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Ceftibuten

Synopsis, Chemistry

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Also known as: 97519-39-6, Cedax, Ceftibuteno, Ceftibutenum, Ceftibutene, Sch 39720

Molecular Formula

C₁₅H₁₄N₄O₆S₂

Molecular Weight

410.4 g/mol

InChI Key

UNJFKXSSGBWRBZ-BJCIPQKHSA-N

FDA UNII

IW71N46B4Y

A cephalosporin antibacterial agent that is used in the treatment of infections, including urinary-tract and respiratory-tract infections.

Ceftibuten is a Cephalosporin Antibacterial.

1 2D Structure

Ceftibuten

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6R,7R)-7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

2.1.2 InChI

InChI=1S/C15H14N4O6S2/c16-15-17-7(5-27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-8(14(24)25)3-4-26-13(10)19/h1,3,5,10,13H,2,4H2,(H2,16,17)(H,18,22)(H,20,21)(H,24,25)/b6-1-/t10-,13-/m1/s1

2.1.3 InChI Key

UNJFKXSSGBWRBZ-BJCIPQKHSA-N

2.1.4 Canonical SMILES

C1C=C(N2C(S1)C(C2=O)NC(=O)C(=CCC(=O)O)C3=CSC(=N3)N)C(=O)O

2.1.5 Isomeric SMILES

C1C=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)/C(=C\CC(=O)O)/C3=CSC(=N3)N)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

IW71N46B4Y

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 7-(2-(2-amino-4-thiazolyl)-4-carboxy-2-butenoylamino)-3-cephem-4-carboxylic Acid

2. 7432 S

3. 7432-s

4. Cedax

5. Sch 39720

6. Sch-39720

7. Sch39720

2.3.2 Depositor-Supplied Synonyms

1. 97519-39-6

2. Cedax

3. Ceftibuteno

4. Ceftibutenum

5. Ceftibutene

6. Sch 39720

7. Ceftibuten Hydrate

8. Cis-ceftibuten

9. Sch-39720

10. 7432-s

11. Antibiotic 7432s

12. Nsc-758925

13. Achn383

14. Achn-383

15. Chebi:3510

16. Iw71n46b4y

17. (+)-(6r,7r)-7-((z)-2-(2-amino-4-thiazolyl)-4-carboxycrotonamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

18. Ceftibuten Dihydrate

19. Cis-ceftibutin

20. 97519-39-6 (free)

21. Isocef

22. Cetb

23. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((2-(2-amino-4-thiazolyl)-4-carboxy-1-oxo-2-butenyl)amino)-8-oxo-, (6r-(6alpha,7beta(z)))-

24. Cephalosporin 7432-s

25. (6r,7r)-7-[[(z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

26. (6r,7r)-7-((z)-2-(2-aminothiazol-4-yl)-4-carboxybut-2-enamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

27. Ceftibutene [inn-french]

28. Ceftibutenum [inn-latin]

29. Ceftibuteno [inn-spanish]

30. Unii-iw71n46b4y

31. Ceftibutin

32. Ceprifran

33. Ceftem

34. Keimax

35. Ceftibuten [usan:inn:ban]

36. S 7432

37. Ncgc00095137-01

38. Ceftibuten-13c3

39. Ceftibuten, 95%

40. Mfcd00864918

41. Ceftibuten [mi]

42. Ceftibuten [inn]

43. Ceftibuten (usan/inn)

44. Spectrum5_001558

45. Ceftibuten [usan]

46. Ceftibuten [vandf]

47. Ceftibutin [vandf]

48. Ceftibuten [who-dd]

49. Chembl1605

50. Dsstox_cid_25925

51. Dsstox_rid_81227

52. Dsstox_gsid_45925

53. Schembl37054

54. Bspbio_002733

55. Spectrum1505207

56. Dtxsid4045925

57. Gtpl12029

58. Hms1922l17

59. Hms2093k18

60. Hms3715p10

61. Pharmakon1600-01505207

62. Hy-b0698

63. Zinc3871967

64. Tox21_111446

65. Bdbm50370586

66. Ccg-39440

67. Nsc758925

68. Akos005146205

69. Akos015854930

70. Db01415

71. Nsc 758925

72. Ncgc00178501-01

73. Ncgc00178501-04

74. Sbi-0206740.p001

75. Cas-97519-39-6

76. C-2550

77. C08117

78. D00922

79. Ab01563048_01

80. 519c396

81. Ceftibuten, Antibiotic For Culture Media Use Only

82. Q419521

83. Sr-05000001989

84. Sr-05000001989-1

85. 7-[2-(2-amino-1,3-thiazol-4-yl)-4-carboxyisocrotonamide]-3-cephem-4-carboxylicacid

86. (6r,7r)-7-[(2z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

87. (6r,7r)-7-[[(2z)-2-(2-amino-4-thiazolyl)-4-carboxy-1-oxo-2-buten-1-yl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

88. (6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

89. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((2-(2-amino-4-thiazolyl)-4-carboxy-1-oxo-2-butenyl)amino)-8-oxo-, (6r-(6.alpha.,7.beta.(z)))-

90. 7beta-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino}-3,4-didehydrocepham-4-carboxylic Acid

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₄N₄O₆S₂
Molecular Weight	410.4 g/mol
XLogP3	-0.3
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	6
Exact Mass	410.03547653 g/mol
Monoisotopic Mass	410.03547653 g/mol
Topological Polar Surface Area	217 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	755
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 Information

1 of 2
Drug Name	Cedax
PubMed Health	Ceftibuten (By mouth)
Drug Classes	Antibiotic
Drug Label	CEDAX (ceftibuten capsules) and (ceftibuten for oral suspension) contain the active ingredient ceftibuten as ceftibuten dihydrate. Ceftibuten dihydrate is a semisynthetic cephalosporin antibiotic for oral administration. Chemically, it is (+)-(6R,7R)...
Active Ingredient	Ceftibuten dihydrate
Dosage Form	Capsule; For suspension
Route	Oral
Strength	eq 180mg base/5ml; eq 90mg base/5ml; eq 400mg base
Market Status	Prescription
Company	Pernix Therap

2 of 2
Drug Name	Cedax
PubMed Health	Ceftibuten (By mouth)
Drug Classes	Antibiotic
Drug Label	CEDAX (ceftibuten capsules) and (ceftibuten for oral suspension) contain the active ingredient ceftibuten as ceftibuten dihydrate. Ceftibuten dihydrate is a semisynthetic cephalosporin antibiotic for oral administration. Chemically, it is (+)-(6R,7R)...
Active Ingredient	Ceftibuten dihydrate
Dosage Form	Capsule; For suspension
Route	Oral
Strength	eq 180mg base/5ml; eq 90mg base/5ml; eq 400mg base
Market Status	Prescription
Company	Pernix Therap

4.2 Drug Indication

Indicated for the treatment of acute bacterial exacerbations of chronic bronchitis (ABECB), acute bacterial otitis media, pharyngitis, and tonsilitis.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Ceftibuten is an antibiotic with bactericidal actions.

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

CEFTIBUTEN

5.3.2 FDA UNII

IW71N46B4Y

5.3.3 Pharmacological Classes

Chemical Structure [CS] - Cephalosporins

5.4 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DD - Third-generation cephalosporins

J01DD14 - Ceftibuten

5.5 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed following oral administration.

Route of Elimination

Ceftibuten is excreted in the urine; 95% of the administered radioactivity was recovered either in urine or feces.

Volume of Distribution

0.21 L/kg [adult subjects]

0.5 L/kg [fasting pediatric patients]

5.6 Metabolism/Metabolites

A study with radiolabeled ceftibuten administered to 6 healthy adult male volunteers demonstrated that cis-ceftibuten is the predominant component in both plasma and urine. About 10% of ceftibuten is converted to the trans-isomer is approximately 1/8 as antimicrobially potent as the cis-isomer.

5.7 Mechanism of Action

Ceftibuten exerts its bactericidal action by binding to essential target proteins of the bacterial cell wall. This binding leads to inhibition of cell-wall synthesis.