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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

Ceftibuten
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 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 Information
1 of 2  
Drug NameCedax
PubMed HealthCeftibuten (By mouth)
Drug ClassesAntibiotic
Drug LabelCEDAX (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 IngredientCeftibuten dihydrate
Dosage FormCapsule; For suspension
RouteOral
Strengtheq 180mg base/5ml; eq 90mg base/5ml; eq 400mg base
Market StatusPrescription
CompanyPernix Therap

2 of 2  
Drug NameCedax
PubMed HealthCeftibuten (By mouth)
Drug ClassesAntibiotic
Drug LabelCEDAX (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 IngredientCeftibuten dihydrate
Dosage FormCapsule; For suspension
RouteOral
Strengtheq 180mg base/5ml; eq 90mg base/5ml; eq 400mg base
Market StatusPrescription
CompanyPernix 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.


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27-Jan-2021
22-Nov-2024
KGS
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ABOUT THIS PAGE

Ceftibuten Manufacturers

A Ceftibuten manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Ceftibuten, including repackagers and relabelers. The FDA regulates Ceftibuten manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Ceftibuten API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Ceftibuten manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Ceftibuten Suppliers

A Ceftibuten supplier is an individual or a company that provides Ceftibuten active pharmaceutical ingredient (API) or Ceftibuten finished formulations upon request. The Ceftibuten suppliers may include Ceftibuten API manufacturers, exporters, distributors and traders.

click here to find a list of Ceftibuten suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Ceftibuten USDMF

A Ceftibuten DMF (Drug Master File) is a document detailing the whole manufacturing process of Ceftibuten active pharmaceutical ingredient (API) in detail. Different forms of Ceftibuten DMFs exist exist since differing nations have different regulations, such as Ceftibuten USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Ceftibuten DMF submitted to regulatory agencies in the US is known as a USDMF. Ceftibuten USDMF includes data on Ceftibuten's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Ceftibuten USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Ceftibuten suppliers with USDMF on PharmaCompass.

Ceftibuten WC

A Ceftibuten written confirmation (Ceftibuten WC) is an official document issued by a regulatory agency to a Ceftibuten manufacturer, verifying that the manufacturing facility of a Ceftibuten active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Ceftibuten APIs or Ceftibuten finished pharmaceutical products to another nation, regulatory agencies frequently require a Ceftibuten WC (written confirmation) as part of the regulatory process.

click here to find a list of Ceftibuten suppliers with Written Confirmation (WC) on PharmaCompass.

Ceftibuten GMP

Ceftibuten Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Ceftibuten GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Ceftibuten GMP manufacturer or Ceftibuten GMP API supplier for your needs.

Ceftibuten CoA

A Ceftibuten CoA (Certificate of Analysis) is a formal document that attests to Ceftibuten's compliance with Ceftibuten specifications and serves as a tool for batch-level quality control.

Ceftibuten CoA mostly includes findings from lab analyses of a specific batch. For each Ceftibuten CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Ceftibuten may be tested according to a variety of international standards, such as European Pharmacopoeia (Ceftibuten EP), Ceftibuten JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Ceftibuten USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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