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Synopsis

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Chemistry

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Also known as: 4800-94-6, Carbenicillin disodium salt, Carbenicillin sodium, Carbecin, Geopen, Microcillin

Molecular Formula

C₁₇H₁₆N₂Na₂O₆S

Molecular Weight

422.4 g/mol

InChI Key

RTYJTGSCYUUYAL-YCAHSCEMSA-L

FDA UNII

9TS4B3H261

Broad-spectrum semisynthetic penicillin derivative used parenterally. It is susceptible to gastric juice and penicillinase and may damage platelet function.

1 2D Structure

Carbenicillin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

disodium;(2S,5R,6R)-6-[(2-carboxylato-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

2.1.2 InChI

InChI=1S/C17H18N2O6S.2Na/c1-17(2)11(16(24)25)19-13(21)10(14(19)26-17)18-12(20)9(15(22)23)8-6-4-3-5-7-8;;/h3-7,9-11,14H,1-2H3,(H,18,20)(H,22,23)(H,24,25);;/q;2*+1/p-2/t9?,10-,11+,14-;;/m1../s1

2.1.3 InChI Key

RTYJTGSCYUUYAL-YCAHSCEMSA-L

2.1.4 Canonical SMILES

CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)C(=O)[O-])C(=O)[O-])C.[Na+].[Na+]

2.1.5 Isomeric SMILES

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C(C3=CC=CC=C3)C(=O)[O-])C(=O)[O-])C.[Na+].[Na+]

2.2 Other Identifiers

2.2.1 UNII

9TS4B3H261

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Anabactyl

2. Carbapen

3. Carbecin

4. Carbenicillin

5. Carboxybenzyl Penicillin

6. Disodium, Carbenicillin

7. Geopen

8. Microcillin

9. Penicillin, Carboxybenzyl

10. Pyopen

2.3.2 Depositor-Supplied Synonyms

1. 4800-94-6

2. Carbenicillin Disodium Salt

3. Carbenicillin Sodium

4. Carbecin

5. Geopen

6. Microcillin

7. Pyopen

8. Pyocianil

9. Hyoper

10. Disodium Carbenicillin

11. Alpha-carboxybenzylpenicillin Disodium Salt

12. Brl-2064

13. Cp-15-639-2

14. Sodium Carbenicillin

15. Nsc-111071

16. Alpha-carboxybenzylpenicillin Sodium Salt

17. Disodium Alpha-carboxybenzylpenicillin

18. Anabactyl

19. Fugacillin

20. Gripenin

21. Piopen

22. Carbenicilline Disodium

23. N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)-hept-6-yl)-2-phenylmalonamic Acid Disodium Salt

24. Chebi:34609

25. 9ts4b3h261

26. Cp 15639-2

27. Gs 3159 Disodium Salt

28. Pyoclox

29. Carbenicillin Sodium (jan)

30. Dsstox_cid_25820

31. Dsstox_rid_81153

32. Dsstox_gsid_45820

33. Carbenicillin (disodium)

34. Carboxybenzylpenicillin Sodium

35. Brl 2064

36. Carbenicillin Sodium [jan]

37. Carbenicillin, Disodium Salt

38. Sodium (2s,5r,6r)-6-(2-carboxylato-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

39. Cas-4800-94-6

40. Carbenicillin Disodium [usan]

41. Einecs 225-360-8

42. Nsc 111071

43. Unii-9ts4b3h261

44. Prestwick_29

45. Carbencillin Sodium

46. Ncgc00094607-01

47. Carbenicillin Disodium [usan:usp]

48. Geopen (tn)

49. Mfcd00077683

50. Schembl54797

51. Carbenicillin Disodium (usp)

52. Spectrum1500160

53. Chembl606260

54. Dtxsid6045820

55. Hms502e17

56. Hms1920i19

57. Hms2091o21

58. Tox21_111304

59. Carbenicillin Sodium [mart.]

60. Ccg-38928

61. S3179

62. Carbenicillin Disodium [vandf]

63. Akos016001461

64. Tox21_111304_1

65. Carbenicillin Disodium [who-dd]

66. Carbenicillin Disodium Salt [mi]

67. Ncgc00022579-05

68. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((carboxyphenylacetyl)amino)-3,3-dimethyl-7-oxo, Disodium Salt, (2s-(2alpha,5alpha,6beta))-

69. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((carboxyphenylacetyl)amino)-3,3-dimethyl-7-oxo, Disodium Salt, (6s-(2alpha,5alpha,6beta))-

70. As-11636

71. Disodium (2s-(2alpha,5alpha,6beta))-6-(carboxylatophenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

72. Malonamic Acid, N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)hept-6-yl)-2-phenyl-, Disodium Salt

73. Carbenicillin Disodium [orange Book]

74. Carbenicillin Disodium [usp Impurity]

75. Sw220220-1

76. D02190

77. F14953

78. Q27116177

79. Carbenicillin Disodium, Meets Usp Testing Specifications

80. Carbenicillin Disodium Salt, 89.0-100.5% Anhydrous Basis

81. Carbenicillin Disodium Salt, Bioreagent, Plant Cell Culture Tested

82. Carbenicillin Sodium, European Pharmacopoeia (ep) Reference Standard

83. Disodium 6beta-(2-carboxylato-2-phenylacetamido)-2,2-dimethylpenam-3alpha-carboxylate

84. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((carboxyphenylacetyl)amino)-3,3-dimethyl-7-oxo, Disodium Salt, (2s-(2.alpha.,5.alpha.,6.beta.))

85. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid, 6-[(2-carboxy-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-, Sodium Salt, (2s,5r,6r)- (1:2)

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

87. Disodium (2s,5r,6r)-6-{[carboxylato(phenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

88. Disodium;(2s,5r,6r)-6-[(2-carboxylato-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

89. Sodium(2s,5r,6r)-6-(2-carboxylato-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₆N₂Na₂O₆S
Molecular Weight	422.4 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	3
Exact Mass	422.05244597 g/mol
Monoisotopic Mass	422.05244597 g/mol
Topological Polar Surface Area	155 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	634
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

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