HealthImipenem/Cilastatin (Injection)
    Drug ClassesAntibiotic
    Active Ingredientimipenem; Cilastatin sodium
    Dosage FormInjectable
    RouteInjection
    Strength500mg/vial; 250mg/vial; eq 500mg base/vial; eq 250mg base/vial
    Market StatusPrescription
    CompanyMerck

    4.2 Drug Indication

    Imipenem is indicated, in combination with [cilastatin] with or without [relebactam], for the treatment of bacterial infections including respiratory, skin, bone, gynecologic, urinary tract, and intra-abdominal as well as septicemia and endocarditis.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Imipenem is a beta-lactam antibiotic belongings to the subgroup of carbapenems. Imipenem is active against aerobic and anaerobic Gram positive as well as Gram negative bacteria including Pseudomonas aeruginosa and the Enterococcus. It exerts a bactericidal effects by disrupting cell wall synthesis.

    5.2 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    IMIPENEM ANHYDROUS
    5.3.2 FDA UNII
    Q20IM7HE75
    5.3.3 Pharmacological Classes
    Established Pharmacologic Class [EPC] - Penem Antibacterial
    5.4 ATC Code

    J01DH51

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    5.5 Absorption, Distribution and Excretion

    Absorption

    Imipenem is not effectively absorbed from the gastrointestinal tract and therefore must be administered parenterally. The bioavailability of the IM injection is 89%.

    Route of Elimination

    Approximately 70% of imipenem is excreted in the urine as the parent drug.

    Volume of Distribution

    The reported volume of distribution for imipenem ranges from 0.23-0.31 L/kg.

    Clearance

    The total clearance of imipenem is 0.2 L/h/kg. When used alone, the renal clearance is 0.05 L/h/kg. In combination with cilastatin the renal clearance of imipenem is 0.15 L/h/kg, likely due to the increased concentration of the parent drug.

    5.6 Metabolism/Metabolites

    Imipenem is metabolized by renal dehydropeptidase.

    5.7 Biological Half-Life

    When given via IV injection imipenem has a half-life of 1 h. The apparent half-life of the IM injection ranges from 1.3-5.1 h, likely due to slower absorption form the injection site.

    5.8 Mechanism of Action

    Imipenem acts as an antimicrobial through the inhibition of cell wall synthesis of various gram-positive and gram-negative bacteria. This inhibition of cell wall synthesis in gram-negative bateria is attained by binding to penicillin-binding proteins (PBPs). In E. coli and selected strains of P. aeruginosa, imipenem has shown to have the highest affinity to PBP-2, PBP-1a, and PBP-1b. This inhibition of PBPs prevents the bacterial cell from adding to the peptidoglycan polymer which forms the bacterial cell wall eventually leading to cell death.