Carindacillin (Carbenicillin indanyl)
Carindacillin is a prodrug of carbenicillin ,
administered orally, as the sodium salt.
Dosage and Administration
The adult dosage is 0.5 or 1 g orally every 6 hours. The same doses can be used to treat certain urinary tract infections in patients with mild to moderate degrees of renal failure. The drug is unsuitable for patients with severe renal failure (creatinine clearance <14 ml/min) because very low carbenicillin concentrations are attained in the urine . Carindacillin therapy is not recommended for children.
This drug tastes very bitter and,
although the tablets have a special coating, many patients complain of an
unpleasant after-taste and
Carindacillin is acid stable and is well absorbed when administered orally. After absorption, it is rapidly hydrolyzed to carbenicillin plus indanol, probably either in the intestinal mucosa or in the liver . Following an oral dose of 0.5 g of carindacillin to adults, a peak serum level of about 10 mg/ml carbenicillin is reached in 1.0–1.5 hours. Thereafter, the serum level falls and usually reaches zero at 6 hours. Doubling the dose to 1 g raises the peak serum level to only 15–17 mg/ml. Simultaneous administration of probenecid results in higher serum levels, but they are still inadequate for treatment of systemic P. aeruginosa infections. With dosages larger than 1 g 6-hourly, higher serum levels can be obtained, but not in a dose proportional mode. In patients treated with doses greater than 4 g/day, diarrhea is common because a large proportion of the dose is unabsorbed .
In the ﬁrst 3 hours after an oral dose of 1 g of carindacillin, urine carbenicillin concentrations exceed 1000 mg/ml . All the indanol which is formed when carindacillin is hydrolyzed in vivo is eliminated in the urine as glucuronide and sulfate conjugates .
Mechanism of Action
Other pharmacological effects
CAS number: 26605-69-6 EINECS:
Molecular Formula: C26H26N2O6S
Average mass: 494.559387 Da
Monoisotopic mass: 494.151154 Da
Systematic name: (2S,5R,6R)-6-([3-(2,3-dihydro-1H-inden-5-yloxy)-3-oxo-2-phenylpropanoyl]amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Std. InChI: 1S/C26H26N2O6S/c1-26(2)20(24(31)32)28-22(30)19(23(28)35-26)27-21(29)18(15-7-4-3-5-8-15)25(33)34-17-12-11-14-9-6-10-16(14)13-17/h3-5,7-8,11-13,18-20,23H,6,9-10H2,1-2H3,(H,27,29)(H,31,32)/t18?,19-,20+,23-/m1/s1
Solubility: 0.468 mg/L
1. English A.R., Retsema J.A., Ray V.A., Lynch J.E. "Carbenicillin indanyl sodium, an orally active derivative of carbenicillin". Antimicrob. Agents Chemother. 1 (3): 185–91, (1972).
2. Turck M. "The treatment of urinary-tract infections with an oral carbenicillin". J. Infect. Dis. 127 (Suppl): 133, (1973).
3. Leigh D.A., Simmons K. "The treatment of simple and complicated urinary tract infections with carfecillin, a new oral ester of carbenicillin". J. Antimicrob. Chemother. 2: 293, (1976).
4. Hodges G.R., Perkins R.L. "Carbenicillin indanyl sodium oral therapy of urinary tract infections". Arch. Intern. Med. 131: 679, (1973).
5. Michiels H.G.F., Debruyne F.M.J., Moonen W.A. "The treatment of chronic pyelonephritis with carindacillin". Curr. Med. Res. Opin. 5: 394, (1978).
6. Holloway W.J., Taylor W.A. "Long term oral carbenicillin therapy in complicated urinary tract infections". J. Infect. Dis. 127 (Suppl): 143, (1973).
7. Turck M. "The treatment of urinary-tract infections with an oral carbenicillin". J. Infect. Dis. 127 (Suppl): 133, (1973).
8. Cox C.E. "Pharmacology of carbenicillin indanyl sodium in renal insufﬁciency". J. Infect. Dis. 127 (Suppl): 157, (1973).
9. Knirsch A.K., Hobbs D.C., Korst J.J. "Pharmacokinetics, toleration, and safety of indanyl carbenicillin in man". J. Infect. Dis. 127 (Suppl): 105, (1973).
10. Butler K., English A.R., Ray V.A., Timreck A.E. "Carbenicillin: chemistry and mode of action". J. Infect. Dis. 122 (Suppl): 1, (1970).
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