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    2D Structure
    Also known as: Cefixime, 97164-56-2, 79350-37-1, Cefixime(e)-form, (e)-cefixime, Cefixime anhydrous, (e)-
    Molecular Formula
    C16H15N5O7S2
    Molecular Weight
    453.5  g/mol
    InChI Key
    OKBVVJOGVLARMR-VINNURBNSA-N
    FDA UNII
    U7RWT9J78O
    A third-generation cephalosporin antibiotic that is stable to hydrolysis by beta-lactamases.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
    2.1.2 InChI
    InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9+/t10-,14-/m1/s1
    2.1.3 InChI Key
    OKBVVJOGVLARMR-VINNURBNSA-N
    2.1.4 Canonical SMILES
    C=CC1=C(N2C(C(C2=O)NC(=O)C(=NOCC(=O)O)C3=CSC(=N3)N)SC1)C(=O)O
    2.1.5 Isomeric SMILES
    C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N/OCC(=O)O)/C3=CSC(=N3)N)SC1)C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    U7RWT9J78O
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Cefixime

    2. Cefixime Anhydrous

    3. Cefixime Trihydrate

    4. Fk 027

    5. Fk-027

    6. Fk027

    7. Fr 17027

    8. Fr-17027

    9. Fr17027

    2.3.2 Depositor-Supplied Synonyms

    1. Cefixime

    2. 97164-56-2

    3. 79350-37-1

    4. Cefixime(e)-form

    5. (e)-cefixime

    6. Cefixime Anhydrous, (e)-

    7. U7rwt9j78o

    8. Cfix

    9. (6r,7r)-7-(((2e)-2-(2-amino-4-thiazolyl)-2-((carboxymethoxy)imino)acetyl)amino)-3-ethenyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

    10. (6r,7r)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    11. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2e)-2-(2-amino-4-thiazolyl)-2-((carboxymethoxy)imino)acetyl)amino)-3-ethenyl-8-oxo-, (6r,7r)-

    12. Cefixime Impurity D

    13. Unii-u7rwt9j78o

    14. (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    15. Cefiximetrihydrate

    16. Prestwick2_000462

    17. Epitope Id:116227

    18. Schembl24946

    19. Schembl49534

    20. Chembl427069

    21. Bdbm88962

    22. Chebi:93248

    23. Gtpl10898

    24. Cid_56642849

    25. Hms1569m06

    26. (6r,7r)-7-((z)-2-(2-aminothiazol-4-yl)-2-((carboxymethoxy)imino)acetamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    27. Zinc4468778

    28. Ncgc00185001-01

    29. (e)-cefixime (cefixime Ep Impurity D)

    30. Q163901

    31. J-005196

    32. J-501698

    33. Brd-k04993501-001-01-9

    34. [6r-[6alpha,7beta(e)]]-7-[[(2-amino-4-thiazolyl)[(car

    35. (6r,7r)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;hydrate

    36. (6r,7r)-7-[[(2e)-2-(2-amino-4-thiazolyl)-2-(carboxymethoxyimino)-1-oxoethyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;hydrate

    37. (6r,7r)-7-[[(2e)-2-(2-aminothiazol-4-yl)-2-(carboxymethyloximino)acetyl]amino]-8-keto-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;hydrate

    38. (6r,7r)-7-[[(2e)-2-(2-azanyl-1,3-thiazol-4-yl)-2-(2-hydroxy-2-oxoethyloxyimino)ethanoyl]amino]-3-ethenyl-8-oxidanylidene-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;hydrate

    39. (6r,7r)-7-[[(2z)-2-(2-amino-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene -2-carboxylic Acid

    40. (6r,7r,e)-7-(2-(2-aminothiazol-4-yl)-2-(carboxymethoxyimino)acetamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    2.4 Create Date
    2005-11-20
    3 Chemical and Physical Properties
    Molecular Weight 453.5 g/mol
    Molecular Formula C16H15N5O7S2
    XLogP3-0.7
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count8
    Exact Mass453.04129018 g/mol
    Monoisotopic Mass453.04129018 g/mol
    Topological Polar Surface Area238 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity861
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    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 FDA Pharmacological Classification
    4.2.1 Pharmacological Classes
    Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]
    4.3 ATC Code

    J - Antiinfectives for systemic use

    J01 - Antibacterials for systemic use

    J01D - Other beta-lactam antibacterials

    J01DD - Third-generation cephalosporins

    J01DD08 - Cefixime