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Prestwick3_000462

Prestwick3_000462

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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

Prestwick3_000462

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 Formula	C₁₆H₁₅N₅O₇S₂
Molecular Weight	453.5 g/mol
XLogP3	-0.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	8
Exact Mass	453.04129018 g/mol
Monoisotopic Mass	453.04129018 g/mol
Topological Polar Surface Area	238 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	861
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.