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    Cefotetan

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    DIGITAL CONTENT

    GLOBAL SALES INFORMATION

    MARKET PLACE

    REF. STANDARDS & IMPURITIES

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    2D Structure
    Also known as: 69712-56-7, Cefotetanum, Apacef, Cefotetanum [inn-latin], Ici 156834, Ici-156834
    Molecular Formula
    C17H17N7O8S4
    Molecular Weight
    575.6  g/mol
    InChI Key
    SRZNHPXWXCNNDU-RHBCBLIFSA-N
    FDA UNII
    48SPP0PA9Q
    A semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms.
    Cefotetan is a Cephalosporin Antibacterial.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6R,7S)-7-[[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietane-2-carbonyl]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/C17H17N7O8S4/c1-23-16(20-21-22-23)34-4-5-3-33-15-17(32-2,14(31)24(15)7(5)11(29)30)19-9(26)13-35-12(36-13)6(8(18)25)10(27)28/h13,15H,3-4H2,1-2H3,(H2,18,25)(H,19,26)(H,27,28)(H,29,30)/t13?,15-,17+/m1/s1
    2.1.3 InChI Key
    SRZNHPXWXCNNDU-RHBCBLIFSA-N
    2.1.4 Canonical SMILES
    CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)(NC(=O)C4SC(=C(C(=O)N)C(=O)O)S4)OC)SC2)C(=O)O
    2.1.5 Isomeric SMILES
    CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@](C3=O)(NC(=O)C4SC(=C(C(=O)N)C(=O)O)S4)OC)SC2)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    48SPP0PA9Q
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Apacef

    2. Apatef

    3. Cefotan

    4. Cefotetan Disodium

    5. Cefotetan Disodium Salt

    6. Ceftotan

    7. Disodium Salt, Cefotetan

    8. Disodium, Cefotetan

    9. Ici 156834

    10. Ici-156834

    11. Ici156834

    12. Salt, Cefotetan Disodium

    13. Ym 09330

    14. Ym-09330

    15. Ym09330

    2.3.2 Depositor-Supplied Synonyms

    1. 69712-56-7

    2. Cefotetanum

    3. Apacef

    4. Cefotetanum [inn-latin]

    5. Ici 156834

    6. Ici-156834

    7. Ici 156,834

    8. 48spp0pa9q

    9. Mls002153829

    10. Chebi:3499

    11. Ici-156,834

    12. Ym 09330

    13. Nsc-760045

    14. (6r,7s)-7-({[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl}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

    15. Smr001233197

    16. (6r,7s)-7-(4-(carbamoylcarboxymethylene)-1,3-dithiethane-2-carboxamido)-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

    17. 7beta-({[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl}amino)-7alpha-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-3,4-didehydrocepham-4-carboxylic Acid

    18. Cefotetan Acid

    19. (6r,7s)-7-[[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    20. Unii-48spp0pa9q

    21. Cefotetan [usan:usp:inn:ban]

    22. Ncgc00016914-01

    23. Einecs 274-093-3

    24. Cas-69712-56-7

    25. Ici156834

    26. Brn 1208088

    27. Cefotetan [inn]

    28. Cefotetan [jan]

    29. Cefotetan [mi]

    30. Cefotetan [usan]

    31. Prestwick0_000473

    32. Prestwick1_000473

    33. Prestwick2_000473

    34. Prestwick3_000473

    35. Cefotetan [vandf]

    36. Dsstox_cid_2762

    37. Cefotetan [mart.]

    38. Cefotetan [who-dd]

    39. Dsstox_rid_76720

    40. Dsstox_gsid_22762

    41. Schembl61376

    42. Bspbio_000606

    43. (6r,7s)-7-(4-(carbamoylcarboxymethylene)-1,3-dithiethane-2-carboxamido)-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

    44. Cid_53025

    45. Spbio_002545

    46. Cefotetan (jp17/usp/inn)

    47. Bpbio1_000668

    48. Chembl474579

    49. Cefotetan [usp Impurity]

    50. Dtxsid1022762

    51. Bdbm80643

    52. Gtpl10936

    53. Cefotetan [usp Monograph]

    54. Hms1569o08

    55. Hms2096o08

    56. Hms2234c15

    57. Hms3713o08

    58. Amy28799

    59. Bcp10745

    60. Hy-n6670

    61. Zinc3830441

    62. Tox21_110681

    63. Mfcd00864983

    64. Akos015896100

    65. Ac-2141

    66. Ccg-220473

    67. Db01330

    68. Nsc 760045

    69. Ncgc00016914-06

    70. Ncgc00179507-01

    71. (6r,7s)-4-((2-carboxy-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-7-yl)carbamoyl)-1,3-dithietane-delta(sup 2,alpha)-malonamic Acid

    72. (6r,7s)-7-[[[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]carbonyl]amino]-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

    73. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl)carbonyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6alpha,7alpha))-

    74. As-56133

    75. Ab00513847

    76. Cs-0092723

    77. C06886

    78. D00260

    79. Cefotetan, Antibiotic For Culture Media Use Only

    80. 712c567

    81. A836615

    82. Sr-01000842155

    83. Q2602246

    84. Sr-01000842155-3

    85. W-104601

    86. (6r,7s)-4-((2-carboxy-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-7-yl)carbamoyl)-1,3-dithietane-.delta.(sup 2,.alpha.)-malonamic Acid

    87. (6r,7s)-7-(4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietane-2-carboxamido)-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

    88. (6r,7s)-7-[[[4-(2-amino-1-carboxy-2-oxoethylidene)-1,3-dithietan-2-yl]-oxomethyl]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

    89. (6r,7s)-7-[[4-(1-amino-3-hydroxy-1,3-dioxopropan-2-ylidene)1,3-dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    90. (6r,7s)-7-[[4-(2-amino-1-carboxy-2-keto-ethylidene)-1,3-dithietane-2-carbonyl]amino]-8-keto-7-methoxy-3-[[(1-methyltetrazol-5-yl)thio]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    91. (6r,7s)-7-[[4-[1-azanyl-3-oxidanyl-1,3-bis(oxidanylidene)propan-2-ylidene]-1,3-dithietan-2-yl]carbonylamino]-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

    92. Disodium 7-[[4-(2-amino-1-carboxylato-2-oxo-ethylidene)-1,3-dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

    2.4 Create Date
    2005-08-01
    3 Chemical and Physical Properties
    Molecular Weight 575.6 g/mol
    Molecular Formula C17H17N7O8S4
    XLogP30.1
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count15
    Rotatable Bond Count9
    Exact Mass575.00214522 g/mol
    Monoisotopic Mass575.00214522 g/mol
    Topological Polar Surface Area321 Ų
    Heavy Atom Count36
    Formal Charge0
    Complexity1090
    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 NameCefotetan
    PubMed HealthCefotetan (Injection)
    Drug ClassesAntibiotic
    Drug LabelCEFOTAN (cefotetan disodium for injection) and CEFOTAN (cefotetan injection) in Galaxy * plastic container (PL 2040) as cefotetan disodium are sterile, semisynthetic, broad-spectrum, beta-lactamase resistant, cephalosporin (cephamycin) antibiotics...
    Active IngredientCefotetan disodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
    Market StatusPrescription
    CompanyFresenius Kabi Usa; West-ward Pharm

    2 of 2  
    Drug NameCefotetan
    PubMed HealthCefotetan (Injection)
    Drug ClassesAntibiotic
    Drug LabelCEFOTAN (cefotetan disodium for injection) and CEFOTAN (cefotetan injection) in Galaxy * plastic container (PL 2040) as cefotetan disodium are sterile, semisynthetic, broad-spectrum, beta-lactamase resistant, cephalosporin (cephamycin) antibiotics...
    Active IngredientCefotetan disodium
    Dosage FormInjectable
    RouteInjection
    Strengtheq 2gm base/vial; eq 10gm base/vial; eq 1gm base/vial
    Market StatusPrescription
    CompanyFresenius Kabi Usa; West-ward Pharm

    4.2 Drug Indication

    For prophylaxis and treatment of bacterial infections.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Cefotetan is a semisynthetic cephamycin antibiotic that is administered intravenously or intramuscularly. The drug is highly resistant to a broad spectrum of beta-lactamases and is active against a wide range of both aerobic and anaerobic gram-positive and gram-negative microorganisms.

    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
    CEFOTETAN
    5.3.2 FDA UNII
    48SPP0PA9Q
    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

    J01DC05 - Cefotetan

    5.5 Absorption, Distribution and Excretion

    Route of Elimination

    No active metabolites of cefotetan have been detected; however, small amounts (less than 7%) of cefotetan in plasma and urine may be converted to its tautomer, which has antimicrobial activity similar to the parent drug. In normal patients, from 51% to 81% of an administered dose of Cefotetan is excreted unchanged by the kidneys over a 24 hour period, which results in high and prolonged urinary concentrations.

    Volume of Distribution

    10.4 L [elderly patients (greater than 65 years) with normal renal function]

    10.3 L [healthy volunteers (aged 25 to 28 years)]

    Clearance

    1.8 +/- 0.1 L/h [elderly patients with normal renal function (.65 years)]

    1.8 +/- 0.3 L/h [healthy volunteers (aged 25 to 28 years)]

    5.6 Metabolism/Metabolites

    No active metabolites of cefotetan have been detected; however, small amounts (less than 7%) of cefotetan in plasma and urine may be converted to its tautomer, which has antimicrobial activity similar to the parent drug.

    5.7 Biological Half-Life

    In volunteers with reduced renal function, the plasma half-life of cefotetan is prolonged

    5.8 Mechanism of Action

    The bactericidal action of cefotetan results from inhibition of cell wall synthesis by binding and inhibiting the bacterial penicillin binding proteins which help in the cell wall biosynthesis.