cefprozil: structure given in first source
cefprozil : A semisynthetic, second-generation cephalosporin, with prop-1-enyl and (R)-2-amino-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It is used to treat bronchitis as well as ear, skin and other bacterial infections.
ID Source | ID |
---|---|
PubMed CID | 5281006 |
CHEMBL ID | 276568 |
CHEBI ID | 3506 |
SCHEMBL ID | 37024 |
MeSH ID | M0147832 |
Synonym |
---|
cefprozilo |
BIDD:GT0833 |
cefprozilum |
CHEBI:3506 , |
(6r,7r)-7-{[(2r)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-8-oxo-3-(prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
cefzil |
procef |
D07651 |
cefprozil (inn) |
cefprozil (tn) |
C06888 |
cefprozil |
cefprozil anhydrous |
DB01150 |
cefzil (tn) |
cefprozilum [inn-latin] |
cronocef |
serozil |
cefprozilo [inn-spanish] |
bmy 28100 |
arzimol |
5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2r)-amino(4-hydroxyphenyl)acetyl)amino)-8-oxo-3-(1-propenyl)-, (6r,7r)- |
5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((amino(4-hydroxyphenyl)acetyl)amino)-8-oxo-3-(1-propenyl)-, (6r-(6alpha,7beta(r*)))- |
CHEMBL276568 |
C16732 |
s1sdi2fjiy , |
e-cefprozil |
unii-s1sdi2fjiy |
92676-86-3 |
cefprozil anhydrous, e-isomer |
1m698f4h4e , |
cefprozil [usan:inn] |
unii-1m698f4h4e |
AKOS015895989 |
cefprozil e-form [mi] |
5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2r)-amino(4-hydroxyphenyl)acetyl)amino)-8-oxo-3-(1e)-1-propenyl-,(6r,7r)- |
cefprozil anhydrous, (e)- |
cefprozil [mart.] |
bbs-1067 |
bmy-28167 |
(6r,7r)-7-((r)-2-amino-2-(p-hydroxyphenyl)acetamido)-8-oxo-3-propenyl-5-thia-1-azabicyclo(4.2.0)oct-2(e)-ene-2-carboxylic acid |
CCG-221280 |
SCHEMBL37024 |
AB01274812-01 |
trans-cefprozil |
AB01274812_02 |
(6r,7r)-7-[(2r)-2-amino-2-(4-hydroxyphenyl)acetamido]-8-oxo-3-(prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
HMS3715P22 |
(6r,7r)-7-((r)-2-amino-2-(4-hydroxyphenyl)acetamido)-8-oxo-3-((e)-prop-1-enyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
DTXSID10873545 |
Q3231623 |
(e)-cefprozil |
cefprozil hydrate (cefzil) |
WDLWHQDACQUCJR-ZAMMOSSLSA-N |
AS-14301 |
cefprozil, mix of z (92%), and e (7%) isomers |
n,n-bisbenzylidenebenzidine |
(6r,7r)-7-((r)-2-amino-2-(4-hydroxyphenyl)acetamido)-8-oxo-3-((e)-prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
(6r,7r)-7-((r)-2-amino-2-(4-hydroxyphenyl)acetamido)-8-oxo-3-((e)-prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid |
cefprozil (e)-isomer (50 mg)g0d341872ug/mg(ai) |
discontinued. please see c243933. |
cefprozil for peak identification |
EN300-19766374 |
?cefprozil hydrate |
CS-0013517 |
HY-B0458A |
Excerpt | Reference | Relevance |
---|---|---|
"The absolute bioavailability (F) and dose proportionality of cefprozil were investigated in a parallel design study with an embedded two-way crossover leg." | ( Oral absolute bioavailability and intravenous dose-proportionality of cefprozil in humans. Barbhaiya, RH; Campbell, DA; Pittman, KA; Shah, VR; Shyu, WC; Wilber, RB, 1992) | 0.28 |
"The effect of antacid on the bioavailability of cefprozil was investigated in a two-way crossover study." | ( Effect of antacid on the bioavailability of cefprozil. Barbhaiya, RH; Pittman, KA; Shyu, WC; Wilber, RB, 1992) | 0.28 |
" Bioavailability parameters (area under the concentration-time curve from zero to infinity, maximum concentration of the drug in serum, and urinary recovery) indicated an excellent absorption." | ( Multiple-dose pharmacokinetics of cefprozil and its impact on intestinal flora of volunteers. Borner, K; Koeppe, P; Lode, H; Müller, C; Nord, CE, 1992) | 0.28 |
"The absolute bioavailability of cefprozil, a new oral cephalosporin, in four beagles was evaluated." | ( Absolute bioavailability of cefprozil after oral administration in beagles. Barbhaiya, RH; Pittman, KA; Shyu, WC; Wang, L, 1992) | 0.28 |
" The pharmacokinetic study in human indicated that cefprozil was well absorbed and the cis and trans isomers have similar pharmacokinetics." | ( Simultaneous high-performance liquid chromatographic analysis of cefprozil diastereomers in a pharmacokinetic study. Barbhaiya, RH; Papp, EA; Shah, VR; Shukla, UA; Shyu, WC, 1991) | 0.28 |
" This suggests that BMY-28100 is absorbed at a high absorption rate from the gastro-intestinal tract." | ( [Studies on the pharmacokinetics of BMY-28100 (I)]. Esumi, Y; Gunji, S; Ishikawa, H; Ishikawa, K; Jin, Y; Nakanomyo, H; Sonobe, J; Takaichi, M, 1990) | 0.28 |
" However, the absorption rate of cefaclor is significantly reduced in the presence of food, while that of cefprozil remains unaltered." | ( Comparison of the effects of food on the pharmacokinetics of cefprozil and cefaclor. Barbhaiya, RH; Gleason, CR; Pittman, KA; Shukla, UA; Shyu, WC, 1990) | 0.28 |
" This method was sensitive with excellent selectivity and reproducibility, and successfully applied to a bioavailability study of cefprozil in healthy subjects." | ( HPLC method for simultaneous determination of cefprozil diastereomers in human plasma. Jee, JP; Kim, CK; Kim, JK; Park, JS; Park, TH, 2004) | 0.32 |
Excerpt | Relevance | Reference |
---|---|---|
" Twenty-four healthy male subjects divided into 3 dosing groups received a single 250-, 500-, or 1000-mg dose of cefprozil by a 30-minute intravenous infusion." | ( Oral absolute bioavailability and intravenous dose-proportionality of cefprozil in humans. Barbhaiya, RH; Campbell, DA; Pittman, KA; Shah, VR; Shyu, WC; Wilber, RB, 1992) | 0.28 |
" Because of its efficacy and once-daily dosing regimen, cefprozil may be an alternative to currently available oral antibiotics in the treatment of UTIs." | ( Cefprozil versus cefaclor in the treatment of acute and uncomplicated urinary tract infections. Cefprozil Multicenter Study Group. Doyle, CA; Durham, SJ; Iravani, A; Wilber, RB, ) | 0.13 |
" Because renal impairment, but not hepatic dysfunction, significantly reduces the elimination of cefprozil, it is recommended that the dosage be reduced by 50% in patients whose creatinine clearance is less than 30 mL/min." | ( Pharmacology and pharmacokinetics of cefprozil. Barriere, SL, 1992) | 0.28 |
", increased resistance to penicillin and erythromycin and inconvenient dosing schedules) have led to an adjustment in the kinds of antimicrobial agents prescribed for these diseases." | ( Clinical trials of cefprozil for treatment of skin and skin-structure infections: review. Nolen, TM, 1992) | 0.28 |
" Cefprozil was used in single-daily or twice-daily dosing regimens for treatment of infections of the upper and lower respiratory tracts, sinuses, middle ear, urinary tract, and skin and skin structure." | ( Safety profile of cefprozil. Conetta, BJ; DeGraw, SS; Doyle, CA; Durham, SJ; Leigh, A; Wilber, RB, 1992) | 0.28 |
" Based on the efficacy results from this study, the lower gastrointestinal side effects and the convenience of twice-a-day dosing, we believe that cefprozil in a dosage of 30 mg/kg/day divided every 12 hours represents a potential alternative for the treatment of acute otitis media with effusion in children." | ( Comparative trial of cefprozil vs. amoxicillin clavulanate potassium in the treatment of children with acute otitis media with effusion. Arguedas, AG; Blumer, JL; Hains, CS; Stutman, HR; Zaleska, M, 1991) | 0.28 |
" A reduction in dosage is recommended in patients with a creatinine clearance of 30 mL/min or less." | ( Pharmacokinetics of cefprozil in healthy subjects and patients with renal impairment. Barbhaiya, RH; Matzke, GR; Pittman, KA; Shyu, WC; Wilber, RB, 1991) | 0.28 |
" In dogs, watery-mucous diarrhea observed at 2 to 3 hours after dosing in all dose groups was not dose-related." | ( [Single dose oral toxicity study of BMY-28100 in juvenile rats and dogs]. Chikazawa, H; Ishikawa, K; Kadota, T; Kai, S; Kawano, S; Kohmura, H; Kondoh, H; Kuroyanagi, K; Ohta, S; Takahashi, N, 1990) | 0.28 |
" Slightly depressed body weight gains were noted in the 750 and 1,500 mg/kg dose groups during early dosing period." | ( [Four-week repeated dose oral toxicity study of BMY-28100 in juvenile rats]. Chikazawa, H; Ishikawa, K; Kadota, T; Kai, S; Kawano, S; Kohmura, H; Kondoh, H; Kuroyanagi, K; Ohta, S; Takahashi, N, 1990) | 0.28 |
" Fetal tissue concentration of the drug reached a maximum at 6 hours after dosing on day 18 of gestation." | ( [Studies on the pharmacokinetics of BMY-28100 (II)]. Esumi, Y; Gunji, S; Ishikawa, H; Ishikawa, K; Jin, Y; Nakanomyo, H; Sonobe, J; Takaichi, M, 1990) | 0.28 |
" These data suggest that infections caused by highly susceptible pathogens might respond to a twice daily dosing regimen and less susceptible pathogens might require a higher dose or more frequent administration." | ( Pharmacokinetics and tissue penetration of cefprozil. Andrews, JM; Nye, K; O'Neill, P; Wise, R, 1990) | 0.28 |
" If the therapeutic concept is maintained that levels of beta-lactam antibiotics in plasma should exceed the MIC for the offending organisms over a period that approximates the dosing interval, then cefprozil would appear to be suitable for twice-daily administration, whereas cefaclor should probably be administered three or even four times a day." | ( Phase I study of multiple-dose cefprozil and comparison with cefaclor. Barbhaiya, RH; Gleason, CR; Martin, RR; Pittman, KA; Shukla, UA; Shyu, WC; Wilber, RB, 1990) | 0.28 |
" In comparative trials, the clinical and bacteriological efficacy of cefprozil 500mg or 20 mg/kg administered once or twice daily has been comparable with multiple daily dosage regimens of erythromycin in patients with tonsillitis or pharyngitis, with cefaclor and amoxicillin/clavulanate in lower respiratory tract infections, with amoxicillin/clavulanate and erythromycin in skin and skin-structure infections and with cefaclor in acute uncomplicated urinary tract infections." | ( Cefprozil. A review of its antibacterial activity, pharmacokinetic properties, and therapeutic potential. Benfield, P; Wiseman, LR, 1993) | 0.29 |
" In two trials, 891 pediatric patients were enrolled to either cefprozil or amoxicillin-clavulanate dosage regimens." | ( Multi-investigator evaluation of the efficacy and safety of cefprozil, amoxicillin-clavulanate, cefixime and cefaclor in the treatment of acute otitis media. Kafetzis, DA, 1994) | 0.29 |
" Cefprozil demonstrates clinical advantages over many other orally administered beta-lactam antibiotics in terms of antimicrobial spectrum, a once- or twice-daily dosing regimen, and/or reduced incidence of adverse effects." | ( Review of in vitro activity, pharmacokinetic characteristics, safety, and clinical efficacy of cefprozil, a new oral cephalosporin. Barriere, SL, 1993) | 0.29 |
"17 h after dosing are much higher than the MICs for common pathogens which cause pharyngitis or tonsillitis." | ( Penetration of cefprozil into tonsillar and adenoidal tissues. Barbhaiya, RH; Campbell, DA; Reilly, J; Shyu, WC; Wilber, RB, 1993) | 0.29 |
" Simulated pediatric dosage regimens and target peak concentrations in the central compartment were as follows: penicillin V-potassium, 26 mg/kg of body weight every 6 h (q6h) and 14 micrograms/ml; cefaclor, 13." | ( Bactericidal activities of cefprozil, penicillin, cefaclor, cefixime, and loracarbef against penicillin-susceptible and -resistant Streptococcus pneumoniae in an in vitro pharmacodynamic infection model. Cappelletty, DM; Rybak, MJ, 1996) | 0.29 |
" The once-daily dosing schedule for ceftibuten therapy may aid patient compliance, particularly in the pediatric population." | ( Comparison of the efficacy and tolerability of once-daily ceftibuten and twice-daily cefprozil in the treatment of children with acute otitis media. Blumer, JL; Forti, WP; Summerhouse, TL, ) | 0.13 |
" pneumoniae for >40% of the dosing interval." | ( Cefprozil versus high-dose amoxicillin/clavulanate in children with acute otitis media. Hedrick, JA; Pierce, P; Schwartz, RH; Sher, LD, 2001) | 0.31 |
"Current dosing recommendations for cephalosporin antibiotics are on the basis of pharmacokinetic studies and are frequently ignored in practice." | ( Clinical Outcomes of Failing to Dose-Reduce Cephalosporin Antibiotics in Older Adults with CKD. Bathini, L; Battistella, M; Garg, AX; Jain, AK; Jandoc, R; Kuwornu, P; Liu, A; McArthur, E; Muanda, FT; Sood, MM; Weir, MA, 2019) | 0.51 |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID22534 | Half life was measured. | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID198313 | Minimum inhibitory concentration (MIC) against Streptococcus pyogenes by 2-fold microdilution technique | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID117679 | Protective dose (PD50) against Escherichia coli infected mice | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID64069 | Minimum inhibitory concentration (MIC) against Escherichia coli by 2-fold microdilution technique. | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID14190 | Percentage of dose recovered after 0-6 hr in the urine of mice was measured. | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID198183 | Minimum inhibitory concentration (MIC) against Streptococcus pneumoniae by 2-fold microdilution technique | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID79398 | Minimum inhibitory concentration (MIC) against Haemophilus influenzae by 2-fold microdilution technique. | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID200262 | Minimum inhibitory concentration (MIC) against Staphylococcus aureus by 2-fold microdilution technique. | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID198019 | Minimum inhibitory concentration (MIC) against Streptococcus faecalis by 2-fold microdilution technique. | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID64070 | Minimum inhibitory concentration (MIC) was determined as oral therapeutic efficacy against Escherichia coli. | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID117680 | Protective dose (PD50) against Streptococcus pneumoniae infected mice | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID10693 | Area under curve(AUC) was measured in mice after oral administration. | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID64075 | Protective dose (PD50) against Escherichia coli. infected mice; NT means not tested | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID13668 | Cmax was measured in mice after an oral dose of 50 mg/kg. | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID151367 | Minimum inhibitory concentration (MIC) against Proteus mirabilis by 2-fold microdilution technique. | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID94130 | Minimum inhibitory concentration (MIC) against Klebsiella pneumoniae by 2-fold microdilution technique. | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
AID198184 | Minimum inhibitory concentration (MIC) was determined as oral therapeutic efficacy against Streptococcus pneumoniae. | 1988 | Journal of medicinal chemistry, Jun, Volume: 31, Issue:6 | An examination of O-2-isocephems as orally absorbable antibiotics. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 16 (8.99) | 18.7374 |
1990's | 108 (60.67) | 18.2507 |
2000's | 37 (20.79) | 29.6817 |
2010's | 13 (7.30) | 24.3611 |
2020's | 4 (2.25) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.
| This Compound (82.28) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 68 (35.60%) | 5.53% |
Reviews | 24 (12.57%) | 6.00% |
Case Studies | 8 (4.19%) | 4.05% |
Observational | 1 (0.52%) | 0.25% |
Other | 90 (47.12%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |