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    Cefmetazole

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    GLOBAL SALES INFORMATION

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

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    2D Structure
    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

    2D Structure

    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 Weight 471.5 g/mol
    Molecular Formula C15H17N7O5S3
    XLogP3-0.6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count9
    Exact Mass471.04533019 g/mol
    Monoisotopic Mass471.04533019 g/mol
    Topological Polar Surface Area239 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity818
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.

    5.5 Metabolism/Metabolites

    No appreciable metabolism.

    5.6 Biological Half-Life

    1.50 ±0.14 hours

    5.7 Mechanism of Action

    The bactericidal activity of cefmetazole results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).