Page last updated: 2024-12-07

cefbuperazone

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Description

cefbuperazone: RN given refers to parent cpd(6R-(6alpha,7alpha,7(2R*,3S*)))-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cefbuperazone : A second-generation cephamycin antibiotic having [(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl and {N-[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]-D-threonyl}amino side groups located at positions 3 and 7beta respectively. [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 CID127527
CHEMBL ID1908372
CHEBI ID135856
SCHEMBL ID49833
MeSH IDM0109887

Synonyms (43)

Synonym
bmy-25182
76610-84-9
D03423
cefbuperazone (usan/inn)
cbpz
cefbuperazone
cefbuperazone [usan:inn]
t-1982
bmy 25182
5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((2-(((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)-3-hydroxy-1-oxobutyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6alpha,7alpha,7(2r*,3s*)))-
cefbuperzaone
cefbuperazona [spanish]
cefbuperazonum [latin]
cerbuperazone [french]
(6r,7s)-7-((2r,3s)-2-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-3-hydroxybutyramido)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
cefbuperazonum
cefbuperazona
(7s)-7-({n-[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]-d-threonyl}amino)-7-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-3,4-didehydrocepham-4-carboxylic acid
(6r,7s)-7-({n-[(4-ethyl-2,3-dioxopiperazin-1-yl)carbonyl]-d-threonyl}amino)-7-methoxy-3-{[(1-methyl-1h-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
cerbuperazone
CHEBI:135856
2,4-bis[(diaminomethylidene)amino]-3,5,6-trihydroxycyclohexyl dihydrogen phosphate
(6r,7s)-7-[[(2r,3s)-2-[(4-ethyl-2,3-dioxopiperazine-1-carbonyl)amino]-3-hydroxybutanoyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
t0785j3x40 ,
unii-t0785j3x40
CHEMBL1908372
AKOS015900594
cefbuperazone [mart.]
cefbuperazone [mi]
cefbuperazone [who-dd]
(6r,7s)-7-[(2r,3s)-2-(4-ethyl-2,3-dioxo-1-piperazinecarboxamido)-3-hydroxybutyramido]-7-methoxy-3-[[(1-methyl-1h-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((2-(((4-ethyl-2,3-dioxo-1-piperazinyl)carbonyl)amino)-3-hydroxy-1-oxobutyl)amino)-7-methoxy-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-, (6r-(6.alpha.,7.alpha.,7(2r*,3s*)))-
cefbuperazone [inn]
cefbuperazone [usan]
SCHEMBL49833
AC-8179
(7s)-7-((2r,3s)-2-(4-ethyl-2,3-dioxopiperazine-1-carboxamido)-3-hydroxybutanamido)-7-methoxy-3-((1-methyl-1h-tetrazol-5-ylthio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
BCP16025
Q5057221
DB13638
gtpl12253
NCGC00507774-01
DTXSID701024595

Research Excerpts

Actions

ExcerptReferenceRelevance
"Cefbuperazone did not inhibit Acinetobacter or Pseudomonas species."( The activity of cefbuperazone, a 7 alpha-methoxy 7 beta acyl ureido cephalosporin.
Chin, NX; Labthavikul, P; Neu, HC, 1985
)
1.34

Pharmacokinetics

Study was carried out using an experimental biliary infection model. The method was successfully applied to a pharmacokinetic study of cefbuperazone in healthy Chinese volunteers.

ExcerptReferenceRelevance
"A study was carried out using an experimental biliary infection model to investigate the pharmacokinetic characteristics and therapeutic effect of cefbuperazone in the rabbit."( Experimental studies on the pharmacokinetics and therapeutic effect of cefbuperazone in biliary infection.
Amemiya, K; Asano, T; Kameyama, J; Kaneda, N; Murakami, N; Senda, H; Tsukamoto, M, 1989
)
0.71
" The simulation curve and pharmacokinetic parameters by one-compartment open model were appropriate for CBPZ levels in the pelvic dead space exudate."( [Pharmacokinetic studies of cefbuperazone in the field of gynecology].
Seiga, K; Sugiyama, Y, 1984
)
0.56

Dosage Studied

ExcerptRelevanceReference
" CBPZ was infused by an intravenous drip method at a dosage of 4-8 g daily."( [Efficacy and safety of cefbuperazone in severe infections complicating hematologic diseases Hanshin Infection Study Group].
Horiuchi, A; Kageyama, T; Kawagoe, H; Kitani, T; Masaoka, T; Nagai, K; Ohyabu, H; Shibata, H; Yasunaga, K; Yonezawa, T, 1988
)
0.58
" Dose-response was observed."( [Laboratory and clinical studies of T-1982 (cefbuperazone) in pediatric infectious diseases].
Aso, K; Kuno, K; Miyachi, Y; Nakashima, T; Ogawa, A; Yafuso, M, 1983
)
0.53
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
peptideAmide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another with formal loss of water. The term is usually applied to structures formed from alpha-amino acids, but it includes those derived from any amino carboxylic acid. X = OH, OR, NH2, NHR, etc.
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 (24)

Assay IDTitleYearJournalArticle
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
AID534391Antibacterial activity against Escherichia coli JM109 by microdilution method2008Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11
KHM-1, a novel plasmid-mediated metallo-beta-lactamase from a Citrobacter freundii clinical isolate.
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' 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]
AID534388Antibacterial activity against Escherichia coli JM109 harboring recombinant pKHM-1 by microdilution method2008Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11
KHM-1, a novel plasmid-mediated metallo-beta-lactamase from a Citrobacter freundii clinical isolate.
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' in source]
AID534385Antibacterial activity against Escherichia coli K-12 W1895 by microdilution method2008Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11
KHM-1, a novel plasmid-mediated metallo-beta-lactamase from a Citrobacter freundii clinical isolate.
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
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]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
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
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]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' in source]
AID1079937Severe hepatitis, defined as possibly life-threatening liver failure or through clinical observations. Value is number of references indexed. [column 'MASS' in source]
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]
AID534382Antibacterial activity against Escherichia coli K-12 W1895 transconjugant harboring pCF243 by microdilution method2008Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11
KHM-1, a novel plasmid-mediated metallo-beta-lactamase from a Citrobacter freundii clinical isolate.
AID534379Antibacterial activity against Citrobacter freundii KHM243 clinical isolate by microdilution method2008Antimicrobial agents and chemotherapy, Nov, Volume: 52, Issue:11
KHM-1, a novel plasmid-mediated metallo-beta-lactamase from a Citrobacter freundii clinical isolate.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (91)

TimeframeStudies, This Drug (%)All Drugs %
pre-199082 (90.11)18.7374
1990's7 (7.69)18.2507
2000's1 (1.10)29.6817
2010's1 (1.10)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.21

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

MetricThis Compound (vs All)
Research Demand Index21.21 (24.57)
Research Supply Index4.58 (2.92)
Research Growth Index4.15 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.21)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials5 (5.43%)5.53%
Reviews0 (0.00%)6.00%
Case Studies3 (3.26%)4.05%
Observational0 (0.00%)0.25%
Other84 (91.30%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]