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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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    11-Jan-2021
    30-Sep-2024
    KGS
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    Average Price (USD/KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

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    DOSAGE - INJECTABLE;INJECTION - EQ 2GM BASE/V...DOSAGE - INJECTABLE;INJECTION - EQ 2GM BASE/VIAL;EQ 250MG BASE/VIAL **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 50684

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    DOSAGE - INJECTABLE;INJECTION - EQ 36GM BASE/...DOSAGE - INJECTABLE;INJECTION - EQ 36GM BASE/VIAL;EQ 4.5GM BASE/VIAL **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 50684

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    DOSAGE - INJECTABLE;INJECTION - EQ 3GM BASE/V...DOSAGE - INJECTABLE;INJECTION - EQ 3GM BASE/VIAL;EQ 375MG BASE/VIAL **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 50684

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    DOSAGE - INJECTABLE;INJECTION - EQ 4GM BASE/V...DOSAGE - INJECTABLE;INJECTION - EQ 4GM BASE/VIAL;EQ 500MG BASE/VIAL **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

    USFDA APPLICATION NUMBER - 50684

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    DOSAGE - INJECTABLE;INJECTION - EQ 40MG BASE/...DOSAGE - INJECTABLE;INJECTION - EQ 40MG BASE/ML;EQ 5MG BASE/ML

    USFDA APPLICATION NUMBER - 50750

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    DOSAGE - INJECTABLE;INJECTION - EQ 4GM BASE/1...DOSAGE - INJECTABLE;INJECTION - EQ 4GM BASE/100ML;EQ 500MG BASE/100ML

    USFDA APPLICATION NUMBER - 50750

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    DOSAGE - INJECTABLE;INJECTION - EQ 60MG BASE/...DOSAGE - INJECTABLE;INJECTION - EQ 60MG BASE/ML;EQ 7.5MG BASE/ML

    USFDA APPLICATION NUMBER - 50750

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