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    Also known as: 26973-24-0, Ceftezol, Ceftezolum, Ceftezole [inn], 2z86syp11w, (6r,7r)-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-3-(1,3,4-thiadiazol-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
    Molecular Formula
    C13H12N8O4S3
    Molecular Weight
    440.5  g/mol
    InChI Key
    DZMVCVMFETWNIU-LDYMZIIASA-N
    FDA UNII
    2Z86SYP11W
    Ceftezole Sodium
    Ceftezole is a semisynthetic first-generation cephalosporin with antibacterial activity. Ceftezole binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. 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

    Ceftezole Sodium

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6R,7R)-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-3-(1,3,4-thiadiazol-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C13H12N8O4S3/c22-7(1-20-4-14-18-19-20)16-8-10(23)21-9(12(24)25)6(2-26-11(8)21)3-27-13-17-15-5-28-13/h4-5,8,11H,1-3H2,(H,16,22)(H,24,25)/t8-,11-/m1/s1
    2.1.3 InChI Key
    DZMVCVMFETWNIU-LDYMZIIASA-N
    2.1.4 Canonical SMILES
    C1C(=C(N2C(S1)C(C2=O)NC(=O)CN3C=NN=N3)C(=O)O)CSC4=NN=CS4
    2.1.5 Isomeric SMILES
    C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)CN3C=NN=N3)C(=O)O)CSC4=NN=CS4
    2.2 Other Identifiers
    2.2.1 UNII
    2Z86SYP11W
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Ceftezol

    2. Ceftezol, Sodium Salt

    3. Ceftezole Sodium

    4. Celoslin

    5. Demethylcefazolin

    6. Falomesin

    2.3.2 Depositor-Supplied Synonyms

    1. 26973-24-0

    2. Ceftezol

    3. Ceftezolum

    4. Ceftezole [inn]

    5. 2z86syp11w

    6. (6r,7r)-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-3-(1,3,4-thiadiazol-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    7. J01db12

    8. Ceftezole (inn)

    9. Demethylcefazolin

    10. (6r,7r)-8-oxo-7-[(1h-tetrazol-1-ylacetyl)amino]-3-[(1,3,4-thiadiazol-2-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    11. Demethyl Cefazolin

    12. (6r,7r)-8-oxo-7-(2-(1h-tetrazol-1-yl)acetamido)-3-((1,3,4-thiadiazol-2-ylthio)methyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

    13. Cg-b 3 Q

    14. Ncgc00182064-02

    15. Ceftezol [inn-spanish]

    16. Ceftezolum [inn-latin]

    17. Unii-2z86syp11w

    18. Ceftezole [mi]

    19. Ceftezole [who-dd]

    20. Mls006010107

    21. Schembl147529

    22. Chembl1697829

    23. Dtxsid0022771

    24. Chebi:135716

    25. Bcp12070

    26. Hy-n7095

    27. Zinc3830473

    28. Mfcd00274176

    29. S5289

    30. Akos037643294

    31. Ccg-269124

    32. Db13821

    33. As-13011

    34. Smr004701245

    35. Cs-0077833

    36. D07656

    37. 973c240

    38. A818761

    39. J-016638

    40. Q5057295

    41. (6r,7r)-3-((1,3,4-thiadiazol-2-ylthio)methyl)-7-(2-(1h-tetrazol-1-yl)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    42. (6r,7r)-8-oxo-7-[[1-oxo-2-(1-tetrazolyl)ethyl]amino]-3-[(1,3,4-thiadiazol-2-ylthio)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    43. (6r,7r)-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-3-(1,3,4-thiadiazol-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;ceftezole

    44. (6r,7r)-8-oxo-7-[2-(1h-tetrazol-1-yl)acetamido]-3-[(1,3,4-thiadiazol-2-ylsulfanyl)methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    45. 7-[2-(1h-tetrazol-1-yl)acetamido]-3-[(1,3,4-thiadiazol-2-ylsulfanyl)methyl]-3,4-didehydrocepham-4-carboxylic Acid

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 440.5 g/mol
    Molecular Formula C13H12N8O4S3
    XLogP3-0.7
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count7
    Exact Mass440.01436441 g/mol
    Monoisotopic Mass440.01436441 g/mol
    Topological Polar Surface Area235 Ų
    Heavy Atom Count28
    Formal Charge0
    Complexity709
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Anti-Bacterial Agents

    Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

    4.2 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01D - Other beta-lactam antibacterials

    J01DB - First-generation cephalosporins

    J01DB12 - Ceftezole

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