Synthesis and biological properties of sodium (5R,6S,8R)-6.ALPHA.-hydroxyethyl-2-carbamoyloxymethyl-2-penem-3-carboxylate (FCE 22101) and its orally absorbed esters FCE 22553 and FCE 22891.

Franceschi, Giovanni; Foglio, Maurizio; Alpegiani, Marco; Battistini, Carlo; Bedeschi, Angelo; Perrone, Ettore; Zarini, Franco; Arcamone, Federico; Bruna, C. Della; Sanfilippo, A.

doi:10.7164/antibiotics.36.938

Cited by 50 publications

(8 citation statements)

References 5 publications

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“…In addition to appearing to be resistant to the P-lactamases of the Bacteroides spp., it is also extremely active against these strains: the 50% MIC of FCE 22101 being about 16-fold (6). Animal studies show that in mice 47% of the ester FCE 22891 and 32% of FCE 22553 are orally absorbed.…”

Section: Resultsmentioning

confidence: 99%

“…FCE 22101 (Fig. 1) is a new penem having the formula sodium (5R, 6S, 8R)-6-hydroxyethyl-2-carbamoyloxymethyl-2-penem-3-carboxylate and differs from Sch 29,482, which has an ethylthio group in the 2 position (6). In this study, we compared FCE 22101 with other 3-lactams against a wide range of recent clinical isolates and also against strains known to be resistant to certain of these agents.…”

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Comparison of in vitro activity of FCE 22101, a new penem, with those of other beta-lactam antibiotics

Wise¹,

Andrews²,

Danks³

1983

Antimicrob Agents Chemother

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In recent years, there has been great interest in exploiting the biochemical modification of ,-lactam compounds. One area which so far has been less than fruitful is the development of penems. Although many, including Sch 29,482, have been synthesized (2,3,7,9), not one has been fully developed. FCE 22101 (Fig. 1) is a new penem having the formula sodium (5R, 6S, 8R)-6-hydroxyethyl-2-carbamoyloxymethyl-2-penem-3-carboxylate and differs from Sch 29,482, which has an ethylthio group in the 2 position (6). In this study, we compared FCE 22101 with other 3-lactams against a wide range of recent clinical isolates and also against strains known to be resistant to certain of these agents. The effect of serum on the activity of the compound was also studied.MATERIALS AND METHODS Strains and antimicrobial agents. Of the 472 strains examined in this study, 449 were recent clinical isolates from this hospital and are listed in Table 1 Methods. The susceptibilities of the strains to the compounds were studied by a routine agar plate dilution method with Iso-Sensitest agar (pH 7.2) (Oxoid Ltd., Basingstoke, England), which was supplemented as follows: 5% whole horse blood to support growth of streptococci (including S. pneumoniae); a Levinthal preparation (5)

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Comparison of in vitro activity of FCE 22101, a new penem, with those of other beta-lactam antibiotics

Wise¹,

Andrews²,

Danks³

1983

Antimicrob Agents Chemother

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“…Since the first announcements) a decade ago, several publications have appeared in the literature2-15) on new and improved synthetic methodologies to construct a variety of novel penems. At least three candidates, Sch 29482 16), Sch 34343 17) and FCE 22101 18), have been advanced to the clinical trials. Here, as part of a continuing program, we wish to report a new series of 2-heterocyclylalkylthiopenems, which are by far one of the most active series of penems synthesized.…”

Section: Sirmentioning

confidence: 99%

A new class of 2-heterocyclylalkylthiopenems.

Girijavallabhan¹,

Ganguly²,

Pinto³

et al. 1986

J. Antibiot.

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“…The penem FCE 22891 (ritipenem acoxil) can be orally administered and is hydrolized in the intestine into its active moiety, FCE 22101 (7). FCE 22101 is active against staphylococci (including some methicillin-resistant Staphylococcus aureus strains), streptococci, anaerobes (including Bacteroides species), and gram-negative aerobic bacteria, particularly the 3-lactamase-producing strains (17,18,24), but it has little or no activity against Pseudomonas aeruginosa (24).…”

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Clinical and bacteriological efficacy and tolerability of FCE 22891 in patients with exacerbations of chronic obstructive pulmonary disease

Puister¹,

Altena²,

Vries-Hospers³

et al. 1994

Antimicrob Agents Chemother

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A 1-lactamase-stable antibiotic, the oral penem FCE 22891 (ritipenem acoxil), was investigated for use in exacerbations of chronic obstructive pulmonary disease (COPD). Thirteen Exacerbations of chronic obstructive pulmonary disease (COPD) are often caused by viral and bacterial infections, which are the most common causes of death in patients with this disease (5). The three major pathogens isolated from sputum specimens from COPD patients during an exacerbation are Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis. In the past decade an increasing resistance to ampicillin due to production of P-lactamase has been recorded for H. influenzae (15 to 30%) (10, 11, 13) andM.catarrhalis (up to 85%) (8,10,22). When the choice of treatment is empiric, especially in seriously ill patients, the agent should be directed against these P-lactamase-producing bacteria (17).The penem FCE 22891 (ritipenem acoxil) can be orally administered and is hydrolized in the intestine into its active moiety, FCE 22101 (7). FCE 22101 is active against staphylococci (including some methicillin-resistant Staphylococcus aureus strains), streptococci, anaerobes (including Bacteroides species), and gram-negative aerobic bacteria, particularly the 3-lactamase-producing strains (17,18,24) antibiotics during the week preceding admission to the hospital, sputum culture yielding Pseudomonas species, allergy or hypersensitivity to 1-lactam antibiotics, severe renal or liver disease, and pregnancy or breast-feeding.All patients were treated according to standardized therapy. Prednisolone (60 mg/24 h, tapering dosage) and theophylline (500 to 800 mg/24 h) was administered intravenously, salbutamol (2,500 ,ug) and ipratropium bromide (500 ,ug) were administered via a nebulizer four times a day, and FCE 22891 (2 tablets of 500 mg three times a day) was given orally with a meal for 10 days. This was the maximum dosage which was tolerated well when given to healthy individuals in multiple administrations. Moreover, pharmacokinetic studies showed an acceptable bioavailability after a single oral administration of 1 g of FCE 22891 (20).Symptoms were assessed before, during (days 4 and 8), and after (day 11) treatment and during follow-up (day 18) by the same investigator (S.P.). The severity of symptoms (dyspnea, cough, rales, signs of bronchial obstruction, and sputum production) was scaled from 0 to 2 (absent, mild, and severe). Sputum samples were examined and given a score of 0 (absent), 1 (mucous), 2 (mucopurulent), or 3 (purulent) (max-

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Synthesis and biological properties of sodium (5R,6S,8R)-6.ALPHA.-hydroxyethyl-2-carbamoyloxymethyl-2-penem-3-carboxylate (FCE 22101) and its orally absorbed esters FCE 22553 and FCE 22891.

Cited by 50 publications

References 5 publications

Comparison of in vitro activity of FCE 22101, a new penem, with those of other beta-lactam antibiotics

Comparison of in vitro activity of FCE 22101, a new penem, with those of other beta-lactam antibiotics

A new class of 2-heterocyclylalkylthiopenems.

Clinical and bacteriological efficacy and tolerability of FCE 22891 in patients with exacerbations of chronic obstructive pulmonary disease

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