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Also known as: Penicillin g sodium salt, 69-57-8, Benzylpenicillin sodium, Crystapen, Benzylpenicillin sodium salt, American penicillin

Molecular Formula

C₁₆H₁₇N₂NaO₄S

Molecular Weight

356.4 g/mol

InChI Key

FCPVYOBCFFNJFS-LQDWTQKMSA-M

FDA UNII

YS5LY7JF4N

A penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It has also been used as an experimental convulsant because of its actions on GAMMA-AMINOBUTYRIC ACID mediated synaptic transmission.

1 2D Structure

Benzylpenicillin Sodium

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C16H18N2O4S.Na/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);/q;+1/p-1/t11-,12+,14-;/m1./s1

2.1.3 InChI Key

FCPVYOBCFFNJFS-LQDWTQKMSA-M

2.1.4 Canonical SMILES

CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)[O-])C.[Na+]

2.1.5 Isomeric SMILES

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CC=C3)C(=O)[O-])C.[Na+]

2.2 Other Identifiers

2.2.1 UNII

YS5LY7JF4N

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Benpen

2. Benzylpenicillin

3. Benzylpenicillin Potassium

4. Coliriocilina

5. Crystapen

6. Or-pen

7. Parcillin

8. Pekamin

9. Pengesod

10. Penibiot

11. Penicilina G Llorente

12. Penicillin G

13. Penicillin G Jenapharm

14. Penicillin G Potassium

15. Penicillin Grnenthal

16. Penilevel

17. Peniroger

18. Pfizerpen

19. Sodiopen

20. Sodipen

21. Sodium Benzylpenicillin

22. Sodium Penicillin

23. Unicilina

24. Ursopen

25. Van-pen-g

2.3.2 Depositor-Supplied Synonyms

1. Penicillin G Sodium Salt

2. 69-57-8

3. Benzylpenicillin Sodium

4. Crystapen

5. Benzylpenicillin Sodium Salt

6. American Penicillin

7. Pencillin G Sodium

8. Sodium Benzylpenicillinate

9. Monosodium Benzylpenicillin

10. Benzylpenicillinic Acid Sodium Salt

11. Sodium Penicillin G

12. Ethacillin

13. Monocillin

14. Penicillinum

15. Penicillin G Sodium, Crystalline

16. Penicillin Sodium

17. Sodium Penicillin

18. Benzyl Penicillin Sodium

19. Sodium Benzylpenicillinoate

20. Sodium Penicillin Ii

21. Ys5ly7jf4n

22. Novocillin

23. Penilaryn

24. Veticillin

25. Penicillin G Sodium [usp]

26. Sodium Benzylpenicillin

27. 69-57-8 (sodium)

28. Kesso-pen

29. Pen-a-brasive

30. Sodium Benzylpenicillin G

31. Chebi:51765

32. Sugracillin Sodium Salt

33. Nsc-402815

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

35. Mycofarm

36. Penicillin-g, Monosodium Salt

37. Penicillin G Sodium (usp)

38. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)-, (2s-(2alpha,5alpha,6beta))-, Monosodium Salt

39. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-, Monosodium Salt

40. Penicillin G, Sodium

41. Ok 431

42. Sodium Benzylpenicyllinate

43. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-((2-phenylacetyl)amino)- (2s,5r,6r)-, Sodium Salt (1:1)

44. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)-(2s,5r,6r)-, Monosodium Salt

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

46. Sodium 6-(phenylacetamido)penicillanate

47. Einecs 200-710-2

48. Unii-ys5ly7jf4n

49. Nsc 402815

50. Mfcd00069666

51. 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]- (2s,5r,6r)-, Sodium Salt(1:1)

52. Benzylpenicillinum Natricum

53. Penicillin G Sodium (tn)

54. Penicillinum [hpus]

55. Chembl1126

56. Schembl34218

57. Dtxsid6040581

58. Benzyl Penicillin Potassium

59. Hms1571g18

60. Hms2098g18

61. Hms3715g18

62. Hy-b1463

63. Penicillin G Sodium [vandf]

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

65. S4160

66. Penicillin G Sodium [usp-rs]

67. Akos015961217

68. Penicillin G Sodium Salt [mi]

69. Benzylpenicillin Sodium [mart.]

70. Ccg-221078

71. Cs-7971

72. Benzylpenicillin Sodium [who-dd]

73. Benzylpenicillin Sodium [who-ip]

74. Cas-69-57-8

75. Ncgc00017015-01

76. Penicillin G Sodium Salt, ~1650 U/mg

77. Tetrabromobisphenoladiglycidylether

78. Ac-13436

79. As-80974

80. E706

81. Penicillin G Sodium [orange Book]

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

83. Penicillin G Sodium [usp Monograph]

84. Penicillin G Sodium Salt, 96.0-102.0%

85. Benzylpenicillin Sodium [ep Impurity]

86. P1770

87. Penicillin G Sodium Salt, Cell Culture Grade

88. Sw197252-3

89. Benzylpenicillin Sodium [ep Monograph]

90. C76205

91. D05408

92. P-1200

93. Benzylpenicillinum Natricum [who-ip Latin]

94. Q27122736

95. F0001-2583

96. Pencillin G Sodium Salt, Antibiotic For Culture Media Use Only

97. Sodium 2,2-dimethyl-6beta-(phenylacetamido)penam-3alpha-carboxylate

98. Benzylpenicillin Sodium, European Pharmacopoeia (ep) Reference Standard

99. Penicillin G Sodium Salt, Powder, Bioreagent, Suitable For Cell Culture

100. Penicillin G Sodium, United States Pharmacopeia (usp) Reference Standard

101. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)-, (2s-(2.alpha.,5.alpha.,6.beta.))-, Monosodium Salt

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

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₇N₂NaO₄S
Molecular Weight	356.4 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	356.08067248 g/mol
Monoisotopic Mass	356.08067248 g/mol
Topological Polar Surface Area	115 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	536
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	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Penicillin g sodium
PubMed Health	Penicillin G Sodium (Injection)
Drug Classes	Antibiotic
Drug Label	Penicillin G sodium for Injection, USP is sterile penicillin G sodium powder for reconstitution. It is an antibacterial agent intended for intravenous or intramuscularly use.Chemically, penicillin G sodium is designated 4-Thia-1-azabicyclo(3.2.0)-hep...
Active Ingredient	Penicillin g sodium
Dosage Form	Injectable
Route	Intramuscular, intravenous
Strength	5,000,000 units/vial
Market Status	Prescription
Company	Sandoz

2 of 2
Drug Name	Penicillin g sodium
PubMed Health	Penicillin G Sodium (Injection)
Drug Classes	Antibiotic
Drug Label	Penicillin G sodium for Injection, USP is sterile penicillin G sodium powder for reconstitution. It is an antibacterial agent intended for intravenous or intramuscularly use.Chemically, penicillin G sodium is designated 4-Thia-1-azabicyclo(3.2.0)-hep...
Active Ingredient	Penicillin g sodium
Dosage Form	Injectable
Route	Intramuscular, intravenous
Strength	5,000,000 units/vial
Market Status	Prescription
Company	Sandoz

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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Penicillins [CS]; Penicillin-class Antibacterial [EPC]

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