CGP-9000
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| Category | Antibiotics |
| Catalog number | BBF-02762 |
| CAS | |
| Molecular Weight | 365.40 |
| Molecular Formula | C16H19N3O5S |
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Description
CGP-9000 is a semisynthetic cephalosporin which has a wide antibacterial spectrum. Its antibacterial activity was similar to that of cefalexin in vitro, but the effect of oral administration was 2-7 times stronger than that of cefalexin and cefradine in mice.
Specification
| Synonyms | CGP 9000; BRN 0587499 |
| IUPAC Name | (7R)-7-[(2-amino-2-cyclohexa-1,4-dien-1-ylacetyl)amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Canonical SMILES | COC1=C(N2C(C(C2=O)NC(=O)C(C3=CCC=CC3)N)SC1)C(=O)O |
| InChI | InChI=1S/C16H19N3O5S/c1-24-9-7-25-15-11(14(21)19(15)12(9)16(22)23)18-13(20)10(17)8-5-3-2-4-6-8/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23)/t10?,11-,15?/m1/s1 |
| InChI Key | RDMOROXKXONCAL-LOIXOFCESA-N |
Reference Reading
1. A randomized double-blind investigation of cefroxadine (CGP 9000) versus cephalexin in urinary tract infection
J Hess, P Gammelgaard, B Holst, F Rasmussen, V F Thomsen Infection. 1984 Jul-Aug;12(4):270-3. doi: 10.1007/BF01645959.
A total of 64 out-patients with significant urinary tract infection were randomly allocated to treatment with cefroxadine 250 mg q.i.d. or cephalexin 500 mg q.i.d. for ten days. Urine cultures were performed before allocation to the treatment groups and on Days 0, 1, 3, 7 and 21. Twenty patients discontinued treatment prematurely because of insignificant bacteriuria on Day 0. Both drug regimes--the cefroxadine dose was half that of cephalexin--showed good activity during treatment, and no statistically significant differences were found between the two drugs. At follow-up, several relapses were found in both treatment groups. Adverse drug reactions were only reported by three patients in the cefroxadine group, and by none in the cephalexin group.
2. Elimination of cefroxadine (CGP-9000) from patients undergoing dialysis
M J Nieto, J M Lanao, A Dominguez-Gil, J M Tabernero, J F Macias Eur J Clin Pharmacol. 1983;24(1):109-12. doi: 10.1007/BF00613936.
The pharmacokinetics of cefroxadine was studied in 17 patients with terminal renal impairment, 10 of whom were undergoing 5 h dialysis sessions. The antibiotic was administered as a single oral dose of 500 mg. Cefroxadine followed a single compartment open kinetic model. During the interdialysis period in patients with terminal renal impairment, an average Cmax of 26.59 micrograms/ml and a tmax of 3.65 h were reached, which are greater than in patients with normal renal function. The serum half-life was reduced from 23.55 h in the interdialysis periods to 3.40 h during the dialysis sessions. The average extraction coefficient was 0.249. It is recommended that a 500 mg dose cefroxadine should be administered at the end of each dialysis session if the interdialysis period is 48 h.
3. Pharmacokinetic properties of the cephalosporins
T Bergan Drugs. 1987;34 Suppl 2:89-104. doi: 10.2165/00003495-198700342-00008.
Most cephalosporins can only be administered parenterally. Among agents that are absorbed from the gastrointestinal tract, those with bioavailabilities of 85 to 90% include cefroxadine, cefadroxil, cefsumide, cephalexin, cephradine, cephacetrile, and cefazaflur. Most cephalosporins are eliminated rapidly, with serum half-lives (t1/2s) of 1 to 2 hours. Exceptions are cefonicid with a t1/2 of 4.4 hours, cefpiramide with a t1/2 of 5.0 hours, and cefotetan with a t1/2 of 3.5 hours. The longest half-life is shown by ceftriaxone with a t1/2 of 8.5 hours. Cephalosporins are eliminated mostly by the kidneys, some with a substantial contribution from active tubular secretion, which is blocked by probenecid. The degree of metabolism varies. Only a few cephalosporins have a high biliary elimination. For example, with intravenously administered cefoperazone, about 70% appears in bile. High biliary elimination is also observed with cefmenoxime, ceftriaxone, cefbuperazone, and latamoxef (moxalactam). Because these are not appreciably absorbed from the gastrointestinal tract, the consequence is high intraintestinal concentrations of the drugs and a marked ensuing depression of the normal microflora with simultaneous emergence of resistant bacteria. The untoward ecological impact may even lead to Clostridium difficile-associated enterocolitis.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
