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Carbenicillin esters

New B lactam compounds with anti-pseudomonas activity Carbenicillin esters Ticarcillin Lilacillin BL-P1654... [Pg.333]

Pro-drugs (e.g. carbenicillin esters, ampicillin esters Fig. 10.2, Table 10.1) are hydrolysed by enzyme action after absorption from the gut mucosa to produce high blood levels of the active antibiotic, carbenicillin and ampicillin, respectively. [Pg.156]

In Older to improve the poor oral absorption of carbenicillin [4697-36-3] a bpophilic rndanyl ester has been formulated, Geocillin [33331-88-3] (5). Prednisolone [30-24-8] a steroid, is derivatized to its C-21 hemisuccinate sodium salt (6) to make it extremely water-soluble (108). [Pg.397]

C,Hj04 2613-89-0) see Carfecillin Carindacillin phenylmalonic acid benzyl ester chloride (Ci Hi ClO 35353-13-0) see Carbenicillin phenylmalonic acid diethyl ester see under diethyl phenylmalonate phenylmcrcuric acetate... [Pg.2433]

Carbenicillin Carbenicillin, [25 -(2a,5a,6j3)]-3,3-dimethyl-7-oxo-6-(2-carboxy-2-phenylacetamido)-4-thia-l-azabicyclo[3.2.0]-heptan-2-carboxylic acid (32.1.1.32), is synthesized by direct acylation of 6-APA in the presence of sodium bicarbonate by phenylmalonic acid monobenzyl ester chloride, which forms the benzyl ester of carbenicillin (32.1.1.31), the hydrogenolysis of which using palladium on carbon or calcium carbonate as catalyst gives the desired product (32.1.1.32) [51-58]. [Pg.440]

Tablets, film-coated 382 mg carbenicillin (118 mg indanyl sodium ester) Rx)... Tablets, film-coated 382 mg carbenicillin (118 mg indanyl sodium ester) Rx)...
Clocapramine Mnsapramine Pipampernne Piritramide carbenicillin benzyl ester (C24H24N2OfiS 3973-06-6) see Carbenicillin 3-carhethoxyamino-10,11 -dihy dro-5/7-dibenz(6/]azepine (C 7HibNj02 78816-40-7) see Tiracizine JV-carbethoxyphthalimidc... [Pg.2321]

Unlike the situation with ampicillin, the introduetion of asymmetry at the a-ben/.yl carbon in carbenicillin imparts little or no stereoselectivity of antibacterial action the individual enantiomers are nearly equally active and readily epi-nierixcd to the racemate in aqueous solution. Because it is a derivative of phenylmalonic acid, carbcnicillin readily de-carboxylatcs to bcn/.ylpenicillin in the presence of acid therefore, it is not active (as carbcnicillin) orally and must be administered parenterally. Esterification of the compound from acid-cataly/ed destruction and provides an orally active derivative that is hydrolyzed to carbenicillin in the plasma. The plasma levels of free carbenicillin achieved with oral administration of such esters, however, may not suffice fur effective treatment of serious infections caused by some species of Gram-negative bacilli, such as P. aerttgi-no.sa. [Pg.308]

Carbenicillin Indanyl Sodium, USP. Efforts to obtain orally active forms of carbcnicillin led to the eventual rclea.se of the S-indanyl ester carbenicillin indanyl. 6- 2-phcnyl- 2-(S-indanyloxycarbonyl)acctamidolpenicillanic acid (Geocil-lin). in 1972. Approximately 40 >(- of (he usual oral dose of indanyl carbenicillin is absorbed. After ab.sorption. the ester is hydrolyzed rapidly by plasma and tissue e.stcrases to yield carbcnicillin. Thu.s. although the highly lipophilic and highly protein-bound e.ster has in vitro activity comparable with that of carbenicillin. its activity in vivo is due to carbenicillin. Indanyl carbenicillin thus provides an orally active alternative for (he treatment of carbenicillin-sensiiivo sy.stcmic and urinary tract infections caused by Pseudomonas spp.. indole-positive Proteus. spp.. and seleeted species of Gramnegative bacilli. [Pg.313]

The antimicrobial activity of carbenicillin, its indanyl ester (carbenicillin indanyl), and ticarcillin is extended to include Pseudomonas, Enterobacter, and Proteus spp. These agents are inferior to ampicillin against Gram-positive cocci and Listeria monocytogenes and are less active than piperacillin against Pseudomonas. [Pg.478]

This indanyl ester of carbenicillin is excreted rapidly in the urine its only use is for the management of urinary tract infections caused by Proteus spp. other than P. mirabiUs and by P. aeruginosa. [Pg.739]

Carbenicillin indanylsodium effectively treats experimental mouse infections equally well whether administered orally or subcutaneously. The oral ED50 values of the ester also compare favorably with the values obtained after subcutaneous administration of carbenicillin itself. [Pg.403]

Bran et al., (1971) orally administered 1 g of the ester to six fasting subjects. A mean peak serum level of 10.4 p.g/ml for carbenicillin was obtained after 2 hr (36.1% of the dose was recovered in the urine after 6 hr). Pretreatment with 0.5 g of probenecid (8 and 1 hr preceding oral administration of the ester) resulted in an increase to 23.7 p,g/ml of the mean peak serum level of carbenicillin. Neu and Garvey (1975) reported a mean peak serum level of 24 p.g/ml (76% recovery in the urine) after intramuscular administration of 1 g of carbenicillin. [Pg.403]

A potentially useful route to semi-synthetic penicillins by direct acylation of penicillin G imino-chloride esters (187) proceeds through the intermediate diacyl derivatives (188). Selective removal of the phenylacetyl group and ester deblocking with thiophenolate ion afford penicillins (189). A practical application of this route for the synthesis of carbenicillin [189 R = PhCH(COaH)] has been developed. A route to a-carboxyphenylacetamido-cephalosporins (191), by the reaction of isocyanate (190 R = 4-nitrobenzyl) with the anion of t-butyl phenylacetate, has been described. ... [Pg.490]

Certain a-carboxy-aryl esters of carbenicillin, a penicillin that is poorly absorbed from the gastrointestinal tract, have been shown to be absorbed well by the oral route and then hydrolysed efficiently in the body to liberate free carbenicillin. Analogous aliphatic esters are too resistant to hydrolysis to be useful. [Pg.492]


See other pages where Carbenicillin esters is mentioned: [Pg.341]    [Pg.2321]    [Pg.437]    [Pg.943]    [Pg.443]    [Pg.345]    [Pg.346]    [Pg.346]    [Pg.368]    [Pg.110]    [Pg.128]    [Pg.510]    [Pg.11]    [Pg.279]    [Pg.1607]    [Pg.403]    [Pg.404]   
See also in sourсe #XX -- [ Pg.344 , Pg.345 ]

See also in sourсe #XX -- [ Pg.154 , Pg.155 , Pg.156 ]




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