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    Hetacillin Potassium

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    PharmaCompass
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    2D Structure
    Also known as: Natacillin, 5321-32-4, Potassium hetacillin, Versapen-k, Hetacillin (potassium), Versatrex
    Molecular Formula
    C19H22KN3O4S
    Molecular Weight
    427.6  g/mol
    InChI Key
    QRSPJBLLJXVPDD-XFAPPKAWSA-M
    FDA UNII
    95PFX5932Y
    Hetacillin Potassium is the potassium salt of hetacillin, a semi-synthetic penicillin antibiotic with bactericidal activity. Hetacillin is a prodrug that is converted to ampicillin via esterases. Ampicillin binds to and inactivated penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall, thereby preventing the cross-linkage of peptidoglycans, which are critical components of the bacterial cell wall. This leads to an interruption of the bacterial cell wall and causes bacterial cell lysis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    potassium;(2S,5R,6R)-6-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
    2.1.2 InChI
    InChI=1S/C19H23N3O4S.K/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10;/h5-9,11-13,16,20H,1-4H3,(H,25,26);/q;+1/p-1/t11-,12-,13+,16-;/m1./s1
    2.1.3 InChI Key
    QRSPJBLLJXVPDD-XFAPPKAWSA-M
    2.1.4 Canonical SMILES
    CC1(C(N2C(S1)C(C2=O)N3C(=O)C(NC3(C)C)C4=CC=CC=C4)C(=O)[O-])C.[K+]
    2.1.5 Isomeric SMILES
    CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N3C(=O)[C@H](NC3(C)C)C4=CC=CC=C4)C(=O)[O-])C.[K+]
    2.2 Other Identifiers
    2.2.1 UNII
    95PFX5932Y
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Natacillin

    2. 5321-32-4

    3. Potassium Hetacillin

    4. Versapen-k

    5. Hetacillin (potassium)

    6. Versatrex

    7. Hetacin-k

    8. Chebi:34789

    9. 95pfx5932y

    10. Nsc-757046

    11. Potassium 6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

    12. Potassium;(2s,5r,6r)-6-[(4r)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

    13. Hetacin-k (veterinary)

    14. H-k Mastitis (veterinary)

    15. Unii-95pfx5932y

    16. Einecs 226-182-3

    17. Hetacin-k (tn)

    18. Hetacillin Potassium [usan:usp:jan]

    19. Hetacillin Potassium Salt

    20. Schembl192601

    21. Chembl1201121

    22. Hetacillin Potassium (jan/usan)

    23. Hetacillin Potassium [jan]

    24. Hetacillin Potassium [usan]

    25. Hetacillin Potassium [mart.]

    26. Hetacillin Potassium [who-dd]

    27. Hetacillin Potassium Salt [mi]

    28. Cs-4871

    29. Nsc 757046

    30. Hetacillin Potassium [green Book]

    31. Hetacillin Potassium [orange Book]

    32. Hy-16251

    33. D02203

    34. Q27116274

    35. Potassium 6beta-[(4r)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanate

    36. 26939-80-0

    37. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-, Monopotassium Salt, (2s-(2.alpha.,5.alpha.,6.beta.(s*)))-

    38. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-, Monopotassium Salt, (2s-(2alpha,5alpha,6beta(s*)))-

    39. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(2,2-dimethyl-5-oxo-4-phenyl-imidazolinyl)-3,3-dimethyl-7-oxo-, Monopotassium Salt

    40. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid,6-[(4r)-2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl]-3,3-dimethyl-7-oxo-,potassium Salt(1:1),(2s,5r,6r)-

    41. Potassium (2s,5r,6r)-6-[(4r)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

    42. Potassium (2s-(2alpha,5alpha,6beta(s*)))-6-(2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

    43. Potassium 6beta-[(4r)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-2,2-dimethylpenam-3alpha-carboxylate

    2.4 Create Date
    2008-02-05
    3 Chemical and Physical Properties
    Molecular Weight 427.6 g/mol
    Molecular Formula C19H22KN3O4S
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count3
    Exact Mass427.09680885 g/mol
    Monoisotopic Mass427.09680885 g/mol
    Topological Polar Surface Area118 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity695
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2