Page last updated: 2024-11-11

cefetamet

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

cefetamet: active against Neisseria gonorrhoeae; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cefetamet : A cephalosporin compound having methyl and [(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side-groups; a cephalosporin antibiotic active against Neisseria gonorrhoeae. [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]

Cross-References

ID SourceID
PubMed CID5487888
CHEMBL ID2103764
CHEBI ID135629
SCHEMBL ID65620
MeSH IDM0136998

Synonyms (44)

Synonym
cefetamet (usan/inn)
D03424
cemt
65052-63-3
cefetamet [usan:inn]
cefetamet
ly097964
(6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7(sup 2)-(z)-(o-methyloxime)
cefetametum [latin]
3-methyl-7beta-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3,4-didehydrocepham-4-carboxylic acid
cefetametum
CHEBI:135629
deacetoxycefotaxime
(6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(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-carboxylic acid
cefetamet acid;cefetamet;deacetoxycefotaxime
cefetamet hydrochloride
unii-4r5tv783x3
4r5tv783x3 ,
AKOS015898798
cefetamet [usp-rs]
cefetamet [mi]
cefetamet [inn]
(6r,7r)-7-(((2z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetyl)amino)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
cefetamet [mart.]
cefotaxime impurity a [ep impurity]
cefetamet [usan]
cefetamet [usp impurity]
cefotaxime sodium impurity a [ep impurity]
cefetamet [who-dd]
ro 15-8074
ly-097964
ro-15-8074
CHEMBL2103764
ly-97964
SCHEMBL65620
deacetoxycefotaxime, 97%
mfcd00864836
(6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)ethanoyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, aldrichcpr
DTXSID00867110
DB13504
AS-33463
CS-0014040
HY-A0111

Research Excerpts

Overview

Cefetamet pivoxil is an oral cephalosporin with enhanced affinity for the target penicillin-binding proteins 1 and 3. It also has an increased stability to beta-lactamases compared with older cep Halosporins.

ExcerptReferenceRelevance
"Cefetamet is a potent antibiotic to treat respiratory and urinary tract infections. "( Quantitative determination of cefetamet in human plasma by liquid chromatography-mass spectrometry.
Kang, W; Kim, E; Noh, K, 2011
)
2.1
"Cefetamet pivoxil is an oral cephalosporin with enhanced affinity for the target penicillin-binding proteins 1 and 3 and an increased stability to beta-lactamases compared with older cephalosporins, such as cefalexin or cefaclor. "( Pharmacokinetics of cefetamet in plasma and skin blister fluid.
Sansano, S; Wittke, B; Zimmerli, W, 1996
)
2.06
"Cefetamet pivoxil is a new beta lactamase orally stable administered cephalosporin. "( [In vitro activity of cefetamet compared with other antimicrobial agents against bacteria isolated from respiratory tract infections].
Mendes, CM,
)
1.89

Toxicity

ExcerptReferenceRelevance
" Clinical adverse reactions occurred in 22."( [Phase I clinical trial on the safety of injectable cefetamet sodium with a single dose in healthy volunteers].
Li, CZ; Miao, J; Qin, YP; Sun, JY; Wang, Y, 2014
)
0.65

Pharmacokinetics

The pharmacokinetic (PK) and pharmacodynamic (PD) properties of intravenously (IV) administered cefetamet-Na were investigated in eighteen healthy dogs. The mean (+/- standard deviation) half-life of cefatamet was 1.

ExcerptReferenceRelevance
"Differences in the pharmacokinetic parameters of cephalosporins between children and adults may be predictable on the basis of the level of maturation of the physiologic processes involved in drug disposition."( The pharmacokinetics of new oral cephalosporins in children.
Edwards, DJ; Stoeckel, K, 1992
)
0.28
" 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
)
0.56
"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
)
0.83
" pharmacokinetic data on 670 drugs representing, to our knowledge, the largest publicly available set of human clinical pharmacokinetic data."( Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
Lombardo, F; Obach, RS; Waters, NJ, 2008
)
0.35
"The pharmacokinetic (PK) and pharmacodynamic (PD) properties of intravenously (IV) administered cefetamet-Na and per os (PO) administered cefetamet pivoxil were investigated in eighteen healthy dogs at three different dose levels."( Pharmacokinetics and pharmacodynamics of oral and intravenous cefetamet in dog.
Chen, ZH; Gou, S; Wang, CM; Wang, W; Zhao, Y; Zhu, XM, 2015
)
0.88

Bioavailability

Age did not appear to alter the deesterification and bioavailability of cefetamet pivoxil. Cirrhosis had no detectable effect on the pharmacokinetics of cecf. In accordance with the in vitro findings, cefatamet pivotoxil showed good activity in experimental infections in the mouse and rat.

ExcerptReferenceRelevance
"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
)
0.74
" Comparable bioavailability is expected in children and adults."( The pharmacokinetics of new oral cephalosporins in children.
Edwards, DJ; Stoeckel, K, 1992
)
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
)
0.8
" 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
)
0.81
" 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
)
0.84
" 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
)
0.79
" 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
)
0.8
"Oral bioavailability (F) is a product of fraction absorbed (Fa), fraction escaping gut-wall elimination (Fg), and fraction escaping hepatic elimination (Fh)."( Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
Chang, G; El-Kattan, A; Miller, HR; Obach, RS; Rotter, C; Steyn, SJ; Troutman, MD; Varma, MV, 2010
)
0.36

Dosage Studied

The objective of the study was to use Monte Carlo simulation to determine the optimal treatment dosing regimen of the cefetamet sodium for injection. The pharmacokinetics (PK) parameters in healthy Chinese volunteers, and antibacterial activity in vitro was also examined.

ExcerptRelevanceReference
" 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
)
0.58
" An efficacy predictor, measured as the ratios of the time that the concentration of the free drug is over the MIC90 (T > MIC90) and the dosing interval (f% T > MIC90) of IV and PO administration were calculated."( Pharmacokinetics and pharmacodynamics of oral and intravenous cefetamet in dog.
Chen, ZH; Gou, S; Wang, CM; Wang, W; Zhao, Y; Zhu, XM, 2015
)
0.66
"The objective of the study was to use Monte Carlo simulation to determine the optimal treatment dosing regimen of the cefetamet sodium for injection by analysing the pharmacokinetics (PK) parameters in healthy Chinese volunteers, and antibacterial activity in vitro was also examined."( Using Monte Carlo simulation to determine optimal dosing regimen for cefetamet sodium for injection.
Li, C; Miao, J; Qin, Y; Sun, J; Wang, Y; Xiao, Y; Yu, R, 2016
)
0.88
"To investigate the safety and maximum tolerable dosage of injectable cefetamet sodium Sixty healthy volunteers were enrolled in this study."( [Phase I clinical trial on the safety of injectable cefetamet sodium with a single dose in healthy volunteers].
Li, CZ; Miao, J; Qin, YP; Sun, JY; Wang, Y, 2014
)
0.89
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
cephalosporinA class of beta-lactam antibiotics differing from the penicillins in having a 6-membered, rather than a 5-membered, side ring. Although cephalosporins are among the most commonly used antibiotics in the treatment of routine infections, and their use is increasing over time, they can cause a range of hypersensitivity reactions, from mild, delayed-onset cutaneous reactions to life-threatening anaphylaxis in patients with immunoglobulin E (IgE)-mediated allergy.
[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]

Bioassays (35)

Assay IDTitleYearJournalArticle
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID540211Fraction unbound in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079941Liver damage due to vascular disease: peliosis hepatitis, hepatic veno-occlusive disease, Budd-Chiari syndrome. Value is number of references indexed. [column 'VASC' in source]
AID444058Volume of distribution at steady state in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID540209Volume of distribution at steady state in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID444051Total clearance in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID444052Hepatic clearance in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID540213Half life in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1079931Moderate liver toxicity, defined via clinical-chemistry results: ALT or AST serum activity 6 times the normal upper limit (N) or alkaline phosphatase serum activity of 1.7 N. Value is number of references indexed. [column 'BIOL' in source]
AID425652Total body clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID1079938Chronic liver disease either proven histopathologically, or through a chonic elevation of serum amino-transferase activity after 6 months. Value is number of references indexed. [column 'CHRON' in source]
AID1079936Choleostatic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is < 2 (see ACUTE). Value is number of references indexed. [column 'CHOLE' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID444056Fraction escaping gut-wall elimination in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID1079933Acute liver toxicity defined via clinical observations and clear clinical-chemistry results: serum ALT or AST activity > 6 N or serum alkaline phosphatases activity > 1.7 N. This category includes cytolytic, choleostatic and mixed liver toxicity. Value is
AID1079935Cytolytic liver toxicity, either proven histopathologically or where the ratio of maximal ALT or AST activity above normal to that of Alkaline Phosphatase is > 5 (see ACUTE). Value is number of references indexed. [column 'CYTOL' in source]
AID444055Fraction absorbed in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID444053Renal clearance in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
AID540210Clearance in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID540212Mean residence time in human after iv administration2008Drug metabolism and disposition: the biological fate of chemicals, Jul, Volume: 36, Issue:7
Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.
AID444054Oral bioavailability in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID425653Renal clearance in human2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
Physicochemical determinants of human renal clearance.
AID444057Fraction escaping hepatic elimination in human2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID444050Fraction unbound in human plasma2010Journal of medicinal chemistry, Feb-11, Volume: 53, Issue:3
Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination.
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (66)

TimeframeStudies, This Drug (%)All Drugs %
pre-199030 (45.45)18.7374
1990's25 (37.88)18.2507
2000's5 (7.58)29.6817
2010's5 (7.58)24.3611
2020's1 (1.52)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 36.96

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index36.96 (24.57)
Research Supply Index4.41 (2.92)
Research Growth Index4.33 (4.65)
Search Engine Demand Index50.91 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (36.96)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials6 (8.00%)5.53%
Reviews2 (2.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other67 (89.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (1)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
A Clinical Trial to Re-confirm the Efficacy and the Safety of Cefetamet Pivoxil Formulation in Sinusitis Patients: Double Blinded, Randomized, Parallel Designed, Multi-center, Active Comparator Study (CASIS Study) [NCT04664803]Phase 4284 participants (Actual)Interventional2015-08-31Terminated
[information is prepared from clinicaltrials.gov, extracted Sep-2024]