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    Cefpiramide

    ACTIVE PHARMA INGREDIENTS

    REF. STANDARDS & IMPURITIES

    PharmaCompass
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    2D Structure
    Also known as: 70797-11-4, Cefpiramide acid, Cefpiramido, Cefpiramidum, Wy-44635, Wy-44,635
    Molecular Formula
    C25H24N8O7S2
    Molecular Weight
    612.6  g/mol
    InChI Key
    PWAUCHMQEXVFJR-PMAPCBKXSA-N
    FDA UNII
    P936YA152N
    Cefpiramide is a third-generation, semi-synthetic, beta-lactam cephalosporin antibiotic with antibacterial activity. Cefpiramide binds to penicillin-binding proteins (PBPs), transpeptidases that are responsible for crosslinking of peptidoglycan. By preventing crosslinking of peptidoglycan, cell wall integrity is lost and cell wall synthesis is halted.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6R,7R)-7-[[(2R)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1H-pyridine-3-carbonyl)amino]acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C25H24N8O7S2/c1-11-7-16(35)15(8-26-11)20(36)27-17(12-3-5-14(34)6-4-12)21(37)28-18-22(38)33-19(24(39)40)13(9-41-23(18)33)10-42-25-29-30-31-32(25)2/h3-8,17-18,23,34H,9-10H2,1-2H3,(H,26,35)(H,27,36)(H,28,37)(H,39,40)/t17-,18-,23-/m1/s1
    2.1.3 InChI Key
    PWAUCHMQEXVFJR-PMAPCBKXSA-N
    2.1.4 Canonical SMILES
    CC1=CC(=O)C(=CN1)C(=O)NC(C2=CC=C(C=C2)O)C(=O)NC3C4N(C3=O)C(=C(CS4)CSC5=NN=NN5C)C(=O)O
    2.1.5 Isomeric SMILES
    CC1=CC(=O)C(=CN1)C(=O)N[C@H](C2=CC=C(C=C2)O)C(=O)N[C@H]3[C@@H]4N(C3=O)C(=C(CS4)CSC5=NN=NN5C)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    P936YA152N
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Cefpiramide Sodium

    2. Cefpiramide, Sodium Salt

    3. Sm 1652

    4. Sm-1652

    5. Sumcefal

    2.3.2 Depositor-Supplied Synonyms

    1. 70797-11-4

    2. Cefpiramide Acid

    3. Cefpiramido

    4. Cefpiramidum

    5. Wy-44635

    6. Wy-44,635

    7. (6r,7r)-7-[[(2r)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1h-pyridine-3-carbonyl)amino]acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    8. Chebi:59213

    9. P936ya152n

    10. Nsc-759869

    11. Ncgc00167444-01

    12. Sm 1652

    13. Sm-1652

    14. (7r)-7-[[(2r)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1h-pyridine-3-carbonyl)amino]acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    15. (6r,7r)-7-((r)-2-(4-hydroxy-6-methylnicotinamido)-2-(4-hydroxyphenyl)acetamido)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    16. Wy 44,635

    17. Cefpiramidum [inn-latin]

    18. Cefpiramido [inn-spanish]

    19. Unii-p936ya152n

    20. Cefpiramide [usan:usp:inn]

    21. Wy 44635

    22. Cefpiramide (usp/inn)

    23. Cefpiramide [mi]

    24. Cefpiramide [inn]

    25. Cefpiramide [usan]

    26. Cefpiramide [mart.]

    27. Dsstox_cid_26630

    28. Dsstox_rid_81778

    29. Dsstox_gsid_46630

    30. Schembl49253

    31. Cefpiramide [usp-rs]

    32. Cefpiramide [who-dd]

    33. Chembl1201204

    34. Dtxsid6046630

    35. Gtpl12027

    36. Cefpiramide [usp Impurity]

    37. Hms3715h12

    38. Hy-b1354

    39. Zinc4215257

    40. Tox21_112448

    41. Mfcd00864893

    42. S5186

    43. Akos025311237

    44. Ccg-221235

    45. Db00430

    46. Nsc 759869

    47. Ncgc00167444-04

    48. (6r,7r)-7-((r)-2-(4-hydroxy-6-methylnicotinamido)-2-(p-hydroxyphenyl)acetamido)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

    49. As-14170

    50. Cas-70797-11-4

    51. Cs-0013097

    52. D03428

    53. 797c114

    54. Q4921174

    55. Brd-k92872987-001-02-9

    56. Cefpiramide Acid;cefpiramido;cefpiramidum;wy-44635;sm-1652

    57. (6r,7r)-7-((r)-2-(4-hydroxy-6-methylnicotinamido)-2-(4-hydroxyphenyl)acetamido)-3-((1-methyl-1h-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    58. (6r,7r)-7-[(2r)-2-[(4-hydroxy-6-methylpyridin-3-yl)formamido]-2-(4-hydroxyphenyl)acetamido]-3-{[(1-methyl-1h-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    59. (6r,7r)-7-{[(2r)-2-{[(4-hydroxy-6-methylpyridin-3-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetyl]amino}-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    60. (7r)-7-((r)-2-(4-hydroxy-6-methylnicotinamido)-2-(4-hydroxyphenyl)acetamido)-3-((1-methyl-1h-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    61. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((((4-hydroxy-6-methyl-3-pyridinyl)carbonyl)amino)(4-hydroxyphenyl)acetyl)amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6alpha,7beta(r*)))-

    62. 7beta-[(2r)-2-{[(4-hydroxy-6-methylpyridin-3-yl)carbonyl]amino}-2-(4-hydroxyphenyl)acetamido]-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-3,4-didehydrocepham-4-carboxylic Acid

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 612.6 g/mol
    Molecular Formula C25H24N8O7S2
    XLogP3-0.1
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count13
    Rotatable Bond Count9
    Exact Mass612.12093748 g/mol
    Monoisotopic Mass612.12093748 g/mol
    Topological Polar Surface Area259 Ų
    Heavy Atom Count42
    Formal Charge0
    Complexity1270
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For treatment of severe infections caused by susceptible bacteria such as P. aeruginosa.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Cefpiramide is a cephalosporin active against Pseudomonas aeruginosa. It has a broad spectrum of antibacterial activity. Cefpiramide works by inhibiting bacterial cell wall biosynthesis. The plasma half-lives of cefpiramide in rabbits, dogs, and rhesus monkeys were much longer than those of cefoperazone and cefazolin.

    5.2 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    5.3 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01D - Other beta-lactam antibacterials

    J01DD - Third-generation cephalosporins

    J01DD11 - Cefpiramide

    5.4 Absorption, Distribution and Excretion

    Absorption

    Rapidly absorbed following intramuscular injection.

    5.5 Biological Half-Life

    4.44 hours

    5.6 Mechanism of Action

    The bactericidal activity of cefpiramide results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).