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    Cefoxitin

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    GLOBAL SALES INFORMATION

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

    PharmaCompass
    $ API Ref.Price (USD/KG) : 441Xls

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    2D Structure
    Also known as: 35607-66-0, Mefoxin, Cefoxitinum, Rephoxitin, Cephoxitin, Cefoxitina
    Molecular Formula
    C16H17N3O7S2
    Molecular Weight
    427.5  g/mol
    InChI Key
    WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
    FDA UNII
    6OEV9DX57Y
    A semisynthetic cephamycin antibiotic resistant to beta-lactamase.
    Cefoxitin is a Cephalosporin Antibacterial.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6R,7S)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C16H17N3O7S2/c1-25-16(18-10(20)5-9-3-2-4-27-9)13(23)19-11(12(21)22)8(6-26-15(17)24)7-28-14(16)19/h2-4,14H,5-7H2,1H3,(H2,17,24)(H,18,20)(H,21,22)/t14-,16+/m1/s1
    2.1.3 InChI Key
    WZOZEZRFJCJXNZ-ZBFHGGJFSA-N
    2.1.4 Canonical SMILES
    COC1(C2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)CC3=CC=CS3
    2.1.5 Isomeric SMILES
    CO[C@@]1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)CC3=CC=CS3
    2.2 Other Identifiers
    2.2.1 UNII
    6OEV9DX57Y
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Cefoxitin Sodium

    2. Mfoxin

    3. Mefoxin

    4. Mefoxitin

    5. Mk 306

    6. Mk-306

    7. Mk306

    8. Sodium, Cefoxitin

    2.3.2 Depositor-Supplied Synonyms

    1. 35607-66-0

    2. Mefoxin

    3. Cefoxitinum

    4. Rephoxitin

    5. Cephoxitin

    6. Cefoxitina

    7. Cefoxitine

    8. Mefoxitin

    9. Ceftoxitin

    10. Cfx

    11. Cenomycin

    12. Chebi:209807

    13. Chembl996

    14. 6oev9dx57y

    15. J01dc01

    16. Dsstox_cid_2764

    17. Dsstox_rid_76721

    18. Dsstox_gsid_22764

    19. (6r,7s)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    20. (6r,7s)-3-(hydroxymethyl)-7-methoxy-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid Carbamate (ester)

    21. (6r,7s)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    22. (6r,7s)-3-((carbamoyloxy)methyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    23. Cas-35607-66-0

    24. Ncgc00183034-01

    25. Cefoxitine [inn-french]

    26. Cefoxitinum [inn-latin]

    27. Cefoxitina [inn-spanish]

    28. Unii-6oev9dx57y

    29. Cefoxotin

    30. Cefoxitin [usan:inn:ban]

    31. 4kow

    32. Mk306

    33. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-(((aminocarbonyl)oxy)methyl)-7-methoxy-8-oxo-7-((2-thienylacetyl)amino)-, (6r,7s)-

    34. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid, 3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-, (6r,7s)-

    35. Einecs 252-641-2

    36. Mfcd00072014

    37. Spectrum_001399

    38. Cefoxitin [inn]

    39. Cefoxitin [mi]

    40. Cefoxitin (usan/inn)

    41. Cefoxitin [usan]

    42. Prestwick0_000832

    43. Prestwick1_000832

    44. Prestwick2_000832

    45. Prestwick3_000832

    46. Spectrum2_000676

    47. Spectrum3_001491

    48. Spectrum4_000153

    49. Spectrum5_001145

    50. Cefoxitin [vandf]

    51. Epitope Id:116201

    52. C06887

    53. Cefoxitin [usp-rs]

    54. Cefoxitin [who-dd]

    55. Schembl15971

    56. Bspbio_000783

    57. Bspbio_003101

    58. Kbiogr_000626

    59. Kbioss_001879

    60. Divk1c_000576

    61. Spbio_000771

    62. Spbio_002704

    63. Bpbio1_000863

    64. Cefoxitin [orange Book]

    65. Dtxsid1022764

    66. Gtpl10937

    67. Kbio1_000576

    68. Kbio2_001879

    69. Kbio2_004447

    70. Kbio2_007015

    71. Kbio3_002601

    72. Ninds_000576

    73. Bcp09061

    74. Hy-b1825

    75. Zinc3830449

    76. Tox21_113009

    77. Bdbm50335563

    78. S5951

    79. Akos022185232

    80. Tox21_113009_1

    81. Db01331

    82. Ds-5384

    83. Idi1_000576

    84. Ncgc00093351-06

    85. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 3-(((aminocarbonyl)oxy)methyl)-7-methoxy-8-oxo-7-((2-thienylacetyl)amino)-, (6r-cis)-

    86. 73356-24-8

    87. Sbi-0051927.p002

    88. C3598

    89. Cs-0013876

    90. (6r,7r)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    91. (6r,7s)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    92. (6r,7s)-3-carbamoyloxymethyl-7-methoxy-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    93. (6r,7s)-4-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    94. (6s,7r)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    95. (6s,7r)-4-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    96. 3-carbamoyloxymethyl-7-methoxy-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    97. 3-carbamoyloxymethyl-7-methoxy-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Anion

    98. 3-carbamoyloxymethyl-7-methoxy-8-oxo-7-(2-thiophen-3-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Anion

    99. D02345

    100. 607c660

    101. A822898

    102. Q2353907

    103. (6r,7s)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    104. (6r,7s)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    105. (6r,7s)-3-(carbamoyloxymethyl)-7-methoxy-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;cefoxitin

    106. (6r,7s)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    107. (6r,7s)-3-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    108. (6r,7s)-3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2- Carboxylic Acid

    109. (6r,7s)-3-{[(aminocarbonyl)oxy]methyl}-7-(methyloxy)-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    110. (6r,7s)-4-[(carbamoyloxy)methyl]-7-methoxy-8-oxo-7-[(thiophen-2-enyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    111. 3-[(carbamoyloxy)methyl]-7alpha-methoxy-7beta-[(thiophen-2-yl)acetamido]-3,4-didehydrocepham-4-carboxylic Acid

    112. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-, (6r-cis)-

    113. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,3-[[(aminocarbonyl)oxy]methyl]-7-methoxy-8-oxo-7-[(2-thienylacetyl)amino]-,(6r,7s)-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 427.5 g/mol
    Molecular Formula C16H17N3O7S2
    XLogP30
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count8
    Exact Mass427.05079224 g/mol
    Monoisotopic Mass427.05079224 g/mol
    Topological Polar Surface Area202 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity744
    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 Information
    1 of 2  
    Drug NameCefoxitin
    PubMed HealthCefoxitin (Injection)
    Drug ClassesAntibiotic
    Drug LabelCefoxitin for Injection, USP contains cefoxitin sodium a semi-synthetic, broad-spectrum cephalosporin antibiotic for parenteral administration. It is derived from cephalosporin C, which is produced by Cephalosporium Acremonium. Its chemical name is s...
    Active IngredientCefoxitin sodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
    Market StatusPrescription
    CompanyAcs Dobfar; Hospira; Hikma Maple; Hikma Farmaceutica; Antibioticos Brasil

    2 of 2  
    Drug NameCefoxitin
    PubMed HealthCefoxitin (Injection)
    Drug ClassesAntibiotic
    Drug LabelCefoxitin for Injection, USP contains cefoxitin sodium a semi-synthetic, broad-spectrum cephalosporin antibiotic for parenteral administration. It is derived from cephalosporin C, which is produced by Cephalosporium Acremonium. Its chemical name is s...
    Active IngredientCefoxitin sodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
    Market StatusPrescription
    CompanyAcs Dobfar; Hospira; Hikma Maple; Hikma Farmaceutica; Antibioticos Brasil

    4.2 Drug Indication

    For the treatment of serious infections caused by susceptible strains microorganisms.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Cefoxitin is a cephamycin antibiotic often grouped with the second-generation cephalosporins. It is active against a broad range of gram-negative bacteria including anaerobes. The methoxy group in the 7a position provides cefoxitin with a high degree of stability in the presence of beta-lactamases, both penicillinases and cephalosporinases, of gram-negative bacteria.

    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 FDA Pharmacological Classification
    5.3.1 Active Moiety
    CEFOXITIN
    5.3.2 FDA UNII
    6OEV9DX57Y
    5.3.3 Pharmacological Classes
    Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]
    5.4 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01D - Other beta-lactam antibacterials

    J01DC - Second-generation cephalosporins

    J01DC01 - Cefoxitin

    5.5 Absorption, Distribution and Excretion

    Route of Elimination

    Approximately 85 percent of cefoxitin is excreted unchanged by the kidneys over a 6-hour period, resulting in high urinary concentrations. Cefoxitin passes into pleural and joint fluids and is detectable in antibacterial concentrations in bile.

    5.6 Metabolism/Metabolites

    Minimal (approximately 85 percent of cefoxitin is excreted unchanged by the kidneys over a 6-hour period).

    5.7 Biological Half-Life

    The half-life after an intravenous dose is 41 to 59 minutes.

    5.8 Mechanism of Action

    The bactericidal action of cefoxitin results from inhibition of cell wall synthesis.