Ceftibuten

(BAN, USAN, rINN)
Synonyms: Ceftibutène; Ceftibuteno; Ceftibutenum; Keftibuteeni; 7432-S; Sch-39720. 7-[2-(2-Amino-1,3-thiazol-4-yl)-4-carboxyisocrotonamide]-3-cephem-4carboxylic acid.
Cyrillic synonym: Цефтибутен.

💊 Chemical information

Chemical formula: C15H14N4O6S2 = 410.4.
CAS — 97519-39-6.
ATC — J01DD14.
ATC Vet — QJ01DD14.

Pharmacopoeias.

Jpn includes the dihydrate.

💊 Adverse Effects and Precautions

As for Cefalotin Sodium. The most frequently reported adverse effects of ceftibuten are gastrointestinal disturbances, especially diarrhoea, and headache.

💊 Antimicrobial Action

As for Cefixime. It is less active in vitro against Streptococcus pneumoniae.
1. Shawar R, et al. Comparative in vitro activity of ceftibuten (Sch39720) against bacterial enteropathogens. Antimicrob Agents Chemother 1989; 33: 781–4
2. Bragman SGL, Casewell MW. The in-vitro activity of ceftibuten against 475 clinical isolates of Gram-negative bacilli, compared with cefuroxime and cefadroxil. J Antimicrob Chemother 1990; 25: 221–6
3. Wise R, et al. Ceftibuten—in-vitro activity against respiratory pathogens, β-lactamase stability and mechanism of action. J Antimicrob Chemother 1990; 26: 209–13
4. Maioli E, et al. In vitro activity of ceftibuten at sub-inhibitory concentrations in comparison with other antibiotics against respiratory and urinary tract pathogens. J Chemother 2007; 19: 152–60.

💊 Pharmacokinetics

Ceftibuten is rapidly absorbed from the gastrointestinal tract, although the rate and extent of absorption are somewhat decreased by the presence of food. Peak plasma concentrations of about 17 micrograms/mL are attained about 2 hours after a 400-mg dose. The plasma half-life of ceftibuten is about 2.0 to 2.3 hours and is prolonged in patients with renal impairment. Ceftibuten is 65 to 77% bound to plasma proteins. Ceftibuten distributes into middle-ear fluid and bronchial secretions. About 10% of a dose is converted to the trans-isomer, which has about one-eighth of the activity of the cis-isomer. Ceftibuten is excreted mainly in the urine and also in the faeces. Significant amounts are removed by haemodialysis.

💊 Uses and Administration

Ceftibuten is a third-generation cephalosporin antibacterial used similarly to cefixime in the treatment of urinary-tract and respiratory-tract infections. It is given orally as the dihydrate, but doses are expressed in terms of anhydrous ceftibuten; 435 mg of ceftibuten dihydrate is equivalent to about 400 mg of anhydrous ceftibuten. The usual adult dose is 400 mg once daily on an empty stomach. Children over 6 months of age and weighing 45 kg or less may be given 9 mg/kg daily as a single dose. For reduced doses in patients with moderate to severe renal impairment, see below.
1. Wiseman LR, Balfour JA. Ceftibuten: review of its antibacterial activity, pharmacokinetic properties and clinical efficacy. Drugs 1994; 47: 784–808
2. Nelson JD, McCracken GH (eds). Ceftibuten: a new orally active cephalosporin for pediatric infections. Pediatr Infect Dis J 1995; 14 (suppl): S76–S133
3. Guay DRP. Ceftibuten: a new expanded-spectrum oral cephalosporin. Ann Pharmacother 1997; 31: 1022–33
4. Owens RC, et al. Ceftibuten: an overview. Pharmacotherapy 1997; 17: 707–20.

Administration in renal impairment.

Doses of ceftibuten should be reduced in patients with moderate to severe renal impairment. The following doses based on creatinine clearance (CC) may be used:
CC 30 to 49 mL/minute: 200 mg once daily
CC 5 to 29 mL/minute: 100 mg once daily
Patients undergoing haemodialysis 2 or 3 times weekly may be given a dose of 400 mg after each dialysis session.

💊 Preparations

Proprietary Preparations

Arg.: Cedax†; Sepex†; Austria: Caedax†; Cz.: Cedax†; Ger.: Keimax; Gr.: Caedax†; Hong Kong: Cedax; Hung.: Cedax; India: Procadax; Israel: Cedax; Ital.: Cedax; Isocef; Jpn: Seftem; Malaysia: Cedax; Mex.: Cedax; Neth.: Cedax; Philipp.: Cedax; Pol.: Cedax; Port.: Caedax; Rus.: Cedax (Цедекс); S.Afr.: Cedax†; Sepexin†; Singapore: Cedax; Spain: Biocef; Cedax; Cepifran†; Swed.: Cedax; Switz.: Cedax; Thai.: Cedax; USA: Cedax; Venez.: Cedax; Sepexin†.
Published January 14, 2019.