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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

CAS 97519-39-6
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

CAS 97519-39-6

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 Weight 410.4 g/mol
Molecular Formula C15H14N4O6S2
XLogP3-0.3
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count10
Rotatable Bond Count6
Exact Mass410.03547653 g/mol
Monoisotopic Mass410.03547653 g/mol
Topological Polar Surface Area217 Ų
Heavy Atom Count27
Formal Charge0
Complexity755
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

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.


BUILDING BLOCK

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