Cefamandole Nafate

Synopsis, Chemistry

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Also known as: 42540-40-9, Cephamandole nafate, Cefamandol nafato, Kefadol, Mandokef, O-formylcefamandole sodium

Molecular Formula

C₁₉H₁₇N₆NaO₆S₂

Molecular Weight

512.5 g/mol

InChI Key

ICZOIXFFVKYXOM-YCLOEFEOSA-M

FDA UNII

8HDO7941DO

Cefamandole Nafate is the sodium salt form of cefamandole formyl ester. Cefamandole nafate is a pro-drug that is hydrolyzed by plasma esterases to produce cefamandole, a semi-synthetic beta-lactam, second-generation cephalosporin antibiotic with bactericidal activity. Cefamandole binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall. 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

Cefamandole Nafate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;(6R,7R)-7-[[(2R)-2-formyloxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

2.1.2 InChI

InChI=1S/C19H18N6O6S2.Na/c1-24-19(21-22-23-24)33-8-11-7-32-17-12(16(28)25(17)13(11)18(29)30)20-15(27)14(31-9-26)10-5-3-2-4-6-10;/h2-6,9,12,14,17H,7-8H2,1H3,(H,20,27)(H,29,30);/q;+1/p-1/t12-,14-,17-;/m1./s1

2.1.3 InChI Key

ICZOIXFFVKYXOM-YCLOEFEOSA-M

2.1.4 Canonical SMILES

CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)NC(=O)C(C4=CC=CC=C4)OC=O)SC2)C(=O)[O-].[Na+]

2.1.5 Isomeric SMILES

CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)[C@@H](C4=CC=CC=C4)OC=O)SC2)C(=O)[O-].[Na+]

2.2 Other Identifiers

2.2.1 UNII

8HDO7941DO

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cefamandole Nafate, Monosodium Salt, (6r-(6alpha,7beta(r*)))-isomer

2. Cefamandole Nafate, Monosodium Salt, 14c-labeled, (6r-(6alpha,7beta,(r*)))-isomer

3. Mandol

2.3.2 Depositor-Supplied Synonyms

1. 42540-40-9

2. Cephamandole Nafate

3. Cefamandol Nafato

4. Kefadol

5. Mandokef

6. O-formylcefamandole Sodium

7. Sodium O-formylcefamandole

8. Cemandil Sodium Salt

9. Cefam

10. Cefamandole Nafate Sodium

11. 8hdo7941do

12. Chebi:3481

13. Cefamandole Formate Sodium Salt

14. Cefaseptolo

15. Lampomandol

16. Bergacef

17. Mandolsan

18. Neocefal

19. Pavecef

20. Cedol

21. Cefamandole Nafate [usan]

22. Ncgc00183035-01

23. Lilly 106223

24. Cefamandol Nafato [spanish]

25. Unii-8hdo7941do

26. Kefandol

27. Cemandil Sodium

28. Einecs 255-877-4

29. Mandol (tn)

30. Mfcd00864877

31. Nsc 299588

32. Cefamandole Nafate [usan:usp:inn:ban]

33. Cefamandole Formate Sodium

34. Cefamandole Nafate, 97%

35. Cefamandole Nafate (usp)

36. Dsstox_cid_2751

37. Chembl1618

38. Dsstox_rid_76715

39. Dsstox_gsid_22751

40. Schembl181311

41. Cefamandole Nafate [mi]

42. Dtxsid2022751

43. Cefamandole Nafate [vandf]

44. Cefamandole Nafate [mart.]

45. Cefamandole Nafate [usp-rs]

46. Cefamandole Nafate [who-dd]

47. Hy-b1166

48. Tox21_113487

49. Akos015895550

50. Akos015961133

51. Ac-1642

52. Ccg-269787

53. Cs-4768

54. Gs-3575

55. Cefamandole Nafate [orange Book]

56. Cefamandole Nafate [ep Monograph]

57. Cefamandole Nafate [usp Impurity]

58. As-12360

59. Cas-42540-40-9

60. C-2464

61. C08102

62. D00909

63. Q27106102

64. Cefamandole Nafate, Antibiotic For Culture Media Use Only

65. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((formyloxy)phenylacetyl)amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, Monosodium Salt, (6r-(6.alpha.,7.beta.(r*)))

66. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((formyloxy)phenylacetyl)amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, Monosodium Salt, (6r-(6alpha,7beta(r*)))-

67. Sodium (6r,7r)-7-((r)-2-(formyloxy)-2-phenylacetamido)-3-((1-methyl-1h-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

68. Sodium (6r,7r)-7-[(2r)-2-(formyloxy)-2-phenylacetamido]-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-carboxylate

69. Sodium (6r,7r)-7-[[(2r)-2-formyloxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

70. Sodium (6r,7r)-7-{[(2r)-2-(formyloxy)-2-phenylacetyl]amino}-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

71. Sodium (6r,7r)-7-{[(2r)-2-(formyloxy)-2-phenylacetyl]amino}-3-{[(1-methyl-1h-tetrazol-5-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

72. Sodium (6r-(6alpha,7beta(r*)))-7-(((formyloxy)phenylacetyl)amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

73. Sodium 7beta-[(2r)-2-(formyloxy)-2-phenylacetamido]-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylate

74. Sodium(6r,7r)-7-(r)-mandelamido-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate Formate(ester)

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₇N₆NaO₆S₂
Molecular Weight	512.5 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	9
Exact Mass	512.05486891 g/mol
Monoisotopic Mass	512.05486891 g/mol
Topological Polar Surface Area	210 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	844
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	2