cefetamet pivoxyl: pivaloyloxymethyl ester of Ro 15-8074; structure given in first source; metabolite of cefetamet [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
| ID Source | ID |
|---|---|
| PubMed CID | 5486182 |
| CHEMBL ID | 4303443 |
| CHEBI ID | 135812 |
| SCHEMBL ID | 74256 |
| MeSH ID | M0137004 |
| Synonym |
|---|
| cefyl |
| globocef |
| ro-15-8075 |
| cefetamet pivoxil |
| NCGC00181788-01 |
| cefetamet pivaloyloxymethyl ester |
| 7-(2 (2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-desacetoxyceph-3-em-4-carboxylic acid pivaloyloxymethyl ester |
| cefetamet pivoxyl |
| 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-methyl-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (6r-(6alpha,7beta(z)))- |
| 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-methyl-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (6r,7r)- |
| CHEBI:135812 |
| dasymclqenwcjg-xukdpadisa- |
| inchi=1/c20h25n5o7s2/c1-9-6-33-16-12(23-14(26)11(24-30-5)10-7-34-19(21)22-10)15(27)25(16)13(9)17(28)31-8-32-18(29)20(2,3)4/h7,12,16h,6,8h2,1-5h3,(h2,21,22)(h,23,26)/b24-11-/t12-,16-/m1/s1 |
| 2,2-dimethylpropanoyloxymethyl (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate |
| 65243-33-6 |
| f6xa85n260 , |
| unii-f6xa85n260 |
| cefetamet pivoxil [who-dd] |
| 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-methyl-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (6r-(6.alpha.,7.beta.(z)))- |
| cefatamet pivoxil [mi] |
| cefatamet pivoxil |
| SCHEMBL74256 |
| DTXSID40110016 |
| CHEMBL4303443 |
| 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-methyl-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (6r,7r)- |
| cefditoren impurity 3, cefetamet pivoxil |
| Excerpt | Reference | Relevance |
|---|---|---|
| " Intravenous and oral pharmacokinetic parameters were obtained by using model-independent techniques." | ( Pharmacokinetics of intravenous cefetamet (Ro 15-8074) and oral cefetamet pivoxil (Ro 15-8075) in young and elderly subjects. Blouin, RA; Kneer, J; Stoeckel, K, 1989) | 0.28 |
| "This report summarizes the results of three pharmacokinetic studies of cefetamet and cefetamet pivoxil conducted in normal adult male volunteers." | ( Pharmacokinetics of cefetamet (Ro 15-8074) and cefetamet pivoxil (Ro 15-8075) after intravenous and oral doses in humans. Brandt, R; Dubach, UC; Koup, JR; Stoeckel, K; Wyss, R, 1988) | 0.27 |
| " The average pharmacokinetic parameters from 152 healthy volunteers were: total body clearance 136 ml/min (8." | ( Cefetamet pivoxil clinical pharmacokinetics. Blouin, RA; Stoeckel, K, 1993) | 0.29 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "Five absorption rate models have been compared for describing cefetamet data in 34 adults after oral administration of cefetamet pivoxil with food alone or in combination with either an antacid or an H2 antagonist." | ( Models for describing absorption rate and estimating extent of bioavailability: application to cefetamet pivoxil. Ambros, RJ; Holford, NH; Stoeckel, K, 1992) | 0.28 |
| " Oral bioavailability parameters (area under the concentration-time curve from 0 to 12 h, area under the concentration-time curve from 0 h to infinity, time to maximum concentration of drug in plasma, and maximum concentration of drug in plasma) were obtained by noncompartmental techniques." | ( Influence of antacid and ranitidine on the pharmacokinetics of oral cefetamet pivoxil. Ambros, RJ; Blouin, RA; Kneer, J; Stoeckel, K, 1990) | 0.28 |
| " Cirrhosis had no detectable effect on the pharmacokinetics of cefetamet and on the bioavailability of cefetamet pivoxil." | ( Pharmacokinetics of intravenous cefetamet and oral cefetamet pivoxil in patients with hepatic cirrhosis. Blouin, RA; Hayton, WL; Kneer, J; Stoeckel, K, 1990) | 0.28 |
| " In accordance with the in vitro findings, cefetamet pivoxil showed good activity in experimental infections in the mouse and rat, suggesting satisfactory bioavailability in these animals after oral administration." | ( In vitro antibacterial properties of cefetamet and in vivo activity of its orally absorbable ester derivative, cefetamet pivoxil. Angehrn, P; Hohl, P; Then, RL, 1989) | 0.28 |
| " Age has no effect on the bioavailability of cefetamet pivoxil." | ( Pharmacokinetics of oral cefetamet pivoxil (Ro 15-8075) and intravenous cefetamet (Ro 15-8074) in humans: a review. Kneer, J; Stoeckel, K; Tam, YK, 1989) | 0.28 |
| " Age did not appear to alter the deesterification and bioavailability of cefetamet pivoxil." | ( Pharmacokinetics of intravenous cefetamet (Ro 15-8074) and oral cefetamet pivoxil (Ro 15-8075) in young and elderly subjects. Blouin, RA; Kneer, J; Stoeckel, K, 1989) | 0.28 |
| " In a second study the absolute bioavailability of single 1,500-mg doses of a tablet formulation of the pivaloyloxymethylester of cefetamet was evaluated under conditions of fasting and after a standard breakfast." | ( Pharmacokinetics of cefetamet (Ro 15-8074) and cefetamet pivoxil (Ro 15-8075) after intravenous and oral doses in humans. Brandt, R; Dubach, UC; Koup, JR; Stoeckel, K; Wyss, R, 1988) | 0.27 |
| "Two studies examining the bioavailability of cefetamet pivoxil in healthy male subjects were conducted." | ( Bioavailability of syrup and tablet formulations of cefetamet pivoxil. Ducharme, MP; Edwards, DJ; McNamara, PJ; Stoeckel, K, 1993) | 0.29 |
| " The absolute bioavailability of cefetamet tablets following oral cefetamet pivoxil administration is enhanced by the presence of food." | ( Cefetamet pivoxil clinical pharmacokinetics. Blouin, RA; Stoeckel, K, 1993) | 0.29 |
| "Betalactams, mainly when orally administered, may lead to intestinal flora modifications related to their spectrum of activity, rate of absorption and degradation." | ( Betalactam therapy and intestinal flora. Cassetta, MI; Conti, S; Dei, R; Fallani, S; Mazzei, T; Novelli, A, 1995) | 0.29 |
| " This was considered attributable to the fact that the bioavailability of carnitine is as low as 16% when administered orally, which is considerably less compared to the 55% bioavailability of cefetamet pivoxil." | ( [Influence of multiple-dose administration of cefetamet pivoxil on blood and urinary concentrations of carnitine and effects of simultaneous administration of carnitine with cefetamet pivoxil]. Ishii, I; Kosuge, K; Nakashima, M; Ohtsubo, M, 1996) | 0.29 |
| " It is concluded that (i) the Delta2 isomerization does not significantly affect the bioavailability of prodrug esters since enzymatic hydrolysis in the intestinal fluid proceeds mainly to the active Delta3-cephalosporin and (ii) the high degree of stereoselectivity of the enzymatic ester hydrolysis should make it possible to increase the bioavailabilities of certain prodrug esters (CAE, CPD) by using the more stable diasterioisomer." | ( Stability of cephalosporin prodrug esters in human intestinal juice: implications for oral bioavailability. Blouin, RA; Duchene, P; Hofheinz, W; Laneury, JP; Shedlofsky, S; Stoeckel, K, 1998) | 0.3 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " Recruitment for this dosage group is being continued." | ( Comparative study of cefetamet pivoxil and penicillin V in the treatment of group A beta-hemolytic streptococcal pharyngitis. De Boeck, K; Pierard, D; Ramet, J; Vandenberghe, P, 1992) | 0.28 |
| " Each subject received, in an open-labeled, randomized, three-way crossover design, a single oral dose of 1,000 mg (two tablets) of cefetamet pivoxil 10 min after a standard breakfast during each of the following treatments: treatment A, control period; treatment B, antacid (80 ml of suspension; Maalox 70) administered on the evening before cefetamet pivoxil dosing (-12." | ( Influence of antacid and ranitidine on the pharmacokinetics of oral cefetamet pivoxil. Ambros, RJ; Blouin, RA; Kneer, J; Stoeckel, K, 1990) | 0.28 |
| " In patients with varying degrees of renal insufficiencies, dosage should be decreased accordingly." | ( Pharmacokinetics of oral cefetamet pivoxil (Ro 15-8075) and intravenous cefetamet (Ro 15-8074) in humans: a review. Kneer, J; Stoeckel, K; Tam, YK, 1989) | 0.28 |
| " In 336 children, 240 received cefetamet pivoxil at 2 dosage levels (10 or 20 mg/kg twice daily) for 7 to 12 days and 96 received the standard comparator, cefaclor (10 mg/kg 3 times daily)." | ( Comparative clinical efficacy of cefetamet pivoxil in lower respiratory tract infection. Grassi, GG, 1994) | 0.29 |
| " Despite the lower bioavailability of the syrup, unbound-cefetamet concentrations are expected to remain above the MICs for 90% of the strains tested for susceptible organisms for approximately 10 h of the usual 12-h dosing interval with both syrup and tablet formulations of cefetamet pivoxil given with food." | ( Bioavailability of syrup and tablet formulations of cefetamet pivoxil. Ducharme, MP; Edwards, DJ; McNamara, PJ; Stoeckel, K, 1993) | 0.29 |
| " Similar absorption characteristics have been observed for all of the tablet dosage formulations studied during clinical development." | ( Cefetamet pivoxil clinical pharmacokinetics. Blouin, RA; Stoeckel, K, 1993) | 0.29 |
| " Cefetamet pivoxil is a new oral cephalosporin with a twice daily dosage and striking stability against beta-lactamases." | ( Cefetamet pivoxil in the treatment of pharyngotonsillitis due to group A beta-hemolytic streptococci: preliminary report. Brighi, L; Gervaix, A; Halpérin, DS; Suter, S, 1995) | 0.29 |
| Class | Description |
|---|---|
| 1,3-thiazoles | |
| oxime O-ether | O-organyl oximes R2C=NOR' (R' =/= H). |
| cephams | Natural and synthetic antibiotics containing the 5-thia-1-azabicyclo[4.2.0]octan-8-one nucleus; generally assumed to have the 6R configuration, unless otherwise specified. |
| pivaloyloxymethyl ester | A acetal obtained from a carboxylic acid by replacement of the hydrogen attached to the carboxy group by a pivaloyloxymethyl group. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 18 (27.69) | 18.7374 |
| 1990's | 40 (61.54) | 18.2507 |
| 2000's | 4 (6.15) | 29.6817 |
| 2010's | 2 (3.08) | 24.3611 |
| 2020's | 1 (1.54) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 32 (45.07%) | 5.53% |
| Reviews | 8 (11.27%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 31 (43.66%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||