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Synopsis

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Chemistry

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Also known as: 56796-20-4, Cefmetazolo, Cefmetazolum, Cefmetazolum [inn-latin], Cefmetazolo [inn-spanish], (6r,7s)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Molecular Formula

C₁₅H₁₇N₇O₅S₃

Molecular Weight

471.5 g/mol

InChI Key

SNBUBQHDYVFSQF-HIFRSBDPSA-N

FDA UNII

3J962UJT8H

A semisynthetic cephamycin antibiotic with a broad spectrum of activity against both gram-positive and gram-negative microorganisms. It has a high rate of efficacy in many types of infection and to date no severe side effects have been noted.

1 2D Structure

Cefmetazole

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7S)-7-[[2-(cyanomethylsulfanyl)acetyl]amino]-7-methoxy-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/C15H17N7O5S3/c1-21-14(18-19-20-21)30-6-8-5-29-13-15(27-2,17-9(23)7-28-4-3-16)12(26)22(13)10(8)11(24)25/h13H,4-7H2,1-2H3,(H,17,23)(H,24,25)/t13-,15+/m1/s1

2.1.3 InChI Key

SNBUBQHDYVFSQF-HIFRSBDPSA-N

2.1.4 Canonical SMILES

CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O

2.1.5 Isomeric SMILES

CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)CSCC#N)OC)SC2)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

3J962UJT8H

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cefmetazole Monosodium Salt

2. Cefmetazole Sodium

3. Cefmetazon

4. Cs 1170

5. Cs-1170

6. Cs1170

7. Monosodium Salt, Cefmetazole

8. Salt, Cefmetazole Monosodium

9. Sodium, Cefmetazole

10. U 72791a

11. U-72791a

12. U72791a

13. Zefazone

2.3.2 Depositor-Supplied Synonyms

1. 56796-20-4

2. Cefmetazolo

3. Cefmetazolum

4. Cefmetazolum [inn-latin]

5. Cefmetazolo [inn-spanish]

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

7. Chebi:3489

8. U-72791

9. 3j962ujt8h

10. (6r,7s)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

11. (6r,7s)-7-(2-((cyanomethyl)thio)acetamido)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

12. 56796-20-4 (free)

13. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((((cyanomethyl)thio)acetyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-cis)-

14. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,7-[[[(cyanomethyl)thio]acetyl]amino]-7-methoxy-3-[[(1-methyl-1h-tetrazol-5-yl)thio]methyl]-8-oxo-, (6r,7s)-

15. Cs 1170

16. Skf 83088

17. U 72791

18. Cefmetazole (usp/inn)

19. Einecs 260-384-2

20. Brn 0634647

21. Unii-3j962ujt8h

22. Cefmetazole [usan:usp:inn]

23. Cefmetazolesodium

24. Cefmetazole [mi]

25. Prestwick0_000700

26. Prestwick1_000700

27. Prestwick2_000700

28. Prestwick3_000700

29. Cefmetazole [inn]

30. Cefmetazole [usan]

31. Epitope Id:116204

32. Cefmetazole [vandf]

33. Cefmetazole [mart.]

34. Lopac0_000266

35. Bspbio_000859

36. Cefmetazole [usp-rs]

37. Cefmetazole [who-dd]

38. Schembl147832

39. Spbio_002780

40. Bpbio1_000945

41. Cefmetazole Sodium [jan]

42. Chembl1201195

43. Dtxsid7022756

44. Gtpl12215

45. Cefmetazole [usp Impurity]

46. Cefmetazole [usp Monograph]

47. Bcp11998

48. Hy-b1595

49. Zinc3830417

50. Bdbm50350471

51. Mfcd00865068

52. Akos015896219

53. Db00274

54. Sdccgsbi-0050254.p002

55. (6r,7s)-7-({[(cyanomethyl)thio]acetyl}amino)-7-(methyloxy)-3-{[(1-methyl-1h-tetrazol-5-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

56. (6r,7s)-7-(2-((cyanomethyl)thio)acetamido)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thiomethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, Sodium Salt

57. Ac-13154

58. Bs-42476

59. 2,6-difluoro-4-methoxyacetophenone

60. Cs-0013513

61. C08103

62. D00910

63. A831178

64. J-700159

65. Q5057238

66. (6r,7s)-7-({[(cyanomethyl)sulfanyl]acetyl}amino)-7-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia

67. (6r,7s)-7-(2-(cyanomethylthio)acetamido)-7-methoxy-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,7s)-7-[[2-(cyanomethylthio)-1-oxoethyl]amino]-7-methoxy-3-[[(1-methyl-5-tetrazolyl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

69. (6r,7s)-7-[2-(cyanomethylsulfanyl)ethanoylamino]-7-methoxy-3-[(1-methyl-1,2,3,4-tetrazol-5-yl)sulfanylmethyl]-8-oxidanylidene-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

70. (6r,7s)-7-{2-[(cyanomethyl)sulfanyl]acetamido}-7-methoxy-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

71. 7beta-{[(cyanomethyl)sulfanyl]acetamido}-7alpha-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}ceph-3-em-4-carboxylic Acid

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₇N₇O₅S₃
Molecular Weight	471.5 g/mol
XLogP3	-0.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	9
Exact Mass	471.04533019 g/mol
Monoisotopic Mass	471.04533019 g/mol
Topological Polar Surface Area	239 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	818
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

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of infections caused by susceptible organisms.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Cefmetazole is a second-generation cephalosporin. The cephalosporins are bactericidal drugs with both gram-positive and gram-negative activity. They inhibit bacterial cell wall synthesis in a way similar to the penicillins. Cefmetazole is more active than 1st-generation cephalosporins against indole-positive Proteus, Serratia, anaerobic gram-negative bacilli (including B. fragilis), and some E. coli, Klebsiella, and P. mirabilis, but is less active than cefoxitin or cefotetan against most gram-negative bacilli.

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

J01DC09 - Cefmetazole

5.4 Absorption, Distribution and Excretion

Absorption

Bioavailability is approximately 100% following intramuscular injection.