Cefazedone

Synopsis, Chemistry

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Also known as: 56187-47-4, Refosporen, Refosporene, Cefazedona, Cefazedonum, (6r,7r)-7-[[2-(3,5-dichloro-4-oxopyridin-1-yl)acetyl]amino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Molecular Formula

C₁₈H₁₅Cl₂N₅O₅S₃

Molecular Weight

548.4 g/mol

InChI Key

VTLCNEGVSVJLDN-MLGOLLRUSA-N

FDA UNII

7Y86X0D799

Cefazedone is a semisynthetic first-generation cephalosporin with antibacterial activity. Cefazedone binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.

1 2D Structure

Cefazedone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7R)-7-[[2-(3,5-dichloro-4-oxopyridin-1-yl)acetyl]amino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C18H15Cl2N5O5S3/c1-7-22-23-18(33-7)32-6-8-5-31-16-12(15(28)25(16)13(8)17(29)30)21-11(26)4-24-2-9(19)14(27)10(20)3-24/h2-3,12,16H,4-6H2,1H3,(H,21,26)(H,29,30)/t12-,16-/m1/s1

2.1.3 InChI Key

VTLCNEGVSVJLDN-MLGOLLRUSA-N

2.1.4 Canonical SMILES

CC1=NN=C(S1)SCC2=C(N3C(C(C3=O)NC(=O)CN4C=C(C(=O)C(=C4)Cl)Cl)SC2)C(=O)O

2.1.5 Isomeric SMILES

CC1=NN=C(S1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)CN4C=C(C(=O)C(=C4)Cl)Cl)SC2)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

7Y86X0D799

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 7-(2-(3,5-dichloro-4-oxo-1- Pyridyl)acetamido)-3-(5-methyl-1,3,4-thiadiazol- 2-ylthiomethyl)-3-cephem-4-carboxylic Acid

2. Cefazedone Sodium

3. Cefazedone, Monosodium Salt

4. Emd 30 087

5. Emd30087

6. Refosporen

7. Refosporin

2.3.2 Depositor-Supplied Synonyms

1. 56187-47-4

2. Refosporen

3. Refosporene

4. Cefazedona

5. Cefazedonum

6. (6r,7r)-7-[[2-(3,5-dichloro-4-oxopyridin-1-yl)acetyl]amino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

7. Cefazedone (inn)

8. Emd-30087

9. 7y86x0d799

10. (6r,7r)-7-(2-(3,5-dichloro-4-oxo-1(4h)-pyridyl)acetamido)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)-oct-2-ene-2-carboxylic Acid

11. Cefazedone [inn]

12. Cefazedone [inn:ban]

13. Cefazedonum [inn-latin]

14. Cefazedona [inn-spanish]

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

16. Refosporin Sodium Salt

17. Cefazedone, Sodium Salt

18. Brn 1097746

19. Cefazedon

20. Cefazedone Acid

21. Unii-7y86x0d799

22. Refosporen;cefazedonum

23. Nsc304118

24. Cefazedone [mi]

25. Cefazedone (*sodium Salt*)

26. Cefazedone [who-dd]

27. Refosporin (*sodium Salt*)

28. Schembl49523

29. Chembl2107636

30. Gtpl12203

31. Dtxsid50204733

32. Chebi:131731

33. Zinc1567521

34. S4874

35. Ccg-269995

36. Db13778

37. (6r,7r)-7-[[2-(3,5-dichloro-4-oxo-1-pyridyl)acetyl]amino]-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

38. (6r-trans)7-(((3,5-dichloro-4-oxo-1(4h)-pyridinyl)acetyl)amino)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oxy-2-ene-2-carbox Ylic Acid

39. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((3,5-dichloro-4-oxo-1(4h)-pyridinyl)acetyl)amino)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-, (6r-trans)-

40. As-75724

41. Hy-121144

42. Cs-0079538

43. D07237

44. D95160

45. 187c474

46. A936727

47. Q5057222

48. (6r,7r)-7-(2-(3,5-dichloro-4-oxopyridin-1(4h)-yl)acetamido)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid

49. (6r,7r)-7-[2-(3,5-dichloro-4-oxopyridin-1(4h)-yl)acetamido]-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

50. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((2-(3,5-dichloro-4-oxo-1(4h)-pyridinyl)acetyl)amino)-3-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)-8-oxo-, (6r,7r)-

51. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 7-[[(3,5-dichloro-4-oxo-1(4h)-pyridinyl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-, Monosodium Salt, (6r-trans)-

52. 7-{[3,5-dichloro-4-oxopyridin-1(4h)-yl]acetamido}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-3,4-didehydrocepham-4-carboxylic Acid

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₅Cl₂N₅O₅S₃
Molecular Weight	548.4 g/mol
XLogP3	1.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	7
Exact Mass	546.9612375 g/mol
Monoisotopic Mass	546.9612375 g/mol
Topological Polar Surface Area	212 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	984
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1