Page last updated: 2024-12-10

cefroxadine

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

Description

cefroxadine: orally active, broad spectrum cephalosporin [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

cefroxadine : A first-generation cephalosporin antibiotic having methoxy and [(2R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetyl]amino side groups located at positions 3 and 7 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 CID5284529
CHEMBL ID3186538
CHEBI ID31379
SCHEMBL ID147239
MeSH IDM0059907

Synonyms (53)

Synonym
(6r,7r)-7-{[(2r)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetyl]amino}-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
cgp-9000
oraspor
51762-05-1
cefroxadine
cefroxadine (usan)
cefthan-ds (tn)
D01528
cxd ,
antibiotic cgp 9000
cefroxadin
7-(d-2-amino-2-(1,4-cyclohexadienyl)acetamide)-3-methoxy-3-cephem-4-carboxylic acid
cefroxadinum [inn-latin]
brn 0587499
einecs 257-391-8
cefroxadine [usan:inn:jan]
cgp 9000
(6r,7r)-7-((r)-2-amino-2-(1,4-cyclohexadien-1-yl)acetamido)-3-methoxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
cefroxadino [inn-spanish]
5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((amino-1,4-cyclohexadien-1-ylacetyl)amino)-3-methoxy-8-oxo-, (6r-(6alpha,7beta(r*)))-
AC1NR4MM ,
(6r,7r)-7-[[(2r)-2-amino-2-cyclohexa-1,4-dien-1-ylacetyl]amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
dtxcid602768
tox21_113142
dtxsid1022768 ,
cas-51762-05-1
cefroxadino
cefroxadinum
unii-b908c4mv2r
b908c4mv2r ,
cefroxadine [inn]
cefroxadine [who-dd]
5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-((amino-1,4-cyclohexadien-1-ylacetyl)amino)-3-methoxy-8-oxo-, (6r-(6a,7b(r*)))-
cefroxadine [mi]
cefroxadine [mart.]
(6r,7r)-7-[(r)-2-amino-2-(1,4-cyclohexadien-1-yl)acetamido]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
cefroxadine [usan]
cefthan-ds
SCHEMBL147239
7-{[(2r)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetyl]amino}-3-methoxy-3,4-didehydrocepham-4-carboxylic acid
CHEBI:31379 ,
dsstox_cid_2768
(6r,7r)-7-[[(2r)-2-amino-2-cyclohexa-1,4-dien-1-yl-acetyl]amino]-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
surecn147239
dsstox_rid_76723
CHEMBL3186538
DB11367
Q5057294
(6r,7r)-7-((r)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetamido)-3-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
51762-05-1 (free)
CS-0027250
HY-107064
AKOS040744851

Research Excerpts

Overview

Cefroxadine is an orally administered synthesized cephalosporin antibiotic developed by Ciba-Geigy Limited (Switzerland) in 1972.

ExcerptReferenceRelevance
"Cefroxadine (CXD) is an orally administered synthesized cephalosporin antibiotic developed by Ciba-Geigy Limited (Switzerland) in 1972. "( [Clinical use of cefroxadine in dentistry and oral surgery].
Kikuta, T; Kinebuchi, T; Masuda, N; Takarada, H, 1983
)
2.05

Pharmacokinetics

The pharmacokinetic parameters of cefroxadine were obtained by analysing the serum level data of the drug based on a one-compartment open model.

ExcerptReferenceRelevance
" The trauma patients exhibited significantly lower Cmax and reduced AUC."( Peroral absorption of cefroxadine in patients within the first day after severe trauma: comparison to cefroxadine pharmacokinetics in fasted, healthy volunteers.
Aiache, JM; Beyssac, E; Haberer, JP; Ritschel, WA, 1991
)
0.6
" The serum concentrations, serum elimination half-life and total body clearance were significantly influenced by reduced renal function."( Relationship between pharmacokinetics and bioavailability of cefroxadine (CGP 9000) and renal function.
Bergan, T; Brodwall, EK; Larsen, EW, 1983
)
0.51
"A pharmacokinetic model has been developed, by means of which all possible time courses of the concentrations of antibiotics in the plasma of treated individuals can be exactly simulated in vitro without diluting the test organism and affecting the growth curves."( Antibacterial effects of cefroxadine, cephalexin and cephradine in a new in vitro pharmacokinetic model.
Maurer, M; Schneider, P; Tosch, W; Zak, O, 1982
)
0.57
" The pharmacokinetic parameters of cefroxadine were obtained by analysing the serum level data of the drug based on a one-compartment open model."( Pharmacokinetics of cefroxadine in healthy volunteers and patients with impaired renal function.
Awazu, S; Kuroda, K; Ohkawa, M; Shimamura, M; Takamae, K, 1981
)
0.86
"The pharmacokinetic parameters of cefroxadin and cephalexin were compared after simultaneous oral administration of the two cephalosporins to 21 subjects."( Pharmacokinetic comparison of cefroxadin (CGP 9000) and cephalexin by simultaneous administration to humans.
Hirtz, JL; Humbert, G; Lecaillon, JB; Schoeller, JP; Vischer, W, 1980
)
0.26
" This assay was successfully applied to determine the pharmacokinetic parameters of cefroxadine in Korean healthy volunteers after an oral administration of two 250 mg cefroxadine capsules."( A specific and rapid HPLC assay for the determination of cefroxadine in human plasma and its application to pharmacokinetic study in Korean.
Choi, HM; Kang, YS; Kim, NH; Kim, W; Lee, HJ; Lee, SY; Park, JS, 2006
)
0.8

Bioavailability

ExcerptReferenceRelevance
" Even though rate and extent of bioavailability cannot be determined from these two different population groups since the total clearance must be assumed to be different in patients and healthy subjects, a reduced bioavailability is assumed based on pathophysiologic reflections."( Peroral absorption of cefroxadine in patients within the first day after severe trauma: comparison to cefroxadine pharmacokinetics in fasted, healthy volunteers.
Aiache, JM; Beyssac, E; Haberer, JP; Ritschel, WA, 1991
)
0.6
" Both drugs were equally well absorbed from all of the tested formulations; identical percentages of the dose were recovered in the urine in all cases."( Pharmacokinetic comparison of cefroxadin (CGP 9000) and cephalexin by simultaneous administration to humans.
Hirtz, JL; Humbert, G; Lecaillon, JB; Schoeller, JP; Vischer, W, 1980
)
0.26
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" Tonsillar tissues were taken 2 h after dosing and blood samples before, 1, 2, 4 and 6 h after the drug administration in 8 out of 20 enrolled patients."( Correlation between plasma and tonsillar levels of cefroxadine.
Bichisao, E; Borghi, C; Fraschini, F; Montanari, M; Scaglione, F; Vago, F, 1988
)
0.53
" Cefroxadine dry syrup was in principle administered at the dosage of 10 mg per kilogram of body weight 3 times a day."( [Use of cefroxadine dry syrup in the management of acute skin infections in children (author's transl)].
Arakawa, K; Arata, J; Fujimoto, W; Hagiyama, M; Hiramatsu, H; Kashiwa, N; Masuda, T; Miyoshi, K; Nakagawa, S; Nakakita, T; Nishihara, O; Nishimoto, M; Nohara, N; Okuma, N; Suwaki, M; Tada, J; Take, M; Tanaka, A; Tokumaru, S; Ueki, H; Umemura, S; Yamada, M; Yamamoto, Y, 1981
)
1.61
" Clinical responses: CXD was administered, for 7 days, to 33 children with scarlet fever in the dosage of greater than or equal 20 approximately less than 60 mg/kg/day (7 children in greater than or equal to 20 approximately 30 mg/kg/day, 21 in greater than or equal to 30 approximately less than 40 mg/kg/day and 5 in greater than or equal to 40 approximately less than 60 mg/kg/day)."( [Clinical evaluation of cefroxadine dry syrup in pediatric field (author's transl)].
Hachimori, K; Minamikawa, I; Minamitani, M; Suzuki, M, 1981
)
0.57
[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]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
estrogen nuclear receptor alphaHomo sapiens (human)Potency0.53540.000229.305416,493.5996AID743075
Spike glycoproteinSevere acute respiratory syndrome-related coronavirusPotency17.78280.009610.525035.4813AID1479145
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Ceullar Components (1)

Processvia Protein(s)Taxonomy
virion membraneSpike glycoproteinSevere acute respiratory syndrome-related coronavirus
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
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]
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]
AID1079948Times to onset, minimal and maximal, observed in the indexed observations. [column 'DELAI' in source]
AID1079949Proposed mechanism(s) of liver damage. [column 'MEC' 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]
AID1079944Benign tumor, proven histopathologically. Value is number of references indexed. [column 'T.BEN' in source]
AID1079947Comments (NB not yet translated). [column 'COMMENTAIRES' 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
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]
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]
AID1079942Steatosis, proven histopathologically. Value is number of references indexed. [column 'STEAT' in source]
AID1079934Highest frequency of acute liver toxicity observed during clinical trials, expressed as a percentage. [column '% AIGUE' in source]
AID1079939Cirrhosis, proven histopathologically. Value is number of references indexed. [column 'CIRRH' in source]
AID1079945Animal toxicity known. [column 'TOXIC' in source]
AID1079940Granulomatous liver disease, proven histopathologically. Value is number of references indexed. [column 'GRAN' in source]
AID1079932Highest frequency of moderate liver toxicity observed during clinical trials, expressed as a percentage. [column '% BIOL' 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]
AID1079943Malignant tumor, proven histopathologically. Value is number of references indexed. [column 'T.MAL' in source]
AID1079946Presence of at least one case with successful reintroduction. [column 'REINT' in source]
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (72)

TimeframeStudies, This Drug (%)All Drugs %
pre-199059 (81.94)18.7374
1990's8 (11.11)18.2507
2000's1 (1.39)29.6817
2010's2 (2.78)24.3611
2020's2 (2.78)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 31.99

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 Index31.99 (24.57)
Research Supply Index4.53 (2.92)
Research Growth Index4.70 (4.65)
Search Engine Demand Index40.31 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (31.99)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials13 (16.46%)5.53%
Reviews2 (2.53%)6.00%
Case Studies6 (7.59%)4.05%
Observational0 (0.00%)0.25%
Other58 (73.42%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]