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Synopsis

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Chemistry

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Also known as: Cefadole, 34444-01-4, Cephamandole, Cefamandol, Cephadole, Cefamandolum

Molecular Formula

C₁₈H₁₈N₆O₅S₂

Molecular Weight

462.5 g/mol

InChI Key

OLVCFLKTBJRLHI-AXAPSJFSSA-N

FDA UNII

5CKP8C2LLI

Semisynthetic wide-spectrum cephalosporin with prolonged action, probably due to beta-lactamase resistance. It is used also as the nafate.

1 2D Structure

Cefamandole

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7R)-7-[[(2R)-2-hydroxy-2-phenylacetyl]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/C18H18N6O5S2/c1-23-18(20-21-22-23)31-8-10-7-30-16-11(15(27)24(16)12(10)17(28)29)19-14(26)13(25)9-5-3-2-4-6-9/h2-6,11,13,16,25H,7-8H2,1H3,(H,19,26)(H,28,29)/t11-,13-,16-/m1/s1

2.1.3 InChI Key

OLVCFLKTBJRLHI-AXAPSJFSSA-N

2.1.4 Canonical SMILES

CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)NC(=O)C(C4=CC=CC=C4)O)SC2)C(=O)O

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)O)SC2)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

5CKP8C2LLI

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cephamandole

2. Compound 83405

2.3.2 Depositor-Supplied Synonyms

1. Cefadole

2. 34444-01-4

3. Cephamandole

4. Cefamandol

5. Cephadole

6. Cefamandolum

7. L-cefamandole

8. Compound 83405

9. Chebi:3480

10. (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-carboxylic Acid

11. 5ckp8c2lli

12. (6r,7r)-7-{[(2r)-2-hydroxy-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-carboxylic Acid

13. Compound-83405

14. (6r,7r)-7-[[(2r)-2-hydroxy-2-phenylacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

15. J01dc03

16. Kefdole

17. 7-d-mandelamido-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-3-cephem-4-carboxylic Acid

18. Kefamandol

19. Mancef

20. (6r,7r)-7-((r)-2-hydroxy-2-phenylacetamido)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

21. 7-[(2-hydroxy-2-phenylacetyl)amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

22. 30034-03-8

23. Unii-5ckp8c2lli

24. Cefamandol [inn-spanish]

25. Cefamandole (usan/inn)

26. Cefamandolum [inn-latin]

27. Free Form

28. Cefamandole [usan:inn:ban]

29. Einecs 252-030-0

30. Brn 0598510

31. Cefamandole [mi]

32. Prestwick0_000747

33. Prestwick1_000747

34. Prestwick2_000747

35. Prestwick3_000747

36. Cefamandole [inn]

37. Cefamandole [usan]

38. Epitope Id:141490

39. Cefamandole [vandf]

40. Cefamandole [mart.]

41. Chembl1146

42. Schembl37287

43. Bspbio_000734

44. Cefamandole [who-dd]

45. Spbio_002673

46. Bpbio1_000808

47. Dtxsid7022750

48. Gtpl12210

49. Hy-b1128

50. Zinc3830394

51. Bdbm50350468

52. Akos025401365

53. Ac-1294

54. Cs-4724

55. Db01326

56. (6r,7r)-7-[[(2r)-2-hydroxy-2-phenyl-acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

57. (6r,7r)-7-{[(2r)-2-hydroxy-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-carboxylic Acid

58. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((hydroxyphenylacetyl)amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6alpha,7beta(r*)))-

59. 7beta-[(2r)-2-hydroxy-2-phenylacetamido]-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylic Acid

60. C06879

61. D02344

62. 444c014

63. Cefamandole, Antibiotic For Culture Media Use Only

64. Q2601530

65. W-106736

66. Brd-k27130738-236-03-4

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

68. (6r,7r)-7-[(2r)-2-hydroxy-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-carboxylic Acid

69. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((hydroxyphenylacetyl)amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6.alpha.,7.beta.(r*)))-

70. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 7-[[(2r)-2-hydroxy-2-phenylacetyl]amino]-3-[[(1-methyl-1h-tetrazol-5-yl)thio]methyl]-8-oxo-, (6r,7r)-

71. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 7-[[(2r)-2-hydroxy-2-phenylacetyl]amino]-3-[[(1-methyl-1h-tetrazol-5-yl)thio]methyl]-8-oxo-, 6r,7r)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₈N₆O₅S₂
Molecular Weight	462.5 g/mol
XLogP3	-0.9
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	7
Exact Mass	462.07801004 g/mol
Monoisotopic Mass	462.07801004 g/mol
Topological Polar Surface Area	201 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	777
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 the treatment of serious infections caused by susceptible strains of microorganisms.

5 Pharmacology and Biochemistry

5.1 Pharmacology

The parenteral prodrug formate ester cefamandole nafate is a broad-spectrum cephalosporin antibiotic. The bactericidal action of cefamandole results from inhibition of cell-wall synthesis. Cephalosporins have in vitro activity against a wide range of gram-positive and gram-negative organisms.

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

J01DC - Second-generation cephalosporins

J01DC03 - Cefamandole

5.4 Biological Half-Life

The half-life after an intravenous dose is 32 minutes; after intramuscular administration, the half-life is 60 minutes.

5.5 Mechanism of Action

Like all beta-lactam antibiotics, cefamandole binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefamandole interferes with an autolysin inhibitor.

FDF Dossiers