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    Cyclacillin

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    PharmaCompass
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    2D Structure
    Also known as: Ciclacillin, Vastcillin, Ciclacillum, Bastcillin, 3485-14-1, Cyclapen
    Molecular Formula
    C15H23N3O4S
    Molecular Weight
    341.4  g/mol
    InChI Key
    HGBLNBBNRORJKI-WCABBAIRSA-N
    FDA UNII
    72ZJ154X86
    A cyclohexylamido analog of PENICILLANIC ACID.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C15H23N3O4S/c1-14(2)9(12(20)21)18-10(19)8(11(18)23-14)17-13(22)15(16)6-4-3-5-7-15/h8-9,11H,3-7,16H2,1-2H3,(H,17,22)(H,20,21)/t8-,9+,11-/m1/s1
    2.1.3 InChI Key
    HGBLNBBNRORJKI-WCABBAIRSA-N
    2.1.4 Canonical SMILES
    CC1(C(N2C(S1)C(C2=O)NC(=O)C3(CCCCC3)N)C(=O)O)C
    2.1.5 Isomeric SMILES
    CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C3(CCCCC3)N)C(=O)O)C
    2.2 Other Identifiers
    2.2.1 UNII
    72ZJ154X86
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Aminocyclohexylpenicillin

    2. Ciclacillin

    3. Wy 4508

    4. Wy-4508

    5. Wy4508

    2.3.2 Depositor-Supplied Synonyms

    1. Ciclacillin

    2. Vastcillin

    3. Ciclacillum

    4. Bastcillin

    5. 3485-14-1

    6. Cyclapen

    7. Aminocyclohexylpenicillin

    8. Citosarin

    9. Syngacillin

    10. Ultracillin

    11. Calthor

    12. Vipicil

    13. Wyvital

    14. Cyclapen-w

    15. Orfilina

    16. Ciclacilline

    17. Ciclacillinum

    18. (1-aminocyclohexyl)penicillin

    19. Ciclacilina

    20. Ciclacilina [inn-spanish]

    21. Ciclacilline [inn-french]

    22. Ciclacillinum [inn-latin]

    23. 6-(1-aminocyclohexanecarboxamido)penicillanic Acid

    24. Aminocyclohexyl Penicillin

    25. Wy-4508

    26. Cyclacillin [usan]

    27. 6-(1-aminocyclohexylcarboxamido)penicillanic Acid

    28. Wy 4508

    29. Ac 98

    30. Penicillin, (aminocyclohexyl)-

    31. Ciclacillin [inn]

    32. Cyclacillin (usan)

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

    34. Nsc88789

    35. Nsc-88789

    36. (2s,5r,6r)-6-{[(1-aminocyclohexyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    37. Noblicil

    38. Peamezin

    39. Chebi:31444

    40. 72zj154x86

    41. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((1-aminocyclohexyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2s-(2alpha,5alpha,6beta))-

    42. 6-(1-aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid

    43. Ncgc00016629-01

    44. Cas-3485-14-1

    45. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(1-aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, (2s,5r,6r)-

    46. Ac-pc

    47. Vastcillin (tn)

    48. 6-(1-aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    49. Cyclapen-w (tn)

    50. Mls002694856

    51. Einecs 222-470-8

    52. Nsc 88789

    53. Wy4508

    54. Cyclacillin [usan:usp]

    55. Brn 0938663

    56. Unii-72zj154x86

    57. Cyclacillin [mi]

    58. Prestwick0_001120

    59. Prestwick1_001120

    60. Prestwick2_001120

    61. Prestwick3_001120

    62. Ciclacillin [jan]

    63. Dsstox_cid_2861

    64. Ciclacillin (jp17/inn)

    65. Cyclacillin [vandf]

    66. Ciclacillin [mart.]

    67. Dsstox_rid_76762

    68. C-12104

    69. Dsstox_gsid_22861

    70. Schembl33900

    71. Bspbio_001260

    72. Ciclacillin [who-dd]

    73. Spbio_003120

    74. Bpbio1_001385

    75. Gtpl4817

    76. Chembl1200356

    77. Dtxsid9022861

    78. Cyclacillin [orange Book]

    79. Hms1571o22

    80. Zinc3830609

    81. Tox21_110534

    82. Bdbm50350474

    83. 6beta-(1-aminocyclohexanecarboxamido)-2,2-dimethylpenam-3alpha-carboxylic Acid

    84. Db01000

    85. Ncgc00179238-01

    86. (2s,5r,6r)-6-(1-aminocyclohexaneamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    87. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(1-aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo-

    88. Hy-16158

    89. Nci60_041965

    90. Ab00514059

    91. Cs-0006169

    92. D01334

    93. Q5119441

    94. Brd-k89046952-001-03-4

    95. Wln: T45 Anv Estj F1 F1 Gvq Cmv- Al6tj Az

    96. (2s,5r,6r)-6-[(1-aminocyclohexane)amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 341.4 g/mol
    Molecular Formula C15H23N3O4S
    XLogP31.3
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count3
    Exact Mass341.14092740 g/mol
    Monoisotopic Mass341.14092740 g/mol
    Topological Polar Surface Area138 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity559
    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 Indication

    For the treatment of bacterial infections caused by susceptible organisms.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Cyclacillin, a penicillin, is a cyclohexylamido analog of penicillanic acid. Cyclacillin is more resistant to beta-lactamase hydrolysis than ampicillin, is much better absorbed when given by mouth and, as a result, the levels reached in the blood and in the urine are considerably higher than those obtained with the same dose of ampicillin. Cyclacillin has been replaced by newer penicillin treatments.

    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 Absorption, Distribution and Excretion

    Absorption

    Moderately absorbed.

    5.4 Mechanism of Action

    The bactericidal activity of cyclacillin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cyclacillin is stable in the presence of a variety of b-lactamases, including penicillinases and some cephalosporinases.