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    CFIX

    PharmaCompass
    Xls

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    2D Structure
    Also known as: 79350-37-1, Cephoral, Cefixima, Cefiximum, Cefspan, Cefixime anhydrous
    Molecular Formula
    C16H15N5O7S2
    Molecular Weight
    453.5  g/mol
    InChI Key
    OKBVVJOGVLARMR-QSWIMTSFSA-N
    FDA UNII
    XZ7BG04GJX
    A third-generation cephalosporin antibiotic that is stable to hydrolysis by beta-lactamases.
    Cefixime anhydrous is a Cephalosporin Antibacterial.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (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
    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-QSWIMTSFSA-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
    XZ7BG04GJX
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Cefixime Anhydrous

    2. Cefixime Trihydrate

    3. Fk 027

    4. Fk-027

    5. Fk027

    6. Fr 17027

    7. Fr-17027

    8. Fr17027

    9. Suprax

    2.3.2 Depositor-Supplied Synonyms

    1. 79350-37-1

    2. Cephoral

    3. Cefixima

    4. Cefiximum

    5. Cefspan

    6. Cefixime Anhydrous

    7. Cefixim

    8. Cefiximum [latin]

    9. (-)-cefixim

    10. Oroken

    11. Cefixima [spanish]

    12. Suprax

    13. Fk-027

    14. Cl-284635

    15. Anhydrous Cefixime

    16. Fk 027

    17. Fr 17027

    18. Fr-17027

    19. Xz7bg04gjx

    20. Mls002222332

    21. Cefixoral

    22. Chebi:472657

    23. Cefixime (inn)

    24. Citropen

    25. Cfix

    26. (6r,7r)-7-({(2z)-2-(2-amino-1,3-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

    27. Smr001307271

    28. Unixime

    29. Cefixime [inn]

    30. Cl 284,635

    31. Necopen

    32. Denvar

    33. Tricef

    34. Unii-xz7bg04gjx

    35. Cefixime [usan:usp:inn:ban:jan]

    36. Brn 6025058

    37. Cefixime [mi]

    38. Cl 284635

    39. (6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7(sup 2)-(z)-(o-(carboxymethyl)oxime)trihydrate

    40. Prestwick3_000462

    41. Cefixime [who-dd]

    42. Chembl1541

    43. Schembl24945

    44. Bspbio_000564

    45. Bpbio1_000622

    46. Dtxsid7022754

    47. Bdbm84007

    48. Cid_5362065

    49. Hms2096m06

    50. Hms2234j21

    51. Hms3713m06

    52. (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

    53. (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

    54. Hy-b1381

    55. Mfcd00865020

    56. S4596

    57. Zinc12503147

    58. Akos015854940

    59. Akos015961135

    60. Ac-4350

    61. Ccg-220462

    62. Cs-4820

    63. Db00671

    64. Ncgc00179521-01

    65. Ncgc00179521-03

    66. (6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7(sup 2)-(z)-(o-(carboxymethyl)oxime) Trihydrate

    67. (6r,7r)-7-[-2-(2-amino-thiazol-4-yl)-2-carboxymethoxyimino-acetylamino]-8-oxo-3-vinyl-5-thia-1-aza-b

    68. (6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-{[(carboxymethyl)oxy]imino}acetyl]amino}-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    69. 7beta-{(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido}-3-ethenyl-3,4-didehydrocepham-4-carboxylic Acid

    70. Ab00513842

    71. 50c371

    72. A13697

    73. C-2469

    74. C06881

    75. D00258

    76. Cefixime, Antibiotic For Culture Media Use Only

    77. Sr-01000760706

    78. Sr-01000760706-4

    79. Brd-k71059170-001-02-5

    80. Brd-k71059170-001-08-2

    81. Q27290799

    82. (6r,7r)-7-((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

    83. (6r,7r)-7-[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    84. (6r,7r)-7-[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

    85. (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

    86. (6s,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

    87. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)((carboxymethoxy)imino)acetyl)amino)-3-ethenyl-8-oxo-, Trihydrate, (6r-(6alpha,7beta(z)))-

    88. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2z)-(2-amino-4-thiazolyl)((carboxymethoxy)imino)acetyl)amino)-3-ethenyl-8-oxo-, (6r,7r)-

    89. C04

    2.4 Create Date
    2005-08-08
    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 Drug and Medication Information
    4.1 Drug Indication

    For use in the treatment of the following infections when caused by susceptible strains of the designated microorganisms: (1) uncomplicated urinary tract infections caused by Escherichia coli and Proteus mirabilis, (2) otitis media caused by Haemophilus influenzae (beta-lactamase positive and negative strains), Moraxella catarrhalis (most of which are beta-lactamase positive), and S. pyogenes, (3) pharyngitis and tonsillitis caused by S. pyogenes, (4) acute bronchitis and acute exacerbations of chronic bronchitis caused by Streptococcus pneumoniae and Haemophilus influenzae (beta-lactamase positive and negative strains), and (5) uncomplicated gonorrhea (cervical/urethral) caused by Neisseria gonorrhoeae (penicillinase- and non-penicillinase-producing strains).

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Cefixime, an antibiotic, is a third-generation cephalosporin like ceftriaxone and cefotaxime. Cefixime is highly stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins due to the presence of beta-lactamases, may be susceptible to cefixime. The antibacterial effect of cefixime results from inhibition of mucopeptide synthesis in the bacterial cell wall.

    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
    CEFIXIME ANHYDROUS
    5.3.2 FDA UNII
    XZ7BG04GJX
    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

    J01DD - Third-generation cephalosporins

    J01DD08 - Cefixime

    5.5 Absorption, Distribution and Excretion

    Absorption

    About 40%-50% absorbed orally whether administered with or without food, however, time to maximal absorption is increased approximately 0.8 hours when administered with food.

    5.6 Metabolism/Metabolites

    Hepatic. Approximately 50% of the absorbed dose is excreted unchanged in the urine in 24 hours.

    5.7 Biological Half-Life

    3-4 hours (may range up to 9 hours). In severe renal impairment (5 to 20 mL/min creatinine clearance), the half-life increased to an average of 11.5 hours.

    5.8 Mechanism of Action

    Like all beta-lactam antibiotics, cefixime binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefixime interferes with an autolysin inhibitor.