Ampicillin Sodium

Synopsis, Chemistry

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Also known as: 200-708-1, 69-52-3, Ampicillin sodium salt, Sodium ampicillin, Citteral, Domicillin

Molecular Formula

C₁₆H₁₈N₃NaO₄S

Molecular Weight

371.4 g/mol

InChI Key

KLOHDWPABZXLGI-YWUHCJSESA-M

FDA UNII

JFN36L5S8K

Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic.

1 2D Structure

Ampicillin Sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C16H19N3O4S.Na/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8;/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23);/q;+1/p-1/t9-,10-,11+,14-;/m1./s1

2.1.3 InChI Key

KLOHDWPABZXLGI-YWUHCJSESA-M

2.1.4 Canonical SMILES

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

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

JFN36L5S8K

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Amcill

2. Aminobenzyl Penicillin

3. Aminobenzylpenicillin

4. Ampicillin

5. Ampicillin Trihydrate

6. Antibiotic Ks R1

7. Antibiotic Ks-r1

8. Ks-r1, Antibiotic

9. Omnipen

10. Penicillin, Aminobenzyl

11. Pentrexyl

12. Polycillin

13. Sodium, Ampicillin

14. Trihydrate, Ampicillin

15. Ukapen

2.3.2 Depositor-Supplied Synonyms

1. 200-708-1

2. 69-52-3

3. Ampicillin Sodium Salt

4. Sodium Ampicillin

5. Citteral

6. Domicillin

7. Penialmen

8. Ampicillin Natrium

9. Omnipen

10. Penbritin

11. Totacillin

12. Ampicillin (sodium)

13. Austrapen

14. Polycillin-n

15. Sodium D-(-)-alpha-aminobenzylpenicillin

16. Totacillin-n

17. Penbritin-s

18. Omnipen-n

19. Ampicillin (as Sodium)

20. Jfn36l5s8k

21. Mls000028726

22. D(-)-alpha-aminobenzylpenicillin Sodium Salt

23. Chebi:34535

24. Nsc-755864

25. Smr000059229

26. Monosodium D-(-)-6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

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

28. Ampicillinsodium

29. Binotal Sodium

30. Sodium Binotal

31. Principen/n

32. Amcill-s

33. Alpen-n

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

35. Sodium P-50

36. Mfcd00064313

37. Pen A/n

38. Unii-jfn36l5s8k

39. Ampiplus Simplex

40. Viccillin (tn)

41. Prestwick_822

42. Ampicillin Sodium [usan:usp:jan]

43. Einecs 200-708-1

44. Ampicillinum Natricum

45. Omnipen-n (tn)

46. Ampicillin Sodium Salt, Cell Culture Grade

47. Opera_id_709

48. (2s,5r,6r)-6-[[(2r)-2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid Sodium Salt

49. Ampicillinsodiumsalt

50. Ampicillin Sodium, Sterile

51. Schembl40521

52. Spectrum1500123

53. Ampicillin Sodium [jan]

54. Ampicillin Sodium (jp17/usp)

55. Ampicillin Sodium [usan]

56. Chembl1200758

57. Hms501h08

58. Hy-b0522a

59. Ampicillin Sodium [vandf]

60. Dtxsid60988759

61. Ampicillin Sodium [mart.]

62. Hms1920c21

63. Hms2091i21

64. Hms2232j12

65. Ampicillin Sodium [usp-rs]

66. Ampicillin Sodium [who-dd]

67. Ampicillin Sodium [who-ip]

68. Ampicillin Sodium Salt [mi]

69. Ccg-39691

70. S3170

71. Akos015967315

72. Akos025147373

73. Ampicillin Sodium [green Book]

74. Ac-8806

75. Ampicillin Sodium [orange Book]

76. Nsc 755864

77. Ampicillin Sodium [ep Monograph]

78. Ampicillin Sodium [usp Monograph]

79. D-(-)-alpha-aminobenzylpenicillin &sdot

80. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, Monosodium Salt, (2s-(2alpha,5alpha,6beta(s*)))-

81. Ba166035

82. Monosodium (2s,5r,6r)-6-((r)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

83. D-(-)-a-aminobenzylpenicillin Sodium Salt

84. Ampicillin Sodium, Sterile [who-ip]

85. Ampicillinum Natricum [who-ip Latin]

86. Sw220219-1

87. A-7700

88. D02119

89. A836527

90. Ampicillin Sodium (non-injectable) [who-ip]

91. Q27116136

92. Ampicillin Sodium Salt, Antibiotic For Culture Media Use Only

93. Sodium 6beta-[(2r)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carboxylate

94. (2s,5r,6r)-6-[[(2r)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid, Sodium Salt (1:1)

95. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, Monosodium Salt, (2s-(2.alpha.,5.alpha.,6.beta.(s*)))-

96. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-, Sodium Salt, D-(-)-

97. 6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-,sodiumsalt,d-(-)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid

98. Sodium (2s-(2alpha,5alpha,6beta(s*)))-6-(aminophenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

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

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₈N₃NaO₄S
Molecular Weight	371.4 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	371.09157152 g/mol
Monoisotopic Mass	371.09157152 g/mol
Topological Polar Surface Area	141 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	568
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Ampicillin sodium
Drug Label	Ampicillin for Injection, USP the monosodium salt of [2S-[2,5,6(S*)]]-6- [(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-4thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, is a synthetic penicillin for intramuscular or intravenous use. The pha...
Active Ingredient	Ampicillin sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 2gm base/vial; eq 125mg base/vial; eq 500mg base/vial; eq 10gm base/vial; eq 250mg base/vial; eq 1gm base/vial
Market Status	Prescription
Company	Istituto Bio Ita Spa; Antibiotice; Hanford Gc; Acs Dobfar Spa; Aurobindo Pharma; Strides Arcolab; Sandoz; Agila Speclts

2 of 2
Drug Name	Ampicillin sodium
Drug Label	Ampicillin for Injection, USP the monosodium salt of [2S-[2,5,6(S*)]]-6- [(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-4thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, is a synthetic penicillin for intramuscular or intravenous use. The pha...
Active Ingredient	Ampicillin sodium
Dosage Form	Injectable
Route	Injection
Strength	eq 2gm base/vial; eq 125mg base/vial; eq 500mg base/vial; eq 10gm base/vial; eq 250mg base/vial; eq 1gm base/vial
Market Status	Prescription
Company	Istituto Bio Ita Spa; Antibiotice; Hanford Gc; Acs Dobfar Spa; Aurobindo Pharma; Strides Arcolab; Sandoz; Agila Speclts