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Chemistry

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Also known as: 59703-84-3, Pipracil, Piperacillin sodium salt, Sodium piperacillin, Piperacillin (sodium), Penmalin
Molecular Formula
C23H26N5NaO7S
Molecular Weight
539.5  g/mol
InChI Key
WCMIIGXFCMNQDS-IDYPWDAWSA-M
FDA UNII
M98T69Q7HP

Piperacillin Sodium
Semisynthetic, broad-spectrum, AMPICILLIN derived ureidopenicillin antibiotic proposed for PSEUDOMONAS infections. It is also used in combination with other antibiotics.
1 2D Structure

Piperacillin Sodium

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
sodium;(2S,5R,6R)-6-[[(2R)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)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/C23H27N5O7S.Na/c1-4-26-10-11-27(19(32)18(26)31)22(35)25-13(12-8-6-5-7-9-12)16(29)24-14-17(30)28-15(21(33)34)23(2,3)36-20(14)28;/h5-9,13-15,20H,4,10-11H2,1-3H3,(H,24,29)(H,25,35)(H,33,34);/q;+1/p-1/t13-,14-,15+,20-;/m1./s1
2.1.3 InChI Key
WCMIIGXFCMNQDS-IDYPWDAWSA-M
2.1.4 Canonical SMILES
CCN1CCN(C(=O)C1=O)C(=O)NC(C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)[O-].[Na+]
2.1.5 Isomeric SMILES
CCN1CCN(C(=O)C1=O)C(=O)N[C@H](C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)[O-].[Na+]
2.2 Other Identifiers
2.2.1 UNII
M98T69Q7HP
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ab Piperacillin

2. Ab-piperacillin

3. Cl 227193

4. Cl-227193

5. Cl227193

6. Curasan, Piperacillin

7. Monosodium Salt, Piperacillin

8. Pipcil

9. Pipera Hameln

10. Pipera-hameln

11. Piperacillin

12. Piperacillin Curasan

13. Piperacillin Fresenius

14. Piperacillin Hexal

15. Piperacillin Monosodium Salt

16. Piperacillin Ratiopharm

17. Piperacillin-ratiopharm

18. Pipercillin

19. Pipracil

20. Pipril

21. Salt, Piperacillin Monosodium

22. Sodium, Piperacillin

23. T 1220

24. T-1220

25. T1220

2.3.2 Depositor-Supplied Synonyms

1. 59703-84-3

2. Pipracil

3. Piperacillin Sodium Salt

4. Sodium Piperacillin

5. Piperacillin (sodium)

6. Penmalin

7. Piperacillin (as Sodium)

8. Mls000069533

9. Chebi:8233

10. M98t69q7hp

11. Cl 227,193

12. T-1220

13. Nsc-757277

14. Cl-227193

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

16. Smr000058579

17. Sodium (2s,5r,6r)-6-((r)-2-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate

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

19. Pentcillin

20. Pipracil Sterile

21. Unii-m98t69q7hp

22. 1-carboxamido)-2-phenylacetamido)-3,3-dimethyl-

23. Ccris 2591

24. Zosyn Sterile

25. Pentcillin (tn)

26. T 1220

27. Pipracil (tn)

28. Einecs 261-868-6

29. Mfcd00917471

30. Piperacillin Sodium [usan:usp:jan]

31. Prestwick_1028

32. Cl 227193

33. Opera_id_1140

34. Schembl34180

35. Mls002548888

36. Chembl1200820

37. Dtxsid6048965

38. Piperacillin Sodium [jan]

39. Piperacillin Sodium (jp17/usp)

40. Hms1570g12

41. Hms2097g12

42. Hms3259m09

43. Hms3714g12

44. Piperacillin Sodium [usan]

45. Piperacillin Sodium [vandf]

46. Hy-b1286

47. Cl227193

48. Piperacillin Sodium [who-dd]

49. S4222

50. Piperacillin Sodium Salt [mi]

51. Akos024464845

52. Ccg-220755

53. Cs-4894

54. Nc00477

55. Nsc 757277

56. Piperacillin Sodium [orange Book]

57. Piperacillin Sodium [ep Monograph]

58. Zosyn Component Piperacillin Sodium

59. Piperacillin Sodium [usp Monograph]

60. Piperacillin Sodium Salt, Penicillin Analog

61. P1774

62. Piperacillin Sodium Component Of Zosyn

63. Piperacillin Sodium Salt, Analytical Standard

64. C07361

65. D00466

66. Q-201585

67. Q27108010

68. 7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

69. Sodium (2s,5r,6r)-6-((r)-2-(4-ethyl-2,3-dioxopiperazine-

70. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-, Monosodium Salt, (2s-(2.alpha.,5.alpha.,6.beta.(s*)))

71. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-, Monosodium Salt, (2s-(2alpha,5alpha,6beta(s*)))

72. 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic Acid, 6-(((((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-, Monosodium Salt, (2s-(2alpha,5alpha,6beta(s*)))-

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

74. Sodium 6beta-{(2r)-2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido}-2,2-dimethylpenam-3alpha-carboxylate

2.4 Create Date
2008-02-05
3 Chemical and Physical Properties
Molecular Weight 539.5 g/mol
Molecular Formula C23H26N5NaO7S
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count8
Rotatable Bond Count6
Exact Mass539.14506364 g/mol
Monoisotopic Mass539.14506364 g/mol
Topological Polar Surface Area185 Ų
Heavy Atom Count37
Formal Charge0
Complexity989
Isotope Atom Count0
Defined Atom Stereocenter Count4
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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