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Prestwick3_001120

Prestwick3_001120

Synopsis, Chemistry

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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

Prestwick3_001120

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 Formula	C₁₅H₂₃N₃O₄S
Molecular Weight	341.4 g/mol
XLogP3	1.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	341.14092740 g/mol
Monoisotopic Mass	341.14092740 g/mol
Topological Polar Surface Area	138 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	559
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.