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    Ertapenem Sodium

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    2D Structure
    Also known as: Ertapenem sodium, Ertapenem monosodium, Ertapenem sodium [usan], Ertapenem monosodium (90per cent), 153773-82-1, Mk 0826
    Molecular Formula
    C22H24N3NaO7S
    Molecular Weight
    497.5  g/mol
    InChI Key
    ZXNAQFZBWUNWJM-HRXMHBOMSA-M
    A carbapenem derivative antibacterial agent that is more stable to renal dehydropeptidase I than IMIPENEM, but does not need to be given with an enzyme inhibitor such as CILASTATIN. It is used in the treatment of Gram-positive and Gram-negative bacterial infections including intra-abdominal infections, acute gynecological infections, complicated urinary tract infections, skin infections, and respiratory tract infections. It is also used to prevent infection in colorectal surgery.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    sodium;(4R,5S,6S)-3-[(3S,5S)-5-[(3-carboxylatophenyl)carbamoyl]pyrrolidin-1-ium-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/C22H25N3O7S.Na/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30;/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32);/q;+1/p-1/t9-,10-,13+,14+,15-,16-;/m1./s1
    2.1.3 InChI Key
    ZXNAQFZBWUNWJM-HRXMHBOMSA-M
    2.1.4 Canonical SMILES
    CC1C2C(C(=O)N2C(=C1SC3CC([NH2+]C3)C(=O)NC4=CC=CC(=C4)C(=O)[O-])C(=O)[O-])C(C)O.[Na+]
    2.1.5 Isomeric SMILES
    C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H]([NH2+]C3)C(=O)NC4=CC=CC(=C4)C(=O)[O-])C(=O)[O-])[C@@H](C)O.[Na+]
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Ertapenem

    2. Ertapenem Sodium

    3. Invanoz

    2.2.2 Depositor-Supplied Synonyms

    1. Ertapenem Sodium

    2. Ertapenem Monosodium

    3. Ertapenem Sodium [usan]

    4. Ertapenem Monosodium (90per Cent)

    5. 153773-82-1

    6. Mk 0826

    7. Sodium;(4r,5s,6s)-3-[(3s,5s)-5-[(3-carboxylatophenyl)carbamoyl]pyrrolidin-1-ium-3-yl]sulfanyl-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    8. 2t90ke67l0

    9. Mk 826

    10. Unii-2t90ke67l0

    11. L 749345

    12. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 3-(((3s,5s)-5-(((3-carboxyphenyl)amino)carbonyl)-3-pyrrolidinyl)thio)-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-, Monosodium Salt, (4r,5s,6s)-

    13. 1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 3-((5-(((3-carboxyphenyl)amino)carbonyl)-3-pyrrolidinyl)thio)-6-((1r)-1-hydroxyethyl)-4-methyl-7-oxo-, Monosodium Salt, (4r-(3(3s*,5s*),4alpha,5beta,6beta(r*)))-

    14. Sodium (4r,5s,6s)-3-({(3s,5s)-5-[(3-carboxylatophenyl)carbamoyl]pyrrolidinium-3-yl}sulfanyl)-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    15. Sodium (4r,5s,6s)-3-({(3s,5s)-5-[(m-carboxylatophenyl)carbamoyl]pyrrolidinium-3-yl}sulfanyl)-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    16. Sodium (4r,5s,6s)-3-({(3s,5s)-5-[(m-carboxyphenyl)carbamoyl]-3-pyrrolidinyl}thio)-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

    2.3 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 497.5 g/mol
    Molecular Formula C22H24N3NaO7S
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count5
    Exact Mass497.12326557 g/mol
    Monoisotopic Mass497.12326557 g/mol
    Topological Polar Surface Area192 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity882
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Indication

    * Treatment:

    Treatment of the following infections when caused by bacteria known or very likely to be susceptible to ertapenem and when parenteral therapy is required:

    - intra-abdominal infections;

    - community-acquired pneumonia;

    - acute gynaecological infections;

    - diabetic foot infections of the skin and soft tissue.

    * Prevention:

    Invanz is indicated in adults for the prophylaxis of surgical site infection following elective colorectal surgery.

    Consideration should be given to official guidance on the appropriate use of antibacterial agents.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Anti-Bacterial Agents

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

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Penem Antibacterial [EPC]; Carbapenems [CS]
    5.3 ATC Code

    J01DH03