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Chemistry

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Also known as: Cefapirin sodium, 24356-60-3, Sodium cefapirin, Cefadyl, Cephapirin sodium salt, Bl-p 1322
Molecular Formula
C17H16N3NaO6S2
Molecular Weight
445.4  g/mol
InChI Key
VGEOUKPOQQEQSX-OALZAMAHSA-M
FDA UNII
431LFF7I7J

Cephapirin Sodium
Cephalosporin antibiotic, partly plasma-bound, that is effective against gram-negative and gram-positive organisms.
1 2D Structure

Cephapirin Sodium

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
2.1.2 InChI
InChI=1S/C17H17N3O6S2.Na/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11;/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25);/q;+1/p-1/t13-,16-;/m1./s1
2.1.3 InChI Key
VGEOUKPOQQEQSX-OALZAMAHSA-M
2.1.4 Canonical SMILES
CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)[O-].[Na+]
2.1.5 Isomeric SMILES
CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)[O-].[Na+]
2.2 Other Identifiers
2.2.1 UNII
431LFF7I7J
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Bl P 1322

2. Bl-p 1322

3. Blp 1322

4. Brisfirina

5. Cfaloject

6. Cefadyl

7. Cefapirin

8. Cephapirin

9. Cephapirin Monosodium Salt

10. Cephapirin, Sodium

11. Monosodium Salt, Cephapirin

12. Salt, Cephapirin Monosodium

13. Sodium Cephapirin

2.3.2 Depositor-Supplied Synonyms

1. Cefapirin Sodium

2. 24356-60-3

3. Sodium Cefapirin

4. Cefadyl

5. Cephapirin Sodium Salt

6. Bl-p 1322

7. Cefatrexyl

8. Ambrocef

9. Cefatrex

10. Sodium Cephapirin

11. Bl-p-1322

12. Cefaloject

13. Sodium 7-(pyrid-4-ylthioacetamido)cephalosporanate

14. 431lff7i7j

15. Chebi:3545

16. Cephatrexil

17. Nsc-179171

18. Cefa Lak

19. Brisfirina

20. Blp 1322

21. Cefapirin Sodium (jan)

22. Cela-lak/today

23. Dsstox_cid_25574

24. Dsstox_rid_80971

25. Dsstox_gsid_45574

26. Monosodium (6r,7r)-3-(hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate Acetate (ester)

27. Cefapirin Sodium [jan]

28. Cephatrexyl

29. Brisporin

30. Bristocef

31. Cefapirina Sodica

32. Cefadyl Im/iv

33. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-((acetyloxy)methyl)-8-oxo-7-(((4-pyridylthio)acetyl)amino)-, Monosodium Salt, (6r-trans)-

34. Sodium (6r-trans)-3-(acetoxymethyl)-8-oxo-7-((4-pyridylthio)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

35. Sodium (6r-trans)-3-(acetoxymethyl)-8-oxo-7-[(4-pyridylthio)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

36. Sodium;(6r,7r)-3-(acetyloxymethyl)-8-oxo-7-[(2-pyridin-4-ylsulfanylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

37. Cefapirin Sodium Salt

38. Cefa-lak (veterinary)

39. Cephapirin Sodium [usan]

40. Antibiotic Bl-p 1322

41. Unii-431lff7i7j

42. 356c603

43. Cephapirin Sodium [usan:usp]

44. Prestwick_27

45. Ncgc00017093-01

46. Cefadyl (tn)

47. Einecs 246-194-2

48. Cas-24356-60-3

49. Nsc 179171

50. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,3-[(acetyloxy)methyl]-8-oxo-7-[[(4-pyridinylthio)acetyl]amino]-,monosodium Salt, (6r,7r)-

51. 7-(alpha-(4-pyridylthio)acetamido)cephalosporanic Acid Sodium Salt

52. Cephapirin Sodium (usp)

53. Cephapirin Sodium, >=96%

54. Schembl64430

55. 3-[(acetyloxy)methyl]-8-oxo-7-{(4-pyridinylthio)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Monosodium Salt

56. Spectrum1500167

57. Chembl1201043

58. Dtxsid7045574

59. Hms500c04

60. Cefapirin Sodium [mart.]

61. Cefapirin Sodium [who-dd]

62. Hms1570l03

63. Hms1920k13

64. Hms2091a16

65. Cephapirin Sodium [usp-rs]

66. Cephapirin Sodium Salt [mi]

67. Tox21_110772

68. Ccg-38912

69. Cefapirin Sodium, Analytical Standard

70. Akos024282660

71. Cephapirin Sodium [green Book]

72. Tox21_110772_1

73. Cefapirin Sodium [ep Monograph]

74. Cephapirin Sodium [orange Book]

75. Cephapirin Sodium [usp Impurity]

76. Cephapirin Sodium [usp Monograph]

77. Ncgc00093735-01

78. Ncgc00162116-04

79. (7r,7ar)-3-(acetyloxymethyl)-6-oxo-7-(2-(4-pyridylthio)acetylamino)-2h,7h-azet Idino[2,1-b]1,3-thiazine-4-carboxylic Acid, Sodium Salt

80. As-83522

81. Eu-0100279

82. C 8270

83. C08101

84. C74249

85. D00908

86. A924266

87. Q27106128

88. Cefapirin Sodium, European Pharmacopoeia (ep) Reference Standard

89. 7-(.alpha.-(4-pyridylthio)acetamido)cephalosporanic Acid Sodium Salt

90. Cephapirin Sodium, United States Pharmacopeia (usp) Reference Standard

91. 5-thia-1-azabicyclo(4,2,0)oct-2-ene-2-carboxylic Acid, 3-(hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-, Acetate (ester), Monosodium Salt

92. Monosodium (6r,7r)-3-(hydroxymethyl)-8-oxo-7-(2-(4-pyridylthio)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate Acetate

93. Sodium (6r,7r)-3-(acetoxymethyl)-8-oxo-7-(2-(pyridin-4-ylthio)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

94. Sodium (6r,7r)-3-[(acetyloxy)methyl]-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

2.4 Create Date
2008-02-05
3 Chemical and Physical Properties
Molecular Weight 445.4 g/mol
Molecular Formula C17H16N3NaO6S2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count8
Exact Mass445.03782187 g/mol
Monoisotopic Mass445.03782187 g/mol
Topological Polar Surface Area179 Ų
Heavy Atom Count29
Formal Charge0
Complexity713
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
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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