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Cefpiramide

Synopsis, Chemistry

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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

Cefpiramide

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 Formula	C₂₅H₂₄N₈O₇S₂
Molecular Weight	612.6 g/mol
XLogP3	-0.1
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	9
Exact Mass	612.12093748 g/mol
Monoisotopic Mass	612.12093748 g/mol
Topological Polar Surface Area	259 Å²
Heavy Atom Count	42
Formal Charge	0
Complexity	1270
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	1

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.