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Technical details about Ceftibuten Dihydrate, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
1. Also known as: 118081-34-8, Ceftibuten (dihydrate), Ceftibuten.2h2o, Isocef, 62f4443rwp, Ceftibuten hydrate
Molecular Formula
C15H18N4O8S2
Molecular Weight
446.5  g/mol
InChI Key
SSWTVBYDDFPFAF-DKOGRLLHSA-N
FDA UNII
62F4443RWP

Ceftibuten Dihydrate is the dihydrate form of ceftibuten, a semisynthetic, beta-lactamase-stable, third-generation cephalosporin with antibacterial activity. Ceftibuten binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.
1 2D Structure

2D Structure

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;dihydrate
2.1.2 InChI
InChI=1S/C15H14N4O6S2.2H2O/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);2*1H2/b6-1-;;/t10-,13-;;/m1../s1
2.1.3 InChI Key
SSWTVBYDDFPFAF-DKOGRLLHSA-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.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.O.O
2.2 Other Identifiers
2.2.1 UNII
62F4443RWP
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 118081-34-8

2. Ceftibuten (dihydrate)

3. Ceftibuten.2h2o

4. Isocef

5. 62f4443rwp

6. Ceftibuten Hydrate

7. Cetb

8. (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;dihydrate

9. (6r,7r)-7-[[(z)-2-(2-amino-1,3-thiazol-4-yl)-5-hydroxy-5-oxopent-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Dihydrate

10. Seftem

11. (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--water (1/2)

12. 7beta-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino}-3,4-didehydrocepham-4-carboxylic Acid--water(1/2)

13. Unii-62f4443rwp

14. Seftem (tn)

15. Cedax (tn)

16. Ceftibuten Hydrate (jp17)

17. Schembl159144

18. Ceftibuten Hydrate [jan]

19. Chebi:34618

20. Hy-b0698a

21. Ceftibuten Dihydrate [mi]

22. Ceftibuten Dihydrate [vandf]

23. Mfcd08141796

24. S3623

25. Ceftibuten Dihydrate [who-dd]

26. Akos025149353

27. Ccg-269195

28. Cs-4518

29. Ceftibuten Dihydrate [orange Book]

30. D02121

31. 081c348

32. A803878

33. Q27116185

34. (+)-(6r,7r)-7-[2-(2-amino-1,3-thiazol-4-yl)-4-carboxy-2-butenamide]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Dihydrate

35. (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 Dihydrate

36. 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-, Dihydrate, (6r-(6.alpha.,7.beta.(z)))-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 446.5 g/mol
Molecular Formula C15H18N4O8S2
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count12
Rotatable Bond Count6
Exact Mass446.05660589 g/mol
Monoisotopic Mass446.05660589 g/mol
Topological Polar Surface Area219 Ų
Heavy Atom Count29
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 Count3
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