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    Azlocillin

    PharmaCompass
    Xls

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    2D Structure
    Also known as: 37091-66-0, Azlocilina, Azlocilline, Azlocillinum, Azlocilina [inn-spanish], Azlocilline [inn-french]
    Molecular Formula
    C20H23N5O6S
    Molecular Weight
    461.5  g/mol
    InChI Key
    JTWOMNBEOCYFNV-NFFDBFGFSA-N
    FDA UNII
    HUM6H389W0
    A semisynthetic ampicillin-derived acylureido penicillin.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11-,12-,13+,16-/m1/s1
    2.1.3 InChI Key
    JTWOMNBEOCYFNV-NFFDBFGFSA-N
    2.1.4 Canonical SMILES
    CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)NC(=O)N4CCNC4=O)C(=O)O)C
    2.1.5 Isomeric SMILES
    CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)NC(=O)N4CCNC4=O)C(=O)O)C
    2.2 Other Identifiers
    2.2.1 UNII
    HUM6H389W0
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Azlin

    2. Azlocillin Sodium

    3. Azlocillin, Sodium

    4. Bay E 6905

    5. Bay-e 6905

    6. Baye 6905

    7. Securopen

    8. Sodium Azlocillin

    9. Sodium, Azlocillin

    2.3.2 Depositor-Supplied Synonyms

    1. 37091-66-0

    2. Azlocilina

    3. Azlocilline

    4. Azlocillinum

    5. Azlocilina [inn-spanish]

    6. Azlocilline [inn-french]

    7. Azlocillinum [inn-latin]

    8. Chebi:2956

    9. Azlocillin Sodium Salt

    10. Hum6h389w0

    11. J01ca09

    12. Nsc-758227

    13. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-((r)-2-(2-oxo-1-imidazolidinecarboxamido)-2-phenylacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid

    14. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-{[(2r)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    15. 37091-65-9

    16. Azlocillin (usan/inn)

    17. Unii-hum6h389w0

    18. Azlocillin [usan:inn:ban]

    19. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-(((2r)-2-(((2-oxoimidazolidin-1-yl)carbonyl)amino)-2-phenylacetyl)amino)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid

    20. Einecs 253-348-2

    21. Azlocillin [mi]

    22. Azlocillin [inn]

    23. Prestwick3_000821

    24. Azlocillin [usan]

    25. Azlocillin [vandf]

    26. Epitope Id:141185

    27. 6-((r)-2-(2-oxoimidazolidin-1-carboxamido)-2-phenylacetamido)penicillansaeure

    28. Azlocillin [mart.]

    29. Azlocillin [who-dd]

    30. Chembl1537

    31. Schembl34150

    32. Bspbio_000741

    33. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[[(2r)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    34. Bpbio1_000817

    35. Dtxsid1022639

    36. Zinc3830261

    37. Akos025402328

    38. Ac-8140

    39. Db01061

    40. Ds-3291

    41. Nsc 758227

    42. 2,2-dimethyl-6beta-[(2r)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetamido]penam-3alpha-carboxylic Acid

    43. 91a659

    44. C06839

    45. D02339

    46. D81792

    47. A823527

    48. Q510154

    49. Brd-k60663764-236-02-1

    50. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-((r)-2-(2-oxoimidazolidine-1-carboxamido)-2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    51. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[(2r)-2-{[(2-oxoimidazolidin-1-yl)carbonyl]amino}-2-phenylacetamido]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    52. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[[(2r)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenyl-acetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    53. (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[[(2s)-2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenyl-acetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid;azlocillin

    54. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-(((((2-oxo-1-imidazolidinyl)carbonyl)amino)phenylacetyl)amino)-, (2s-(2.alpha.,5.alpha.,6.beta.(s*)))-

    55. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-(((((2-oxo-1-imidazolidinyl)carbonyl)amino)phenylacetyl)amino)-, (2s-(2alpha,5alpha,6beta(s*)))-

    56. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-[[[[((r)-2-oxo-1-imidazolidinyl)carbonyl]amino]phenylacetyl]amino]-, (2s,5r,6r)-

    57. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid,3,3-dimethyl-7-oxo-6-[[[[(2-oxo-1-imidazolidinyl)carbonyl]amino]phenylacetyl]amino]-, [2s-[2a,5a,6b(s*)]]-

    2.4 Create Date
    2006-04-29
    3 Chemical and Physical Properties
    Molecular Weight 461.5 g/mol
    Molecular Formula C20H23N5O6S
    XLogP30.1
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count5
    Exact Mass461.13690464 g/mol
    Monoisotopic Mass461.13690464 g/mol
    Topological Polar Surface Area173 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity844
    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

    For the treatment of infections caused by Pseudomonas aeruginosa, Escherichia coli, and Haemophilus influenzae.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Similar to [mezlocillin] and [piperacillin], azlocillin is an acylampicillin that exhibits an extended-spectrum of activity and _in vitro_ potency that is greater than that of the carboxy penicillins. Azlocillin is shown to be effective against a broad spectrum of bacteria, including Pseudomonas aeruginosa and enterococci.

    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 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01C - Beta-lactam antibacterials, penicillins

    J01CA - Penicillins with extended spectrum

    J01CA09 - Azlocillin

    5.4 Absorption, Distribution and Excretion

    Absorption

    Not significantly absorbed from the gastrointestinal tract.

    5.5 Metabolism/Metabolites

    Eliminated predominantly by renal mechanisms, but also undergoes biotransformation within body tissues and intraintestinal degradation by bowel bacteria, with high concentrations found in bile.

    5.6 Biological Half-Life

    Mean elimination half-life is 1.3 to 1.5 hours. Longer in neonates, and 2 to 6 hours in patients with renal impairment.

    5.7 Mechanism of Action

    By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, azlocillin 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; it is possible that azlocillin interferes with an autolysin inhibitor.