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DSSTox_CID_3605

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Also known as: 68373-14-8, Sulbactam acid, Betamaze, Penicillanic acid sulfone, (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide, Sulbactamum

Molecular Formula

C₈H₁₁NO₅S

Molecular Weight

233.24 g/mol

InChI Key

FKENQMMABCRJMK-RITPCOANSA-N

FDA UNII

S4TF6I2330

A beta-lactamase inhibitor with very weak antibacterial action. The compound prevents antibiotic destruction of beta-lactam antibiotics by inhibiting beta-lactamases, thus extending their spectrum activity. Combinations of sulbactam with beta-lactam antibiotics have been used successfully for the therapy of infections caused by organisms resistant to the antibiotic alone.

Sulbactam is a beta Lactamase Inhibitor. The mechanism of action of sulbactam is as a beta Lactamase Inhibitor.

1 2D Structure

Sulbactam

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S,5R)-3,3-dimethyl-4,4,7-trioxo-46-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

2.1.2 InChI

InChI=1S/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1

2.1.3 InChI Key

FKENQMMABCRJMK-RITPCOANSA-N

2.1.4 Canonical SMILES

CC1(C(N2C(S1(=O)=O)CC2=O)C(=O)O)C

2.1.5 Isomeric SMILES

CC1([C@@H](N2[C@H](S1(=O)=O)CC2=O)C(=O)O)C

2.2 Other Identifiers

2.2.1 UNII

S4TF6I2330

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Btamaze

2. Combactam

3. Cp 45899

4. Cp-45899

5. Cp45899

6. Penicillanic Acid Sulfone

7. Sodium, Sulbactam

8. Sulbactam Sodium

9. Sulfone, Penicillanic Acid

2.3.2 Depositor-Supplied Synonyms

1. 68373-14-8

2. Sulbactam Acid

3. Betamaze

4. Penicillanic Acid Sulfone

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

6. Sulbactamum

7. Penicillanic Acid 1,1-dioxide

8. (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid 4,4-dioxide

9. Chembl403

10. Cp-45899

11. (2s,5r)-3,3-dimethyl-4,4,7-trioxo-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

12. Cp-45,899

13. Chebi:9321

14. S4tf6i2330

15. Sulbactam (inn)

16. 68373-14-8 (free Acid)

17. Nsc-759886

18. Sulbactam 100 Microg/ml In Acetonitrile

19. Sulbactam [inn]

20. Dsstox_cid_3605

21. (2s,5r)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

22. Dsstox_rid_77104

23. Dsstox_gsid_23605

24. 2,2-dimethyl-1,1-dioxidopenam-3alpha-carboxylic Acid

25. Cp-458992

26. Smr000387064

27. Cas-68373-14-8

28. Cp 45899

29. Sulbactam [inn:ban]

30. Sr-01000760610

31. Sulbactamum [inn-latin]

32. Mfcd00867005

33. Unii-s4tf6i2330

34. Sulbactam,(s)

35. (2s,5r)-3,3-dimethyl-4,4,7-trioxo-4?^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

36. 0rn

37. Einecs 269-878-2

38. Sulbactam [mi]

39. Sulbactam [vandf]

40. Ncgc00159487-06

41. Sulbactam; Sulbactam Acid

42. Sulbactam [mart.]

43. Sulbactam [usp-rs]

44. Sulbactam [who-dd]

45. Schembl47781

46. Mls001048859

47. Mls001304017

48. Sodium 1,1-dioxypenicillanate

49. Dtxsid1023605

50. Gtpl10769

51. Hms2090e07

52. Hms2269a12

53. Hms3651c06

54. Hms3715b09

55. Zinc897244

56. Bcp13271

57. Ex-a2000

58. Hy-b0334

59. Tox21_113642

60. Bbl033518

61. Bdbm50021954

62. S1958

63. Stk801889

64. Akos004119988

65. Tox21_113642_1

66. Ccg-221124

67. Db09324

68. Ks-5198

69. Nsc 759886

70. (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure 4,4-dioxid

71. Sulbactam, Analytical Reference Material

72. Ncgc00159336-02

73. Ncgc00159336-03

74. Ncgc00159336-05

75. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, (2s-cis)-

76. Ac-18973

77. Bs167314

78. S0868

79. Sultamicillin Impurity A [ep Impurity]

80. C07770

81. D08533

82. Ab00698109-06

83. Ab00698109-08

84. Ab00698109_09

85. 373s148

86. A836122

87. Q423393

88. Sr-01000760610-2

89. Sr-01000760610-3

90. Brd-k44133266-001-10-0

91. Z1563146038

92. Sulbactam, European Pharmacopoeia (ep) Reference Standard

93. Sulbactam, United States Pharmacopeia (usp) Reference Standard

94. (2s,5r)-2-carboxylato-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane4,4-dioxide

95. (2s,5r)-3,3-dimethyl-4,4,7-trioxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

96. (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid4,4-dioxide

97. 3,3-dimethyl-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic Acid

98. Sulbactam For Peak Identification, European Pharmacopoeia (ep) Reference Standard

99. (2s,5r)-3,3-dimethyl-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic Acid

100. (2s,5r)-3,3-dimethyl-4,4,7-tris(oxidanylidene)-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid

101. (2s,5r)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo-[3.2.0]heptane-2-carboxylic Acid 4,4-dioxide

102. (2s,5r)?-?3,3-?dimethyl-?7-?oxo-?4-?thia-?1-?azabicyclo[3.2.0]?heptane-?2-?carboxylic Acid 4,4-dioxide

103. (s)-3,3-dimethyl-7-(r)-oxo-4,4-dioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic Acid

104. 3,3-dimethyl-4,4,7-trioxo-4lambda*6*-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic Acid (sulbactam)

105. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-,4,4-dioxide, (2s, Cis)

106. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid,3,3-dimethyl-7-oxo-, 4,4-dioxide, (2s,5r)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₈H₁₁NO₅S
Molecular Weight	233.24 g/mol
XLogP3	-1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	1
Exact Mass	233.03579362 g/mol
Monoisotopic Mass	233.03579362 g/mol
Topological Polar Surface Area	100 Å²
Heavy Atom Count	15
Formal Charge	0
Complexity	446
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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

Sulbactam is currently available in combination products with ampicillin. Within this formulation it is indicated for the treatment of infections due to susceptible strains of the designated microorganisms in the conditions listed below. Skin and Skin Structure Infections caused by beta-lactamase producing strains of Staphylococcus aureus, Escherichia coli, Klebsiella spp. (including K. pneumoniae), Proteus mirabilis, Bacteroides fragilis, Enterobacter spp., and Acinetobacter calcoaceticus. Intra-Abdominal Infections caused by beta-lactamase producing strains of Escherichia coli, Klebsiella spp. (including K. pneumoniae), Bacteroides spp. (including B. fragilis), and Enterobacter spp. Gynecological Infections caused by beta-lactamase producing strains of Escherichia coli, and Bacteroides spp. (including B. fragilis).

FDA Label

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

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

beta-Lactamase Inhibitors

Endogenous substances and drugs that inhibit or block the activity of BETA-LACTAMASES. (See all compounds classified as beta-Lactamase Inhibitors.)

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

SULBACTAM

5.2.2 FDA UNII

S4TF6I2330

5.2.3 Pharmacological Classes

Mechanisms of Action [MoA] - beta Lactamase Inhibitors

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01C - Beta-lactam antibacterials, penicillins

J01CG - Beta-lactamase inhibitors

J01CG01 - Sulbactam

5.4 Absorption, Distribution and Excretion

Absorption

Peak serum concentrations are reached almost immediately following a 15-minute intravenous infusion of sulbactam + ampicillin. Mean peak serum levels for sulbactam range from 48 to 88 mcg/mL following intravenous administration of 2000 mg of ampicillin plus 1000 mg sulbactam. After an intramuscular injection of 1000 mg ampicillin plus 500 mg sulbactam, peak sulbactam serum levels ranging from 6 to 24 mcg/mL are attained.

Route of Elimination

Approximately 75 to 85% of both ampicillin and sulbactam are excreted unchanged in the urine during the first 8 hours after administration.

Volume of Distribution

Penetration of both ampicillin and sulbactam into cerebrospinal fluid in the presence of inflamed meninges has been demonstrated after IV administration.

5.5 Biological Half-Life

~1 hr

5.6 Mechanism of Action

Sulbactam is an irreversible inhibitor of -lactamase; by binding and inhibiting -lactamase produced by bacterial cells, sulbactam is thereby able to prevent it from reducing antibiotic activity. Although sulbactam alone possesses little useful antibacterial activity, except against the Neisseriaceae, whole organism studies have shown that sulbactam restores ampicillin activity against beta-lactamase producing strains. In particular, sulbactam has good inhibitory activity against the clinically important plasmid mediated beta-lactamases most frequently responsible for transferred drug resistance. The presence of sulbactam in formulations with ampicillin effectively extends the antibacterial spectrum of ampicillin to include many bacteria normally resistant to it and to other beta-lactam antibacterials. Thus, products with ampicillin + sulbactam possess the properties of a broad-spectrum antibacterial and a beta-lactamase inhibitor.

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API Reference Price

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