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MedKoo Cat#: 584352 | Name: Ceftibuten

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ceftibuten is a third-generation cephalosporin antibiotic used primarily for treating bacterial infections, particularly respiratory tract infections. Ceftibuten inhibits bacterial cell wall synthesis by binding to penicillin-binding proteins (PBPs), which are essential enzymes involved in the final steps of peptidoglycan cross-linking. This leads to cell wall weakening and ultimately bacterial cell lysis. ceftibuten is bactericidal and primarily effective against Gram-negative bacteria. Bioactivity: Spectrum of Activity: Ceftibuten is particularly active against Gram-negative organisms, including Haemophilus influenzae, Moraxella catarrhalis, and Escherichia coli. It also has some activity against Gram-positive bacteria but is less effective than earlier-generation cephalosporins. β-lactamase Stability: It is resistant to hydrolysis by many β-lactamases, making it more effective against β-lactamase-producing bacteria. Oral Bioavailability: Ceftibuten is notable for its high oral bioavailability (~90%), making it effective as an oral antibiotic. Pharmacokinetics: It has a long half-life (~4-5 hours), allowing for once-daily dosing.

Chemical Structure

Ceftibuten
CAS#97519-39-6 (free)

Theoretical Analysis

MedKoo Cat#: 584352

Name: Ceftibuten

CAS#: 97519-39-6 (free)

Chemical Formula: C15H14N4O6S2

Exact Mass: 410.0355

Molecular Weight: 410.42

Elemental Analysis: C, 43.90; H, 3.44; N, 13.65; O, 23.39; S, 15.62

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Related CAS #
97519-39-6 (free) 118081-34-8 (hydrate)
Synonym
Ceftibuten; Antibiotic 7432S; Cedax; S 7432
IUPAC/Chemical Name
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)))-
InChi Key
UNJFKXSSGBWRBZ-BJCIPQKHSA-N
InChi Code
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
SMILES Code
O=C(C(N12)=CCS[C@]2([H])[C@H](NC(/C(C3=CSC(N)=N3)=C\CC(O)=O)=O)C1=O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 410.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Demirel I, Kruse R, Önnberg A, Persson K. Ceftibuten-induced filamentation of extended spectrum beta lactamase (ESBL)-producing uropathogenic Escherichia coli alters host cell responses during an in vitro infection. Microb Pathog. 2015 Jan;78:52-62. doi: 10.1016/j.micpath.2014.11.015. Epub 2014 Nov 27. PubMed PMID: 25433242. 2: Jones RN. Ceftibuten: a review of antimicrobial activity, spectrum and other microbiologic features. Pediatr Infect Dis J. 1995 Jul;14(7 Suppl):S77-83. Review. PubMed PMID: 7567314. 3: Mårild S, Jodal U, Sandberg T. Ceftibuten versus trimethoprim-sulfamethoxazole for oral treatment of febrile urinary tract infection in children. Pediatr Nephrol. 2009 Mar;24(3):521-6. doi: 10.1007/s00467-008-0996-6. Epub 2008 Sep 26. PubMed PMID: 18818954. 4: Vilaichone A, Watana D, Chaiwatanarat T. Oral ceftibuten switch therapy for acute pyelonephritis in children. J Med Assoc Thai. 2001 Jun;84 Suppl 1:S61-7. PubMed PMID: 11529382. 5: Sterkers O. Efficacy and tolerability of ceftibuten versus amoxicillin/clavulanate in the treatment of acute sinusitis. Chemotherapy. 1997 Sep-Oct;43(5):352-7. PubMed PMID: 9309369. 6: McCabe R, Rumans L, Perrotta R, Mogabgab W. Comparison of the efficacy and safety of ceftibuten and cefaclor in the treatment of pneumonia and bronchiectasis. J Chemother. 1993 Apr;5(2):124-32. PubMed PMID: 8515295. 7: Krumpe P, Lin CC, Radwanski E, Cayen MN, Affrime MB. The penetration of ceftibuten into the respiratory tract. Chest. 1999 Aug;116(2):369-74. PubMed PMID: 10453864. 8: Orozco H, Sifuentes-Osornio J, Chan C, Medina-Franco H, Vargas-Vorackova F, Prado E, Arch J. Comparison of ceftibuten vs. amoxicillin/clavulanic acid as antibiotic prophylaxis in cholecystectomy and/or biliary tract surgery. J Gastrointest Surg. 2000 Nov-Dec;4(6):606-10. PubMed PMID: 11307095. 9: Aubier MA. Comparison of ceftibuten versus amoxicillin/clavulanate in the treatment of acute exacerbations of chronic bronchitis. Chemotherapy. 1997 Jul-Aug;43(4):297-302. PubMed PMID: 9209787. 10: Koga K, Murakami M, Kawashima S. Modification of ceftibuten transport by changes in lipid fluidity caused by fatty acid glycerol esters. Biol Pharm Bull. 1999 Jan;22(1):103-6. PubMed PMID: 9989674. 11: Debbia EA, Pesce A, Chiesa M, Ricotta N, Schito GC. Microbiologic profile of ceftibuten, a new oral cephalosporin. Drugs Exp Clin Res. 1992;18(4):129-39. PubMed PMID: 1451643. 12: Ho MW, Wang FD, Fung CP, Liu CY. Comparative study of ceftibuten and cefixime in the treatment of complicated urinary tract infections. J Microbiol Immunol Infect. 2001 Sep;34(3):185-9. PubMed PMID: 11605809. 13: Wise R, Andrews JM, Ashby JP, Thornber D. Ceftibuten: a new orally absorbed cephalosporin. In vitro activity against strains from the United Kingdom. Diagn Microbiol Infect Dis. 1991 Jan-Feb;14(1):45-52. PubMed PMID: 2013210. 14: Kardas P, Ratajczyk-Pakalska E. [Patient adherence in respiratory tract infections: ceftibuten versus other antibiotics (PARTICULAR study)]. Pol Merkur Lekarski. 2001 Jun;10(60):445-9. Polish. PubMed PMID: 11503260. 15: Muranushi N, Yoshikawa T, Yoshida M, Oguma T, Hirano K, Yamada H. Transport characteristics of ceftibuten, a new oral cephem, in rat intestinal brush-border membrane vesicles: relationship to oligopeptide and amino beta-lactam transport. Pharm Res. 1989 Apr;6(4):308-12. PubMed PMID: 2748518. 16: Jones RN, Barry AL. Ceftibuten (7432-S, SCH 39720): comparative antimicrobial activity against 4735 clinical isolates, beta-lactamase stability and broth microdilution quality control guidelines. Eur J Clin Microbiol Infect Dis. 1988 Dec;7(6):802-7. PubMed PMID: 3145869. 17: Brismar B, Edlund C, Nord CE. Effect of ceftibuten on the normal intestinal microflora. Infection. 1993 Nov-Dec;21(6):373-5. PubMed PMID: 8132366. 18: Perilli M, Segatore B, Franceschini N, Gizzi G, Mancinelli A, Caravelli B, Setacci D, del Tavio-Perez MM, Bianchi B, Amicosante G. Ceftibuten stability to active-site serine and metallo-beta-lactamases. Int J Antimicrob Agents. 2001 Jan;17(1):45-50. PubMed PMID: 11137648. 19: Lin C, Kumari P, Perrotta RJ, Reidenberg BE. Penetration of ceftibuten into middle ear fluid. Antimicrob Agents Chemother. 1996 Jun;40(6):1394-6. PubMed PMID: 8726007; PubMed Central PMCID: PMC163337. 20: Maraki S, Barbounakis E, Chatzinikolaou I, Anatoliotakis N, Plataki M, Tselentis Y, Samonis G. Effects of cefepime, cefixime and ceftibuten on murine gut colonization by Candida albicans. Chemotherapy. 1998 Nov-Dec;44(6):405-8. PubMed PMID: 9755300.