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Also known as: 30034-03-8, Cefamandole sodium salt, Sodium cefamandole, Cefamandole (sodium), Cefamandole sodium [jan], Iy6234odvr

Molecular Formula

C₁₈H₁₇N₆NaO₅S₂

Molecular Weight

484.5 g/mol

InChI Key

OJMNTWPPFNMOCJ-CFOLLTDRSA-M

FDA UNII

IY6234ODVR

Cefamandole Sodium is the sodium salt form of cefamandole, a 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 Sodium Salt

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;(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-carboxylate

2.1.2 InChI

InChI=1S/C18H18N6O5S2.Na/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);/q;+1/p-1/t11-,13-,16-;/m1./s1

2.1.3 InChI Key

OJMNTWPPFNMOCJ-CFOLLTDRSA-M

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-].[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)O)SC2)C(=O)[O-].[Na+]

2.2 Other Identifiers

2.2.1 UNII

IY6234ODVR

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 30034-03-8

2. Cefamandole Sodium Salt

3. Sodium Cefamandole

4. Cefamandole (sodium)

5. Cefamandole Sodium [jan]

6. Iy6234odvr

7. Mls000069575

8. Chebi:34614

9. Kefdole

10. Nsc-758169

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

12. Smr000058843

13. Cefamandole Sodium (jan)

14. Cephamandole Sodium

15. Unii-iy6234odvr

16. Cefamandole Sodium [usp:jan]

17. Prestwick_23

18. Ncgc00017101-01

19. Einecs 250-009-0

20. Kefdole (tn)

21. Cas-30034-03-8

22. Opera_id_59

23. Cephamandole Sodium Salt

24. Sodium;(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-carboxylate

25. Cefamandolesodiumsalt

26. Dsstox_cid_25579

27. Dsstox_rid_80975

28. Dsstox_gsid_45579

29. Chembl1360024

30. Dtxsid2045579

31. Hy-b1128a

32. Hms1570e16

33. Hms2097e16

34. Hms2235i03

35. Cefamandole Sodium [mart.]

36. Cefamandole Sodium [who-dd]

37. Tox21_110777

38. Akos015967200

39. Akos024288585

40. Cs-5991

41. Nsc 758169

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

43. C-2463

44. D02191

45. Q27116182

46. Cefamandole Sodium Salt, Antibiotic For Culture Media Use Only

47. 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-(6a,7b(r*)))-, Monosodium Salt

48. 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*)))-, Monosodium Salt

49. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-mandelamido-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, Monosodium Salt, D-

50. 7beta-(d-mandel-amido)-3-(1-methyl-1h-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic Acid Sodium Salt

51. 7beta-(d-mandelamido)-3-(1-methyl-1h-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic Acid Sodium Salt

52. Sodium (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-carboxylate

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

2.4 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₇N₆NaO₅S₂
Molecular Weight	484.5 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	7
Exact Mass	484.05995429 g/mol
Monoisotopic Mass	484.05995429 g/mol
Topological Polar Surface Area	204 Å²
Heavy Atom Count	32
Formal Charge	0
Complexity	783
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