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    Hetacillin

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    PharmaCompass
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    2D Structure
    Also known as: 3511-16-8, Hetacillinum, Phenazacillin, Hetacilina, Hetacilline, Versapen
    Molecular Formula
    C19H23N3O4S
    Molecular Weight
    389.5  g/mol
    InChI Key
    DXVUYOAEDJXBPY-NFFDBFGFSA-N
    FDA UNII
    TN4JSC48CV
    Hetacillin is a semi-synthetic penicillin compound with bactericidal properties. Hetacillin is a prodrug that is converted to ampicillin via esterases. Ampicillin binds to inactivated penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs, including transpeptidases, carboxypeptidases, and endopeptidases, participate in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. This results in the weakening of the bacterial cell wall and eventually causes cell lysis. (NCI05)
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (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-carboxylic acid
    2.1.2 InChI
    InChI=1S/C19H23N3O4S/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)/t11-,12-,13+,16-/m1/s1
    2.1.3 InChI Key
    DXVUYOAEDJXBPY-NFFDBFGFSA-N
    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
    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
    2.2 Other Identifiers
    2.2.1 UNII
    TN4JSC48CV
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Hetacillin, (2s-(2alpha,5alpha,6alpha))-isomer

    2. Hetacillin, Aluminum Salt (3:1), (2s-(2alpha,5alpha,6beta(s*)))-isomer

    3. Hetacillin, Monopotassium Salt, (2s-(2alpha,5alpha,6beta(s*)))-isomer

    4. Hetacillin, Monosodium Salt, (2s-(2alpha,5alpha,6beta(s*)))-isomer

    5. Hetacillin, Monosodium Salt, (2s-(2alpha,5alpha,6beta))-isomer

    6. Phenazacillin

    2.3.2 Depositor-Supplied Synonyms

    1. 3511-16-8

    2. Hetacillinum

    3. Phenazacillin

    4. Hetacilina

    5. Hetacilline

    6. Versapen

    7. Bl-p 804

    8. Hetacillin Acid

    9. Brl-804

    10. Tn4jsc48cv

    11. Chebi:5683

    12. (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-carboxylic Acid

    13. Blp-804

    14. Bl-p-804

    15. 6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid

    16. 7-(2,2-dimethyl-5-oxo-4-phenyl-imidazolidin-1-yl)-3,3-dimethyl-6-oxo-2-thia-5-azabicyclo[3.2.0]heptane-4-carboxylic Acid

    17. Etacillina

    18. 6beta-[(4r)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanic Acid

    19. Etacillina [dcit]

    20. Brl 804

    21. Unii-tn4jsc48cv

    22. Hetacilina [inn-spanish]

    23. Hetacilline [inn-french]

    24. Hetacillinum [inn-latin]

    25. Hetacillin [usan:usp:inn:ban]

    26. Versapen (tn)

    27. Einecs 222-512-5

    28. Hetacillin [mi]

    29. Hetacillin [inn]

    30. Hetacillin (usan/inn)

    31. Hetacillin [usan]

    32. N,n'-isopropylidene-a-amino-benzyl Penicillin

    33. Hetacillin [mart.]

    34. Hetacillin [who-dd]

    35. Schembl34131

    36. Chembl1201116

    37. Dtxsid4023121

    38. Hetacillin [orange Book]

    39. Zinc4102186

    40. 6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)penicillansaeure

    41. Hy-16251a

    42. Cs-4870

    43. Db00739

    44. (2s,%r,6r)-6-(2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure

    45. D01074

    46. Q5746710

    47. (2s,5r,6r)-6-((r)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    48. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((4r)-2,2-dimethyl-5-oxo-4-phenyl-1-imidazolidinyl)-3,3-dimethyl-7-oxo-, (2s,5r,6r)-

    49. 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-, (2s-(2.alpha.,5.alpha.,6.beta.(s*)))-

    50. 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-, (2s-(2alpha,5alpha,6beta(s*)))-

    51. 6beta-[(4r)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-2,2-dimethylpenam-3alpha-carboxylic Acid

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 389.5 g/mol
    Molecular Formula C19H23N3O4S
    XLogP3-0.6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count3
    Exact Mass389.14092740 g/mol
    Monoisotopic Mass389.14092740 g/mol
    Topological Polar Surface Area115 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity688
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Hetacillin is a beta-lactam antibiotic prodrug used to treat bacterial infections. In the body it gets converted to ampicillin.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Hetacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Hetacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Hetacillin results from the inhibition of cell wall synthesis and is mediated through Hetacillin binding to penicillin binding proteins (PBPs).

    5.2 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01C - Beta-lactam antibacterials, penicillins

    J01CA - Penicillins with extended spectrum

    J01CA18 - Hetacillin

    5.3 Metabolism/Metabolites

    Hydrolyzed to active ampicillin via esterases

    5.4 Mechanism of Action

    Hetacillin is a semisynthetic penicillin prodrug which itself has no antibacterial activity, but is converted in the body to ampicillin and has actions and uses similar to those of ampicillin. Hetacillin is prepared by reacting ampicillin with acetone. Ampicillin rapidly decomposes because of the intramolecular attack of the side chain amino group on the lactam ring. _In vitro_ studies have shown that hetacillin is resistant to beta lactamase activity. However, this effect is transient, as the hydrolysis product, ampicillin, is readily inactivated by beta lactamase. Hetacillin locks up the offending amino group and prevents the decomposition of Hetacillin. Once hydrolyzed to ampicillin (and acetone), ampicillin binds to the penicillin binding proteins found in susceptible bacteria. This inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins.